benzyl (R)-(cyano(phenyl)methyl)carbamate

• 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: benzyl (R)-(cyano(phenyl)methyl)carbamate
• 英文别名: benzyl N-[(R)-cyano(phenyl)methyl]carbamate
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: NRGHTWNHDZVHAT-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (R)-(cyano(phenyl)methyl)carbamate 在 盐酸 、 水 作用下， 以 水 为溶剂， 反应 3.0h， 以94%的产率得到左旋苯甘氨酸
  参考文献：
  名称：

  Enantioselective Hydrocyanation of N-Protected Aldimines

  摘要：

  Enantioselective hydrocyanation of N-benzyloxycarbonyl aldimines catalyzed by a Ru[(S)-phgly](2)[(S)-binap]/C6H5OLi system or a bimetallic complex [Li{Ru[(S)-phgly](2)[(S)-binap]}]Cl affords the amino nitriles in 92-99% ee. The reaction is carried out in tert-C4H9OCH3 with a substrate-to-catalyst molar ratio in the range of 500-5000 at -20 to 0 degrees C. Primary, secondary, and tertiary alkyl imines as well as the aryl and heteroaryl substrates are smoothly cyanated to produce the desired products in high yield.

  DOI：

  10.1021/ol203408w
• 作为产物：
  描述：

  苄氧羰酰基苯甘氨酸 在 吡啶 、 二碳酸二叔丁酯 、 ammonium bicarbonate 、 三聚氯氰 作用下， 以 乙腈 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 benzyl (R)-(cyano(phenyl)methyl)carbamate
  参考文献：
  名称：

  An Expedient Route to the Tetrazole Analogues of α-Amino Acids

  摘要：

  [GRAPHIC]Convenient conditions are described for the transformation of alpha-aminonitriles to the tetrazole analogues of alpha-amino acids. Refluxing the starting material in water/2-propanol at 80 degreesC with sodium azide and catalytic zinc bromide affords the tetrazole product in yields generally exceeding 90%.

  DOI：

  10.1021/ol020096x

文献信息

• Retention of stereochemistry in the microwave assisted synthesis of 1H-tetrazole bioisosteric moiety from chiral phenyl-acetic acid derivatives
  作者：Mara Tomassetti、Michela Fanì、Gianluca Bianchini、Sandra Giuli、Andrea Aramini、Sandro Colagioia、Giuseppe Nano、Samuele Lillini

  DOI：10.1016/j.tetlet.2013.09.022

  日期：2013.11

  Chiral substituted phenylethyl-1H-tetrazoles were built-up from the corresponding carboxylic acid derivatives by a useful three-step synthesis. The procedure, that preserves the chiral center from racemization, was successfully applied to a selection of several hit compounds by conversion of the carboxylic acid moiety to the nitrile derivatives and subsequent reaction with trimethylstannyl azide, under microwave conditions. A useful application to the corresponding tetrazole analogue has been found also in the conversion of the aminoacidic moiety like (R)-N-Cbz-phenylglycine showing a wide potential synthetic application. (C) 2013 Elsevier Ltd. All rights reserved.
• Enantioselective Hydrocyanation of <i>N</i>-Protected Aldimines
  作者：Masato Uemura、Nobuhito Kurono、Takeshi Ohkuma

  DOI：10.1021/ol203408w

  日期：2012.2.3

  Enantioselective hydrocyanation of N-benzyloxycarbonyl aldimines catalyzed by a Ru[(S)-phgly](2)[(S)-binap]/C6H5OLi system or a bimetallic complex [LiRu[(S)-phgly](2)[(S)-binap]}]Cl affords the amino nitriles in 92-99% ee. The reaction is carried out in tert-C4H9OCH3 with a substrate-to-catalyst molar ratio in the range of 500-5000 at -20 to 0 degrees C. Primary, secondary, and tertiary alkyl imines as well as the aryl and heteroaryl substrates are smoothly cyanated to produce the desired products in high yield.
• An Expedient Route to the Tetrazole Analogues of α-Amino Acids
  作者：Zachary P. Demko、K. Barry Sharpless

  DOI：10.1021/ol020096x

  日期：2002.7.1

  [GRAPHIC]Convenient conditions are described for the transformation of alpha-aminonitriles to the tetrazole analogues of alpha-amino acids. Refluxing the starting material in water/2-propanol at 80 degreesC with sodium azide and catalytic zinc bromide affords the tetrazole product in yields generally exceeding 90%.