(S)-2-benzyl-3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-methylpropionitrile | 607720-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (S)-2-benzyl-3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-methylpropionitrile
• 英文别名: (2S)-2-benzyl-3-(1,3-dioxoisoindol-2-yl)-2-methylpropanenitrile
• CAS: 607720-65-0
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: ANFBCEKYWFHPPT-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  61.17
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-benzyl-3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-methylpropionitrile 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 168.0h， 以86%的产率得到(S)-α-benzyl-α-methyl-β-alanine
  参考文献：
  名称：

  Efficient enantioconvergent synthesis of (S)-α-benzyl-α-methyl-β-alanine from (R)- and (S)-2-cyano-2-methyl-3-phenylpropanoic acid

  摘要：

  An efficient synthesis of (S)-alpha-benzyl-alpha-methyl-beta-alanine in 59% overall yield from benzaldehyde and methyl cyanoacetate has been developed. Enantioconvergent approaches to the synthesis of the target alpha,alpha-disubstituted beta-amino acid from both enantiomers of previously resolved 2-eyano-2-methyl-3-phenylpropanoic acid constitute the key steps in the proposed methodology. The use of inexpensive and readily available reagents and the simplicity of the experimental procedures make the present protocol synthetically attractive and of great potential for scale up. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00443-9
• 作为产物：
  描述：

  (R)-(-)-2-cyano-2-methyl-3-phenylpropionic acid 在 sodium tetrahydroborate 、 caesium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 201.5h， 生成 (S)-2-benzyl-3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-methylpropionitrile
  参考文献：
  名称：

  Efficient enantioconvergent synthesis of (S)-α-benzyl-α-methyl-β-alanine from (R)- and (S)-2-cyano-2-methyl-3-phenylpropanoic acid

  摘要：

  An efficient synthesis of (S)-alpha-benzyl-alpha-methyl-beta-alanine in 59% overall yield from benzaldehyde and methyl cyanoacetate has been developed. Enantioconvergent approaches to the synthesis of the target alpha,alpha-disubstituted beta-amino acid from both enantiomers of previously resolved 2-eyano-2-methyl-3-phenylpropanoic acid constitute the key steps in the proposed methodology. The use of inexpensive and readily available reagents and the simplicity of the experimental procedures make the present protocol synthetically attractive and of great potential for scale up. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00443-9