(S)-N-methyl-1-phenyl-2-(piperidin-1-yl)ethanamine | 129380-08-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-N-methyl-1-phenyl-2-(piperidin-1-yl)ethanamine
• 英文别名: (S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine；(1S)-N-methyl-1-phenyl-2-piperidin-1-ylethanamine
• CAS: 129380-08-1
• 化学式: C₁₄H₂₂N₂
• 分子量: 218.342
• InChiKey: WDWBJLRLEYGMMU-CQSZACIVSA-N

物化性质

• 沸点：
  314.6±22.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-cyclooct-2-enone 、 methylcopper 、 (S)-N-methyl-1-phenyl-2-(piperidin-1-yl)ethanamine 生成 3-methylcyclohexanone
  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
• 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-methyl-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

文献信息

• 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。
• Enantioselective conjugate addition to cyclic enones with (S)-mapp-cuprates.
  作者：Bryant E. Rossiter、Masakatsu Eguchi、Amelia E. Herna´ndez、Denise Vickers、John Medich、John Marr、Daniel Heinis

  DOI：10.1016/0040-4039(91)80603-4

  日期：1991.8

  Chiral amidocuprates, formed from CuI, n-butyl or methyl lithium and (S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine, (S)-MAPP, react enantioselectively with 5, 6, 7 and 8-membered cyclic enones to give products with up to 97% e.e. The synthesis of (S)-MAPP is also reported.

  由CuI，正丁基或甲基锂和（S）-N-甲基-1-苯基-2-（1-哌啶基）乙胺，（S）-MAPP形成的手性酰胺基铜酸盐与5、6、7和8元环烯酮可提供高达97％ee的产物还报道了（S）-MAPP的合成。
• Chiral copper amine complexes
  申请人：Brigham Young University

  公开号：US05134238A1

  公开（公告）日：1992-07-28

  Disclosed herein is a class of chiral copper-amine complexes of the formula R(L*) CuLi in which L* is selected from: ##STR1## In this formula, R is a transferable ligand, which can be alkyl, aryl or aralkyl. M is a metal ion such as Li, Na, K, Cs, Rb, Be, Mg and other metal ions from the first two columns of the periodic table. R.sub.1 is straight chain alkyl, R.sub.2 is aryl or substituted aryl and R.sub.3 and R.sub.4 form a heterocyclic ring or a substituted heterocyclic ring with 4 to 8 members including oxygen and sulfur. Such complexes react with .alpha.,.beta.-unsaturated ketones, aldehydes, esters and other carbonyl containing compounds such that R is transferred to the 3 position enantioselectively as shown below. ##STR2## Such complexes react with .alpha.,.beta.-unsaturated ketones in the presence of trialkysilyl halides to give silyl enol ether in which R is substituted in the 3 position as shown below. ##STR3##

  本文揭示了一类手性铜胺络合物，化学式为R（L*）CuLi，其中L*选自：##STR1## 在此公式中，R是可转移的配体，可以是烷基，芳基或芳基烷基。M是金属离子，如Li，Na，K，Cs，Rb，Be，Mg和周期表前两列中的其他金属离子。R.sub.1是直链烷基，R.sub.2是芳基或取代芳基，R.sub.3和R.sub.4形成一个含氧和硫的4至8个成员的杂环或取代杂环。这种络合物与α，β-不饱和酮，醛，酯和其他含羰基的化合物反应，使R在选择性地转移到3位置，如下所示。##STR2## 这种络合物与α，β-不饱和酮在三烷基硅基卤化物存在下反应，生成硅烷基烯醇醚，其中R在3位置被取代，如下所示。##STR3##
• Analgesic compounds and methods of use
  申请人：The Regents of the University of California

  公开号：US10167295B2

  公开（公告）日：2019-01-01

  Provided herein, inter alia, are methods and compositions for achieving an analgesic effect in subjects in need thereof.

  除其他外，本文还提供了用于在有需要的受试者身上实现镇痛效果的方法和组合物。
• ANALGESIC COMPOUNDS AND METHODS OF USE
  申请人：The Regents of the University of California

  公开号：US20160068541A1

  公开（公告）日：2016-03-10

  Provided herein, inter alia, are methods and compositions for achieving an analgesic effect in subjects in need thereof.