cyclohexylidene-(1-phenyl-ethyl)-amine | 56424-42-1

• 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: cyclohexylidene-(1-phenyl-ethyl)-amine
• 英文别名: N-[(1R)-1-phenylethyl]cyclohexanimine
• CAS: 56424-42-1
• 化学式: C₁₄H₁₉N
• 分子量: 201.312
• InChiKey: GPHCGSUNNLMMEQ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cyclohexylidene-(1-phenyl-ethyl)-amine 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 生成 2-(1-phenyl-ethyl)-1-oxa-2-aza-spiro[2.5]octane
  参考文献：
  名称：

  Absolute configuration at chiral nitrogen in oxaziridines. 2

  摘要：

  DOI：

  10.1021/jo00444a027
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 环己酮 以 苯 为溶剂， 反应 1.0h， 生成 cyclohexylidene-(1-phenyl-ethyl)-amine
  参考文献：
  名称：

  用环状有机锂（酰胺基）铜酸盐将环状烯酮的对映选择性共轭物，第四部分。配体结构与对映选择性之间的关系

  摘要：

  衍生自伯胺和仲胺的垢性锂酰胺与有机铜化合物在醚或二甲基硫醚中反应，形成能够对2-环烯酮进行对映选择性共轭加成的有机（酰胺基）碳酸锂。最成功的杂铜酸盐，其中手性配体为（S）-N-甲基-1-苯基-2-（1-哌啶基）乙胺，（S） -MAPP，13，与环状烯酮反应生成最高97％ee。观察到由配体13形成的铜酸盐的非线性不对称诱导。

  DOI：

  10.1016/s0040-4020(01)86278-5

文献信息

• Synthesis of Enantiomerically Enriched α-Sulfenylated Ketones and Aldehydes
  作者：Joo-Hack Youn、Rudolf Herrmann、Ivar Ugi

  DOI：10.1055/s-1987-27870

  日期：——

  α-Sulfenylated carbonyl compounds are prepared by the reaction of imines of aldehydes and ketones containing α-hydrogens with disulfides via the metalloenamines. With (R)-α-phenylethylamine as chiral auxiliary, enantiomeric excesses of 13-51% are observed.

  通过含有α-氢的醛和酮的亚胺与二硫化物的反应，利用金属烯胺制备α-硫代羰基化合物。以(R)-α-苯乙胺作为手性辅助剂，观察到13-51%的对映体过量。
• A versatile route to β-enamino esters by acylation of lithium enamines with diethyl carbonate or benzyl chloroformate
  作者：Giuseppe Bartoli、Cristina Cimarelli、Renato Dalpozzo、Gianni Palmieri

  DOI：10.1016/0040-4020(95)00476-o

  日期：1995.7

  route to β-enamino esters 1, using accessible starting materials, was developed. Lithiated enamines are allowed to react with diethyl carbonate or benzyl chloroformate with the formation of the β-enamino esters 1a or 1b. The reaction is rather general from a wide array of ketimines and aldimines. Products included cyclic β-enamino esters 1aa-ac, very useful for the synthesis of natural products.

  开发了一种使用易得的起始原料制备β-烯胺酯1的通用方法。使锂化的烯胺与碳酸二乙酯或氯甲酸苄酯反应，形成β-烯氨基酯1a或1b。来自各种各样的酮亚胺和醛亚胺的反应相当普遍。产品包括环状β-烯胺酯1aa-ac，对合成天然产物非常有用。
• Reaction of cyclohexanones imines with substituted nitroolefins. New synthesis of tetrahydroindole derivatives
  作者：Sethy Lim、Ivan Jabin、Gilbert Revial

  DOI：10.1016/s0040-4039(99)00708-x

  日期：1999.5

  The Michael-type addition of cyclohexanones imines, reacting as their secondary enamine tautomers. to beta-substituted nitroolefins is followed by a cyclization reaction with elimination of the nitro group to afford substituted tetrahydroindoles. When a 2-methylcyclohexanone imine is reacted, an unexpected inversion of the regioselectivity is observed when compared with beta-substituted ethylenic eaters. thus allowing to obtain also substituted tetrahydroindoles (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Bond Rotation Dynamics of <i>N</i>-Cycloalkenyl-<i>N</i>-benzyl α-Haloacetamide Derivatives
  作者：David B. Guthrie、Krishnan Damodaran、Dennis P. Curran、Paul Wilson、Andrew J. Clark

  DOI：10.1021/jo900491w

  日期：2009.6.5

  Barriers to rotation of the N-alkenyl bond in a series of N-cycloalkenyl-N-benzyl alpha-haloacetamide derivatives have been measured by variable-temperature NMR experiments. The barriers range from 10 to 18 kcal/mol, depending on ring size and on substituents on the cycloalkene and the amide. The observed trends aid in the design of substituent combinations that provide resolvable enantiomers or diastereomers at ambient temperature. The compounds undergo 4-exo and 5-endo radical cyclizations at rates that may be faster or slower than the estimated rate of N-alkenyl bond rotation in the derived radicals, depending on the substituents.
• A novel approach to chiral spirodiaziridines
  作者：Stefania Fioravanti、Lauso Olivieri、Lucio Pellacani、Paolo A. Tardella

  DOI：10.1016/s0040-4039(98)01317-3

  日期：1998.8

  Imines in the presence of NsONHCO(2)Et give diaziridines at room temperature in good yields and with good diastereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.