Benzenemethanamine, N-(1-cyclohexylethylidene)-, (E)- | 143063-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzenemethanamine, N-(1-cyclohexylethylidene)-, (E)-
• 英文别名: anti-N-(1-cyclohexylethylidene)benzylamine
• CAS: 143063-62-1
• 化学式: C₁₅H₂₁N
• 分子量: 215.338
• InChiKey: AMIHDJXPWWQWRB-DTQAZKPQSA-N

物化性质

• 沸点：
  303.6±21.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  Benzenemethanamine, N-(1-cyclohexylethylidene)-, (E)- 在 diethylzinc polymethylhydrosiloxane 、 N,N'-二苄基乙二胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 18.0h， 以99%的产率得到N-(1-(cyclohexyl)ethyl)benzylamine
  参考文献：
  名称：

  Direct Zn–diamine promoted reduction of CO and CN bonds by polymethylhydrosiloxane in methanol

  摘要：

  在室温下，酮和亚胺在甲醇中通过使用聚甲基氢硅氧烷（PMHS）和简单的锌-胺催化剂，采用一步法化学选择性地还原为相应的醇和胺，并获得高产率。

  DOI：

  10.1039/b210144k
• 作为产物：
  描述：

  乙酰基环己烷 、 苄胺 在 MS 3A 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 Benzenemethanamine, N-(1-cyclohexylethylidene)-, (E)-
  参考文献：
  名称：

  Enantioselective Hydrogenation of Imines with Chiral (Phosphanodihydrooxazole)iridium Catalysts

  摘要：

  AbstractCationic iridium(I) complexes of chiral phosphanodihydrooxazoles were used as catalysts for the enantioselective hydrogenation of prochiral N‐alkyl and N‐aryl imines. The complexes are air‐stable crystalline solids that can be readily prepared and are easy to handle. The structures of two complexes were determined by X‐ray analysis. For N‐alkyl imines of acetophenone, enantiomeric excesses of up to 79% were obtained. Dialkyl ketimines and cyclic imines showed lower reactivity and selectivity. A remarkable dilution effect was observed for the hydrogenation of the N‐phenyl imine of acetophenone: decreasing the substrate and catalyst concentration led to a significant improvement of the enantioselectivity. Thus, up to 89% ee could be achieved using 0.1 mol% of catalyst. The highest enantioselectivities were obtained in weakly coordinating solvents such as CH2Cl2. Additives such as halides, imides, or amines were found to poison the catalyst. Hydrogen pressures of 100 bar were usually employed, but in some cases identical results were achieved with only 1 bar H2.

  DOI：

  10.1002/chem.19970030609

文献信息

• Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: the counteranion and solvent effects, and substrate scope
  作者：Fei Chen、Ziyuan Ding、Yanmei He、Jie Qin、Tianli Wang、Qing-Hua Fan

  DOI：10.1016/j.tet.2012.03.019

  日期：2012.7

  Asymmetric hydrogenation of N-alkyl and N-aryl ketimines catalyzed by chiral cationic η6-arene-(N-monosulfonylated diamine) Ru(II) complexes has been investigated. Strong counteranion and solvent effects on the enantioselectivity were observed. The ruthenium catalyst bearing non-coordinating BArF− anion was found to be particularly effective for the hydrogenation of acyclic and exocyclic N-alkyl ketimines

  的不对称氢化ñ -烷基和Ñ通过催化芳基酮亚胺的手性阳离子η 6 -arene-（Ñ -monosulfonylated二胺）的Ru（II）络合物进行了研究。观察到强烈的抗衡阴离子和溶剂对对映选择性的影响。钌催化剂轴承非配位BARF -阴离子被认为是对无环和环外的氢化特别有效ñ -烷基酮亚胺在（BOC）的存在下2O在二氯甲烷中或什至在无溶剂条件下提供的手性胺，其ee可达99％以上，并具有完全转化率。或者，在不存在（Boc）2 O的情况下，具有手性磷酸根阴离子和相应磷酸作为添加剂的钌催化剂也有效用于N-烷基酮亚胺的氢化，对映选择性和完全转化率优异。对于Ñ -芳基酮亚胺降低通过使用钌催化剂轴承BARF观察对映体过量-阴离子。因此，该催化方案为光学活性胺提供了简便实用的途径，并已成功用于对映体纯的（+）-舍曲林的克级合成中。
• Catalytic Asymmetric Hydrogenation of Imines with a Chiral Titanocene Catalyst: Scope and Limitations
  作者：Christopher A. Willoughby、Stephen L. Buchwald

  DOI：10.1021/ja00099a012

  日期：1994.10

  The asymmetric hydrogenation of imines with a chiral titanocene catalyst derived from Brintzinger's ansatitanocene complex 1 proceeds to afford amines with good to excellent enantioselectivity. The catalyst is particularly effective for the reduction of cyclic imines. For these substrates enantiomeric excesses from 95 to 99% were achieved. For acyclic imines lower enantiomeric excesses were observed. The reason for this is likely due to the fact that the acyclic imines are mixtures of anti and syn isomers which interconvert during the reaction. The catalyst was found to be tolerant of many functional groups found in organic synthesis. Thus the reaction represents an effective method for the synthesis of chiral cyclic amines.
• US5686616A
  申请人：——

  公开号：US5686616A

  公开（公告）日：1997-11-11
• Direct Zn–diamine promoted reduction of CO and CN bonds by polymethylhydrosiloxane in methanol
  作者：Virginie Bette、André Mortreux、Christian W. Lehmann、Jean-François Carpentier

  DOI：10.1039/b210144k

  日期：2003.1.23

  Ketones and imines are chemoselectively reduced at room temperature in methanol to the corresponding alcohols and amines in high yields in a one-step procedure using polymethylhydrosiloxane (PMHS) and a simple zinc–diamine catalyst.

  在室温下，酮和亚胺在甲醇中通过使用聚甲基氢硅氧烷（PMHS）和简单的锌-胺催化剂，采用一步法化学选择性地还原为相应的醇和胺，并获得高产率。
• Enantioselective Hydrogenation of Imines with Chiral (Phosphanodihydrooxazole)iridium Catalysts
  作者：Patrick Schnider、Guido Koch、Roger Prétôt、Guozhi Wang、Frank Michael Bohnen、Carl Krüger、Andreas Pfaltz

  DOI：10.1002/chem.19970030609

  日期：1997.6

  AbstractCationic iridium(I) complexes of chiral phosphanodihydrooxazoles were used as catalysts for the enantioselective hydrogenation of prochiral N‐alkyl and N‐aryl imines. The complexes are air‐stable crystalline solids that can be readily prepared and are easy to handle. The structures of two complexes were determined by X‐ray analysis. For N‐alkyl imines of acetophenone, enantiomeric excesses of up to 79% were obtained. Dialkyl ketimines and cyclic imines showed lower reactivity and selectivity. A remarkable dilution effect was observed for the hydrogenation of the N‐phenyl imine of acetophenone: decreasing the substrate and catalyst concentration led to a significant improvement of the enantioselectivity. Thus, up to 89% ee could be achieved using 0.1 mol% of catalyst. The highest enantioselectivities were obtained in weakly coordinating solvents such as CH2Cl2. Additives such as halides, imides, or amines were found to poison the catalyst. Hydrogen pressures of 100 bar were usually employed, but in some cases identical results were achieved with only 1 bar H2.