(2R/S)-3-phenyl-2-<(R)-1-phenylethylamino>propanenitrile | 246522-97-4

• 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: (2R/S)-3-phenyl-2-<(R)-1-phenylethylamino>propanenitrile
• 英文别名: 3-phenyl-2-[(R)-1-phenylethylamino]propanenitrile；3-phenyl-2-[[(1R)-1-phenylethyl]amino]propanenitrile
• CAS: 246522-97-4
• 化学式: C₁₇H₁₈N₂
• 分子量: 250.343
• InChiKey: JWVMFZNKZFXETC-XPCCGILXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  (2R/S)-3-phenyl-2-<(R)-1-phenylethylamino>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-4-phenyl-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 、 苯乙醛 在 sodium metabisulfite 作用下， 以 水 为溶剂， 反应 19.0h， 生成 (2R/S)-3-phenyl-2-<(R)-1-phenylethylamino>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

• Asymmetric synthesis of 3-amino-2-hydroxy-4-phenylbutanoate
  作者：Hyun-Joon Ha、Young-Gil Ahn、Gwan Sun Lee

  DOI：10.1016/s0957-4166(99)00249-9

  日期：1999.6

  Asymmetric synthesis of 3-amino-2-hydroxy-4-phenylbutanoate, a key component of the natural product bestatin and HIV protease inhibitors of KNI-272 and R-87366, has been achieved from the stereoselective aldimine coupling reaction between 3-phenyl-2-aminopropanenitrile and (Z)-alpha-methoxy trimethylsilyl ketene acetal in the presence of Lewis acids. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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)