N-<(R)-2-hydroxy-1-phenylethyl>-(S)-α-aminobenzenepropanenitrile | 139224-90-1

• 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: N-<(R)-2-hydroxy-1-phenylethyl>-(S)-α-aminobenzenepropanenitrile
• 英文别名: (R,S)-2-<(2-hydroxy-1-phenylethyl)amino>-3-phenylpropanenitrile；(R,S)-2-[(2-hydroxy-1-phenylethyl)amino]-3-phenylpropanenitrile；(2S)-2-[[(1R)-2-hydroxy-1-phenylethyl]amino]-3-phenylpropanenitrile
• CAS: 139224-90-1
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: URJCLINOALPHPU-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• 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

• 作为产物：
  描述：

  D-苯甘氨醇 以 甲醇 、 氯仿 为溶剂， 反应 9.0h， 生成 N-<(R)-2-hydroxy-1-phenylethyl>-(S)-α-aminobenzenepropanenitrile
  参考文献：
  名称：

  Diastereoselective strecker synthesis using α-phenylglycinol as chiral auxiliary

  摘要：

  Use of alpha-phenylglycinol as chiral auxiliary in Strecker synthesis ensures high diastereoselectivity and its easy removal by oxidative cleavage allows large scale preparation of optically active alpha-amino acids.

  DOI：

  10.1016/0040-4039(91)80544-g

文献信息

• α-phenylglycinol as chiral auxiliary in diastereoselective strecker synthesis of α-amino acids
  作者：T.K. Chakraborty、K. Azhar Hussain、G. Venkat Reddy

  DOI：10.1016/0040-4020(95)00523-b

  日期：1995.8

  The high diastereoselectivity achieved in Strecker synthesis using inexpensive α-phenylglycinol as chiral auxiliary and its facile removal by oxidative cleavage make it an ideal choice for the large scale preparations of optically active α-amino acids specially α-arylglycines present abundantly in glycopeptide antibiotics. A number of chiral amino acids are synthesized following this method. Also molecular

  使用廉价的α-苯基甘氨醇作为手性助剂，在Strecker合成中实现了很高的非对映选择性，并且通过氧化裂解可轻松去除，这使其成为大规模制备旋光性α-氨基酸（尤其是糖肽类抗生素中大量存在的α-芳基甘氨酸）的理想选择。按照这种方法可以合成许多手性氨基酸。还进行了分子力学计算以解释观察到的非对映选择。
• An Efficient and Practical Synthesis of L-α-Amino Acids Using (<i>R</i>)-Phenylglycinol as a Chiral Auxiliary
  作者：Takashi Inaba、Ichiro Kozono、Makoto Fujita、Katsuyuki Ogura

  DOI：10.1246/bcsj.65.2359

  日期：1992.9

  L-α-Amino acids including L-α-arylglycines were conveniently and stereoselectively synthesized via the α-amino carbonitriles given by the Strecker reaction of (R)-2-amino-2-phenylethanol with aldehydes and hydrogen cyanide. The stereoselectivity of these α-amino carbonitriles was thermodynamically controlled.

  包括 L-α-芳基甘氨酸在内的 L-α-氨基酸可以通过 (R)-2-氨基-2-苯基乙醇与醛和氰化氢的 Strecker 反应得到的 α-氨基腈方便地立体选择性地合成。这些α-氨基腈的立体选择性受热力学控制。
• Diastereoselective strecker synthesis using α-phenylglycinol as chiral auxiliary
  作者：T.K. Chakraborty、G.V. Reddy、K. Azhar Hussain

  DOI：10.1016/0040-4039(91)80544-g

  日期：1991.12

  Use of alpha-phenylglycinol as chiral auxiliary in Strecker synthesis ensures high diastereoselectivity and its easy removal by oxidative cleavage allows large scale preparation of optically active alpha-amino acids.