(S)-N-benzyl-1-phenyl-2-(piperidin-1-yl)ethanamine

• 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: (S)-N-benzyl-1-phenyl-2-(piperidin-1-yl)ethanamine
• 英文别名: benzyl-(1-phenyl-2-piperidin-1-yl-ethyl)-amine；(S)-N-benzyl-1-phenyl-2-(1-piperidinyl)ethanamine；(1S)-N-benzyl-1-phenyl-2-piperidin-1-ylethanamine
• 化学式: C₂₀H₂₆N₂
• 分子量: 294.44
• InChiKey: XWJKVBWFCZPRJJ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-(+)-扁桃酸 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 copper dichloride 作用下， 以 四氢呋喃 、 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 57.0h， 生成 (S)-N-benzyl-1-phenyl-2-(piperidin-1-yl)ethanamine
  参考文献：
  名称：

  Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

  摘要：

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00376-9
• 作为试剂：
  描述：

  三甲基氯硅烷 、 (S)-[(S)-3-methylcyclohex-2-enyl] 2-methylbutanoate 在 正丁基锂 、 (S)-N-benzyl-1-phenyl-2-(piperidin-1-yl)ethanamine 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 (S)-2-methyl-2-[(R)-1-methylcyclohex-2-enyl]butanoic acid 、 (R)-2-methyl-2-[(R)-1-methylcyclohex-2-enyl]butanoic acid
  参考文献：
  名称：

  通过爱尔兰-克莱森重排立体选择性构建相邻第四元手性中心：环醇酯的立体选择

  摘要：

  这项工作描述了对衍生自环醇酯的 α,α-二取代烯醇化物的爱尔兰-克莱森重排的研究。通过匹配酯和碱的手性，使用 N-苄基 Koga 型碱通常可以实现高度立体选择性烯醇化。(3,3)-sigmatropic 重排以良好的产率和适度的非对映选择性发生，形成两个相邻的四元立体中心，并且通常通过椅子状过渡态进行。

  DOI：

  10.1055/s-0029-1219965

文献信息

• Enantioselective conjugate addition to cyclic enones with scalemic lithium organo(amido)cuprates, Part IV. Relationship between ligand structure and enantioselectivity
  作者：Bryant E. Rossiter、Masakatsu Eguchi、Guobin Miao、Nicole M. Swingle、Amelia E. Hernández、Denise Vickers、Ezdan Fluckiger、R. Greg Patterson、K. Vásavi Reddy

  DOI：10.1016/s0040-4020(01)86278-5

  日期：1993.1

  Scalemic lithium amides derived from primary and secondary amines react with organocopper compounds in ether or dimethyl sulfide to form lithium organo(amido)cuprates capable of enantioselective conjugate addition to 2-cycloalkenones. The most successful heterocuprate, in which the chiral ligand is (S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine, (S)-MAPP, 13, reacts with cyclic enones to form products

  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。
• An Efficient Synthesis of Chiral Nonracemic Diamines: Application in Asymmetric Synthesis
  作者：Parthasarathy Saravanan、Vinod K Singh

  DOI：10.1016/s0040-4039(97)10578-0

  日期：1998.1

  A variety of chiral diamines have been synthesized from optically active mandelic acid in an efficient manner. The chiral nonracemic lithium amide base derived from one of the diamines has been used in formal asymmetric synthesis of natural products such as (−)-utenone A and (−)-carbovir. © 1997 Elsevier Science Ltd. All rights reserved.

  已经从旋光的扁桃酸中有效地合成了各种手性二胺。衍生自一种二胺的手性非外消旋锂酰胺碱已用于天然产物如（-）-泛酮A和（-）-carbovir的形式不对称合成。©1997 Elsevier ScienceLtd。保留所有权利。
• The preparation of β-substituted amines from mixtures of epoxide opening products via a common aziridinium ion intermediate
  作者：Shelby R. Anderson、Joshua T. Ayers、Keith M. DeVries、Fumitaka Ito、Debra Mendenhall、Brian C. Vanderplas

  DOI：10.1016/s0957-4166(99)00243-8

  日期：1999.7

  Here we describe a one-pot synthesis of a series of beta-substituted amines as single enantiomers from an initial regioisomeric mixture of styrene oxide ring-opening products. We also report the isolation and characterization of a key beta-chloro intermediate and provide additional insight into the mechanism of the reported alkylations. These results require that the reaction proceeds through a common aziridinium ion intermediate on two separate occasions in order to account for the observed overall net retention of configuration in proceeding from (S)-styrene oxide to the desired beta-substituted amine products. (C) 1999 Elsevier Science Ltd. All rights reserved.
• PROCESS FOR MAKING SUBSTITUTED 2-AMINO-THIAZOLONES
  申请人：Moniz George A.

  公开号：US20100280255A1

  公开（公告）日：2010-11-04

  The present invention relates to methods of making compounds that inhibit 11-hydroxysteroid dehydrogenase type 1 enzyme (11-HSD1). One method comprises (a) contacting a compound of formula (II) sequentially with a chiral base in the presence of an amine, and an alkylating agent R3-LG, (b) contacting the product of (a) with an acid to form a salt, and (c) reacting the salt with a base to form the compound of formula (I), wherein Z, R1, R2, and R3 are defined herein.
• Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes
  作者：P Saravanan、Alakesh Bisai、S Baktharaman、M Chandrasekhar、Vinod K Singh

  DOI：10.1016/s0040-4020(02)00376-9

  日期：2002.6

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.