[((1S,2R)-2-Chloro-1-methyl-2-phenyl-ethyl)-methyl-amino]-acetonitrile | 452096-18-3

• 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: [((1S,2R)-2-Chloro-1-methyl-2-phenyl-ethyl)-methyl-amino]-acetonitrile
• 英文别名: 2-[[(1R,2S)-1-chloro-1-phenylpropan-2-yl]-methylamino]acetonitrile
• CAS: 452096-18-3
• 化学式: C₁₂H₁₅ClN₂
• 分子量: 222.718
• InChiKey: WMXKOAWAUMCFIF-JQWIXIFHSA-N

物化性质

• 沸点：
  315.3±32.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [((1S,2R)-2-Chloro-1-methyl-2-phenyl-ethyl)-methyl-amino]-acetonitrile 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以84%的产率得到(5R,6S)-6,7-dimethyl-5-phenyl-5,6,7,8-tetrahydro-tetrazolo[1,5-a]pyrazine
  参考文献：
  名称：

  Expeditive synthesis of homochiral fused tri- and tetrazoles–piperazines from β-amino alcohols

  摘要：

  N-Cyanomethyl and N-propargyl beta-amino alcohols are chlorinated with SOCl2 and treated with NaN3 in DMSO. A Substitution/cycloaddition process affords in good yields, with high diastereoselectivity and a regioselectivity depending on the substitution pattern of the starting amino alcohol, fused tri- and tetrazoles-pipci-azines. These heterocycles were further lithiated with n-BuLi at the benzylic position and reacted diastereoselectively with a range of electrophiles. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.092
• 作为产物：
  描述：

  麻黄碱 在 氯化亚砜 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 [((1S,2R)-2-Chloro-1-methyl-2-phenyl-ethyl)-methyl-amino]-acetonitrile
  参考文献：
  名称：

  由β-氨基醇直接合成对映体纯的2-氰基氮杂环丁烷

  摘要：

  用β-氨基醇高收率制备对映体纯的2-氰基氮杂环丁烷。已证明该合成是一般性的，并且基于两个重要步骤：（i）N-氰基甲基化的β-氨基醇的氯化和（ii）通过锂化的α-氨基腈的烷基化进行的4- exo - trig闭环。当使用麻黄碱衍生的β-氨基醇时，前一步是立体选择性的。在衍生自苯基甘醇的β-氨基醇的情况下，该步骤还涉及重排。

  DOI：

  10.1016/s0957-4166(02)00076-9

文献信息

• N-Cyanomethyl-β-chloroamines: a convenient source of aziridinium ions
  作者：François Couty、Gwilherm Evano、Damien Prim

  DOI：10.1016/j.tetlet.2005.02.016

  日期：2005.3

  N-Cyanomethyl-β-chloroamines smoothly react with a range of alcohols or amines to give regio- and stereoselectively 1,2-aminoethers or 1,2-diamines. The reaction proceeds through the formation of an intermediate aziridinium ion. The N-cyanomethyl group can then be cleaved easily.

  N-氰甲基-β-氯胺能与多种醇或胺平稳反应，生成区域和立体选择性的1,2-氨基醚或1,2-二胺。反应通过形成中间体叠氮鎓离子而进行。该Ñ氰基可以很容易地切割。
• N-Cyanomethyl-β-chloro amines: chiral building blocks for the synthesis of azacrown ethers
  作者：François Couty、Gwilherm Evano、Laurence Menguy、Vincent Steimetz、Mathieu Toumi

  DOI：10.1016/j.tetlet.2006.05.046

  日期：2006.7

  (1R,2S)-Ephedrine and norephedrine derived N-cyanomethyl-beta-chloro amines react with tri-, tetra- and penta-ethylene glycol to stereoselectively give the corresponding amino ethers. Further transformation into chiral monoaza 12-, 15- and 18-crown-4, -5 and -6 ethers was realized in three steps and good overall yields by: (i) mesylation, (ii) deprotection of the N-cyanomethyl group and (iii) intramolecular alkylation. Binding affinities of these azacrown ethers for alkali cations was studied by FAB-MS. (c) 2006 Elsevier Ltd. All rights reserved.

  （1R,2S)-麻黄碱和去甲麻黄碱衍生的N-氰甲基-β-氯化胺与三、四和五乙二醇反应，具有立体选择性地生成相应的氨基醚。进一步通过三步反应（i）甲基化，（ii）脱去N-氰甲基保护基，（iii）分子内烷基化，以良好的整体收率实现了手性单氮12-, 15-和18-冠-4, -5和-6醚的合成。采用FAB-MS研究了这些氮冠醚对碱金属阳离子的结合亲和力。（c）2006 Elsevier Ltd.版权所有。
• Alkylation of indoles by aziridinium ions: new rapid access to tetrahydro-β-carbolines (THBCs)
  作者：Laurence Menguy、Cheikh Lo、Jérôme Marrot、François Couty

  DOI：10.1016/j.tet.2014.05.009

  日期：2014.7
• A straightforward synthesis of enantiopure 2-cyano azetidines from β-amino alcohols
  作者：Claude Agami、François Couty、Gwilherm Evano

  DOI：10.1016/s0957-4166(02)00076-9

  日期：2002.3

  Enantiopure 2-cyano azetidines were prepared in high yields from β-amino alcohols. This synthesis was shown to be general and is based on two important steps: (i) chlorination of a N-cyanomethylated β-amino alcohol and (ii) a 4-exo-trig ring closure through the alkylation of a lithiated α-amino nitrile. The former step is stereoselective when ephedrine-derived β-amino alcohols are used. In the case

  用β-氨基醇高收率制备对映体纯的2-氰基氮杂环丁烷。已证明该合成是一般性的，并且基于两个重要步骤：（i）N-氰基甲基化的β-氨基醇的氯化和（ii）通过锂化的α-氨基腈的烷基化进行的4- exo - trig闭环。当使用麻黄碱衍生的β-氨基醇时，前一步是立体选择性的。在衍生自苯基甘醇的β-氨基醇的情况下，该步骤还涉及重排。
• Expeditive synthesis of homochiral fused tri- and tetrazoles–piperazines from β-amino alcohols
  作者：François Couty、François Durrat、Damien Prim

  DOI：10.1016/j.tetlet.2004.03.092

  日期：2004.5

  N-Cyanomethyl and N-propargyl beta-amino alcohols are chlorinated with SOCl2 and treated with NaN3 in DMSO. A Substitution/cycloaddition process affords in good yields, with high diastereoselectivity and a regioselectivity depending on the substitution pattern of the starting amino alcohol, fused tri- and tetrazoles-pipci-azines. These heterocycles were further lithiated with n-BuLi at the benzylic position and reacted diastereoselectively with a range of electrophiles. (C) 2004 Elsevier Ltd. All rights reserved.