[1S,2R,(S)]-N-cyano(phenyl)methyl-1-aminoindan-2-ol | 740845-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: [1S,2R,(S)]-N-cyano(phenyl)methyl-1-aminoindan-2-ol
• 英文别名: (2S)-2-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino]-2-phenylacetonitrile
• CAS: 740845-56-1
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: DIEZMSFBBVMAOR-ZACQAIPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  56
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1S,2R,(S)]-N-cyano(phenyl)methyl-1-aminoindan-2-ol 以 二甲基亚砜 为溶剂， 反应 168000.0h， 生成 [1S,2R,(R)]-N-cyano(phenyl)methyl-1-aminoindan-2-ol
  参考文献：
  名称：

  Epimerization of Diastereomeric α-Amino Nitriles to Single Stereoisomers in the Solid State

  摘要：

  [GRAPHICS]A diastereomeric mixture of the alpha-amino nitrile prepared by the Strecker reaction of benzaldehyde, (1 S,2R)-1-aminoindan-2-ol, and cyanotrimethylsilane thermally epimerizes in the solid state to give a single diastereomer with an (S)-configuration at the a position to the nitrile moiety. This shows a sharp contrast to the reaction conducted in DMSO at room temperature, which gives a 1:1 mixture of (S)- and (R)-isomers. Several other a-amino nitriles also epimerize in the solid-state toward single diastereomers.

  DOI：

  10.1021/ol049256q
• 作为产物：
  描述：

  (S)-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-indan-1-ylamino]-phenyl-acetonitrile 生成 [1S,2R,(S)]-N-cyano(phenyl)methyl-1-aminoindan-2-ol
  参考文献：
  名称：

  Epimerization of Diastereomeric α-Amino Nitriles to Single Stereoisomers in the Solid State

  摘要：

  [GRAPHICS]A diastereomeric mixture of the alpha-amino nitrile prepared by the Strecker reaction of benzaldehyde, (1 S,2R)-1-aminoindan-2-ol, and cyanotrimethylsilane thermally epimerizes in the solid state to give a single diastereomer with an (S)-configuration at the a position to the nitrile moiety. This shows a sharp contrast to the reaction conducted in DMSO at room temperature, which gives a 1:1 mixture of (S)- and (R)-isomers. Several other a-amino nitriles also epimerize in the solid-state toward single diastereomers.

  DOI：

  10.1021/ol049256q

文献信息

• Racemic [1SR,2RS,(RS)]-N-cyano(phenyl)methyl-1-aminoindan-2-ol: crystal structure and reactivity towards thermal epimerization in the solid state
  作者：Rumiko Sakurai、Osamu Itoh、Akira Uchida、Tetsutaro Hattori、Sotaro Miyano、Masanori Yamaura

  DOI：10.1016/j.tet.2004.08.084

  日期：2004.11

  A diastereomeric mixture of racemic α-amino nitriles [1SR,2RS,(SR)]- (1) and [1SR,2RS,(RS)]-N-cyano(phenyl)methyl-1-aminoindan-2-ol (2) was thermally epimerized in the solid state to give diastereopure [1SR,2RS,(SR)]-1. The reaction was about 26 times slower than the same reaction of a mixture of their enantiopure counterparts, showing that different mechanisms operated between the two transformations

  外消旋α-氨基腈[1 SR，2RS，（SR）]-（1）和[1 SR，2 RS，（RS）]- N-氰基（苯基）甲基-1-氨基茚满-2-的非对映异构体混合物固态将醇（2）热差向异构体生成非对映异构体[1 SR，2 RS，（SR）]- 1。该反应比对映体纯对映体混合物的相同反应慢约26倍，表明两次转化之间存在不同的机理。X射线晶体分析揭示，在前者的转化，外消旋化合物晶体2被转换成的砾岩晶体1，而在后者中，对映异构体的晶体2被转换成的对映体的晶体1。外消旋和对映纯混合物之间对差向异构化的反应性差异可以通过化合物2在两种晶型中的稳定性差异来合理化。