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1. 酮类还原
由向山，Yamada和同事开发的旋光性酮亚胺钴(II)配合物的不对称还原法很有可能成为获得光学活性醇的一个很简便流行经济的方法。
不对称还原法很简单,胆色素中加入1 mol%的(S)-MPAC, 使用经过四氢化呋喃甲醇和乙醇预先处理过的硼氢化物还原2,2-二甲基-1-四氢萘酮，得到产品(S)-2,2-二甲基-1-四氢萘醇，产率为96%，91%e.e.. 此外,在(S)-MPAC的参与下，(S)-2-甲基-1-四氢萘酮被优先还原为(1S,2S)-2-甲基-1-四氢萘醇，未参加反应的(R)-2-甲基-1-四氢萘酮可以除去。因此，可以进行α-取代羰基化合物的动力学光学分割。
2.光学活性1,3-二醇的合成
1,3-二芳基-1,3-丙二醇和它的衍生物因其作为手性助剂或者是手性配合物来源的用途，广为人知。1,3-二酮利用金属锗配合物催化剂的不对称氢化作用来生产二醇。由于这个反应需要高压环境，所以更为简便的方法接待解决。
Yamada和同事已经证实1,3-二芳基-1,3-丙二酮利用光学活性酮亚胺钴(II)配合物作为催化剂，硼氢化钠做氢化来源，能够实现高外消旋选择性和对映体选择性还原。当使用AMAC(不对称碳原子上有一个三甲苯基基团)时，可以得到具有高外消旋选择性和对映体选择性的1,3-二醇。
这个不对称还原方法非常简单，提纯操作方便。当1,3-二苯基-1,3-丙二酮被用来作为基质材料时，还原产物从乙酸乙酯中从结晶出来。光学纯1,3-二苯基-1,3-丙二醇大概可以得到近60%的产量。
3.光学活性反式-羟醛缩合化合物的合成
光学活性反式-羟醛缩合化合物合成，一些有效的方法包括Abiko,Masamune和其同事利用手性助剂的合成方法已经报道。Yamada和同事已经论证了由克莱森缩合反应而得的2-取代基-1,3-二羰基化合物不对称还原反应生成反式-羟醛缩合化合物。比如：2-甲基-1,3-二苯基-1,3-丙二酮，加入5 mol%AMAC,预先处理过的硼氢化钠还原生成3-羟基酮。
为了推广这个反应，反应也可应用在2-取代基-1-烷基-1,3-二酮的还原中。3-羟基酮可以从2,4-二甲基-1-苯基-1,3-丙二酮而得，产率为46%，伴有99%的化学选择性，99%反式-选择性产品，99%e.e.两个通常认知的2-取代-1-烷基-3-芳基-丙二酮部分不对称还原反应是利用Ru-BINAP 配合物做催化剂还原反应和利用光学活性Ru-配合物请转移反应。在这些例子中，烷基边上的羰基空间位阻小被还原。另一方面，利用酮亚胺钴(II)配合物还原的烷基边上的羰基基团的方法经Yamada和同事进一步研究，效率更高。
此外，Yamada和同事将这个还原方法应用到2-取代-3-酮酸酯中，并且已经报道了其动态动力学拆分原理。根据这个，2-甲基-3-(2-萘基)-3-羰基丙酸乙酯生产出光学活性3-羟基-2-甲基-3-(2-萘基)丙酸乙酯，91%产率，92%反式-选择性产品，95%e.e.
4.胺的还原
1 mol%的(S)-MPAC，N-磷亚胺被四氢化呋喃甲醇、乙醇处理过的硼氢化钠还原，产物(S)- N-磷酰胺基，产率很高，光学纯度高。比如：N-二苯基磷酰-1,2,3,4-四氢-1-萘亚胺还原得到相应的 (S)- N-磷酰胺产率88%-92%。
N-磷酰胺中的磷酰基温和的条件下可以移除，得到光学活性胺，光学纯度为亏损。
5.α,β-不饱和胺的1,4-还原
0.5mol%的(S)-MPAC，四氢化呋喃-2-甲醇预先处理过的硼氢化钠，还原(Z)-3-环己基-2-丁烯酰胺，产物(S)-丁基酰胺，产率99%。91%e.e. (E) -丁烯酰胺时产物(R)-丁基酰胺.
总之，光学活性酮亚胺钴(II)配合物做催化剂的还原反应，在温和条件下使用硼氢化钠即可完成，这是获得高光学纯度的一个极为有效的还原试剂。因此，它可以合成光学活性醇、胺、1,3-二醇、3-羟基羰基化合物、β-不饱和胺等化学品，已经逐渐引起广泛的关注。
| 中文名 | N,N'-双[2-均三甲基苯酰)-3-氧代丁烯基]-(1S,2S)-1,2-二苯基乙二胺合钴(II) |
|---|---|
| 英文名 | (1S,2S)-N,N'-Bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]-1,2-diphenylethylenediaminato Cobalt(II) |
| 中文别名 |
(1S,2S)-N,N'-双[3-氧代-2-(2,4,6-三甲基苯酰)丁烯基]-1,2-二苯基乙二胺合钴(II)
(1S,2S)-N,N’-双[3-氧代-2-(2,4,6-三甲基苯酰)丁烯基]-1,2-二苯基乙二胺合钴(II) (1S,2S)-N,N'-双[3-氧代-2-(2,4,6-三甲基苯酰)亚丁基]-1,2-二苯基乙二胺合钴(II) N,N'-双[2-均三甲基苯酰)-3-氧代丁烯基]-(1S,2S)-1,2-二苯基乙二胺合钴 |
| 英文别名 |
Bisoxotrimethylbenzoylbutylidene
N,N'-Bis[2-(mesitoyl)-3-oxobutylidene]-(1S,2S)-1,2-diphenylethylenediaminato Cobalt(II) MFCD01321132 |
| 分子式 | C42H42CoN2O4 |
|---|---|
| 分子量 | 697.72700 |
| 精确质量 | 697.24800 |
| PSA | 77.32000 |
| LogP | 8.60780 |
| 储存条件 | 室温 |
| 更多 | 1.性状：黄色-深红黄色晶体粉末 |
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(1S,2S)-N,N'-Bis[3-oxo-2-(2,4,6-
Revision number: 1
trimethylbenzoyl)butylidene]-1,2- diphenylethylenediaminato Cobalt(II) SAFETY DATA SHEET Section1. BASE INFORMATION Product name:(1S,2S)-N,N'-Bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]-1,2- diphenylethylenediaminato Cobalt(II)
Revision number:1 Section2. HAZARDS IDENTIFICATION Classification of the GHS PHYSICAL HAZARDSNot classified HEALTH HAZARDS CarcinogenicityCategory 2 ENVIRONMENTAL HAZARDSNot classified GHS label elements Pictograms or hazard symbols Signal wordWarning Hazard statementSuspected of causing cancer Precautionary statements [Prevention]Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Use personal protective equipment as required. [Response]IF exposed or concerned: Get medical advice/attention. [Storage]Store locked up. [Disposal]Dispose of contents/container through a waste management company authorized by the local government Section3. COMPOSITION/INFORMATION ON INGREDIENTS Substance Substance/mixture: Component(s):(1S,2S)-N,N'-Bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]-1,2- diphenylethylenediaminato Cobalt(II) Percent:.... CAS Number:171200-71-8 Synonyms:N,N'-Bis[2-(mesitoyl)-3-oxobutylidene]-(1S,2S)-1,2-diphenylethylenediaminato Cobalt(II) , (S)-MPAC Chemical Formula:C42H42CoN2O4 Section4. FIRST AID MEASURES Inhalation:Remove victim to fresh air and keep at rest in a position comfortable for breathing. Get medical advice/attention. (1S,2S)-N,N'-Bis[3-oxo-2-(2,4,6- trimethylbenzoyl)butylidene]-1,2- diphenylethylenediaminato Cobalt(II) Section4. FIRST AID MEASURES Skin contact:Remove/Take off immediately all contaminated clothing. Gently wash with plenty of soap and water. Get medical advice/attention. Eye contact:Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Get medical advice/attention. Ingestion:Get medical advice/attention.Rinse mouth. Protection of first-aiders:A rescuer should wear personal protective equipment, such as rubber gloves and air- tight goggles. Section5. FIRE-FIGHTING MEASURES Suitable extinguishingDry chemical, foam, water spray, carbon dioxide. media: Specific hazards:Take care as it may decompose upon combustion or in high temperatures to generate poisonous fume. Specific methods:Fire-extinguishing work is done from the windward and the suitable fire-extinguishing method according to the surrounding situation is used. Uninvolved persons should evacuate to a safe place. In case of fire in the surroundings: Remove movable containers if safe to do so. Special protectiveWhen extinguishing fire, be sure to wear personal protective equipment. equipment for firefighters: Section6. ACCIDENTAL RELEASE MEASURES Use extra personal protective equipment (P3 filter respirator for toxic particles). Keep Personal precautions, protective equipment and people away from and upwind of spill/leak. Entry to non-involved personnel should emergency procedures: be controlled around the leakage area by roping off, etc. Environmental precautions: Prevent product from entering drains. Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it. containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with up: appropriate laws and regulations. Section7. HANDLING AND STORAGE Handling Technical measures:Handling is performed in a well ventilated place. Wear suitable protective equipment. Prevent dispersion of dust. Wash hands and face thoroughly after handling. Use a closed system if possible. Use a local exhaust if dust or aerosol will be generated. Advice on safe handling:Avoid all contact! Storage Storage conditions:Keep container tightly closed. Store in a cool and dark place. Store locked up. Store away from incompatible materials such as oxidizing agents. Packaging material:Law is followed. Section8. EXPOSURE CONTROLS / PERSONAL PROTECTION Engineering controls:Install a closed system or local exhaust. Also install safety shower and eye bath. Personal protective equipment Respiratory protection: Dust respirator, self-contained breathing apparatus(SCBA), supplied air respirator, etc. Use respirators approved under appropriate government standards and follow local and national regulations. Hand protection:Impervious gloves. Eye protection:Safety goggles. A face-shield, if the situation requires. Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires. Section9. PHYSICAL AND CHEMICAL PROPERTIES Physical state (20°C):Solid (1S,2S)-N,N'-Bis[3-oxo-2-(2,4,6- trimethylbenzoyl)butylidene]-1,2- diphenylethylenediaminato Cobalt(II) Section9. PHYSICAL AND CHEMICAL PROPERTIES Form:crystal - powder Color:Yellow - Deep reddish yellow Odor:No data available pH: No data available Melting point/freezing point:No data available Boiling Point/Range:No data available Flash Point:No data available Explosive limits Lower:No data available Upper:No data available Density:No data available Solubility:No data available Section10. STABILITY AND REACTIVITY Stable under proper conditions. Stability: Reactivity:No special reactivity has been reported. Incompartible materials: oxidizing agents Hazardous Decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx) Products: Section11. TOXICOLOGICAL INFORMATION Acute Toxicity:No data available Skin corrosion/irritation: No data available Serious eyeNo data available damage/irritation: Germ cell mutagenicity: No data available Carcinogenicity: IARC =Group 2B (Possibly carcinogenic to humans) . NTP =No data available Reproductive toxicity:No data available Section12. ECOLOGICAL INFORMATION Ecotoxicity: No data available Fish: Crustacea:No data available No data available Algae: Persistence / degradability: No data available No data available Bioaccumulative potential(BCF): Mobillity in soil log Pow:No data available No data available Soil adsorption (Koc): Henry's LawNo data available constant(PaM3/mol): Section13. DISPOSAL CONSIDERATIONS Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all federal, state and local regulations when disposing of the substance. Section14. TRANSPORT INFORMATION Hazards Class:Does not correspond to the classification standard of the United Nations Not Listed UN-No: (1S,2S)-N,N'-Bis[3-oxo-2-(2,4,6- trimethylbenzoyl)butylidene]-1,2- diphenylethylenediaminato Cobalt(II) Section15. REGULATORY INFORMATION Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were prescribed. SECTION 16 - ADDITIONAL INFORMATION N/A |
| 危害码 (欧洲) | Xn |
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首先将1,3-二羰基化合物的活性亚甲基甲酰化，然后在光学活性 1,2-二芳基乙二胺作用下得到光学活性酮亚胺配体，配体与甲醇钠、二氯化钴作用生成光学活性酮亚胺钴(II)配合物。具体步骤如图所示：