2-[[(1R)-1-phenylethyl]amino]propanenitrile | 389631-33-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[[(1R)-1-phenylethyl]amino]propanenitrile
• CAS: 389631-33-8
• 化学式: C₁₁H₁₄N₂
• 分子量: 174.246
• InChiKey: GJCIYUBEISDBDK-QVDQXJPCSA-N

物化性质

• 沸点：
  300.1±17.0 °C(Predicted)
• 密度：
  0.995±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[[(1R)-1-phenylethyl]amino]propanenitrile 在 四氯化钛 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 ethyl (2R,3R)-3-acetyloxy-2-[(R)-1-phenylethylamino]butanoate
  参考文献：
  名称：

  New synthesis and ring opening of cis-3-alkylaziridine-2-carboxylates

  摘要：

  Syntheses of cis-3-alkylaziridine-2-carboxylates including cis-3-benzyl- and cis-3-phenylaziridine-2-carboxylates were achieved from the reaction of alpha -aminonitrile and alkyldiazoacetate in the presence of a Lewis acid. Asymmetric version of this reaction with the chiral alpha -methylbenzylamine was also successful for the preparation of chiral aziridines that were used for the synthesis of various amino acids including homophenylalanine, beta -amino-alpha -hydroxy acid, alpha,beta -diamino acid, and alpha -amino-beta -hydroxy acid via regioselective aziridine ring openings. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00823-7
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 氰化钾 、 乙醛 在 sodium metabisulfite 作用下， 以 水 为溶剂， 反应 19.0h， 生成 2-[[(1R)-1-phenylethyl]amino]propanenitrile
  参考文献：
  名称：

  乙烯与取代的同手性 2(1H)-吡嗪酮的非对映选择性 Diels-Alder 加成

  摘要：

  介绍了乙烯与带有同手性辅助基团的 2(1H)-吡嗪酮的 Diels-Alder 反应。环加成产物形成的非对映体过量高达 50%。据我们所知，这些是第一次与乙烯的 Diels-Alder 反应，显示出一定程度的非对映选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200600805

文献信息

• New synthesis and ring opening of cis-3-alkylaziridine-2-carboxylates
  作者：Kwang-Deuk Lee、Jang-Min Suh、Jae-Hoon Park、Hyun-Joon Ha、Hwan Gun Choi、Chan Sun Park、Jae Won Chang、Won Koo Lee、Yongkwan Dong、Hoseop Yun

  DOI：10.1016/s0040-4020(01)00823-7

  日期：2001.9

  Syntheses of cis-3-alkylaziridine-2-carboxylates including cis-3-benzyl- and cis-3-phenylaziridine-2-carboxylates were achieved from the reaction of alpha -aminonitrile and alkyldiazoacetate in the presence of a Lewis acid. Asymmetric version of this reaction with the chiral alpha -methylbenzylamine was also successful for the preparation of chiral aziridines that were used for the synthesis of various amino acids including homophenylalanine, beta -amino-alpha -hydroxy acid, alpha,beta -diamino acid, and alpha -amino-beta -hydroxy acid via regioselective aziridine ring openings. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Diastereoselective Diels–Alder Additions of Ethene to Substituted Homochiral 2(1H)-Pyrazinones
  作者：Jo Alen、Wim J. Smets、Liliana Dobrzańska、Wim M. De Borggraeve、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1002/ejoc.200600805

  日期：2007.2

  Diels–Alder reactions of ethene with 2(1H)-pyrazinones bearing a homochiral auxiliary group are presented. The cycloaddition products form with diasteromeric excesses of up to 50 %. To the best of our knowledge, these are the firstDiels–Alder reactions with ethene showing some degree of diastereoselectivity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  介绍了乙烯与带有同手性辅助基团的 2(1H)-吡嗪酮的 Diels-Alder 反应。环加成产物形成的非对映体过量高达 50%。据我们所知，这些是第一次与乙烯的 Diels-Alder 反应，显示出一定程度的非对映选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)