(1R,2R,1'S)-1-[(1'-methylbenzyl)amino]-2-iso-propylcyclobutanecarboxamide | 587829-73-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2R,1'S)-1-[(1'-methylbenzyl)amino]-2-iso-propylcyclobutanecarboxamide
• 英文别名: (1R,2R)-1-[[(1S)-1-phenylethyl]amino]-2-propan-2-ylcyclobutane-1-carboxamide
• CAS: 587829-73-0
• 化学式: C₁₆H₂₄N₂O
• 分子量: 260.379
• InChiKey: CNJPDKSFJJPWAH-JGGQBBKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,1'S)-1-[(1'-methylbenzyl)amino]-2-iso-propylcyclobutanecarboxamide 在 palladium dihydroxide 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 4.0h， 以95%的产率得到(1R,2R)-1-amino-2-isopropylcyclobutanecarboxamide
  参考文献：
  名称：

  First synthesis of (1S,2S)- and (1R,2R)-1-amino-2-isopropylcyclobutanecarboxylic acids by asymmetric Strecker reaction from 2-substituted cyclobutanones

  摘要：

  An efficient and easy one-pot reaction from readily available racemic 2-substituted cyclobutanones gave, by means of asymmetric Strecker synthesis in the presence of an amine chiral auxiliary, two major aminonitriles with excellent diastereoselectivity. After separation, the major cis-aminonitriles were hydrolysed and hydrogenolysed to lead for the first time to pure non-racemic (+)-1-amino-2-isopropylcyclobutanecarboxylic acid (ACBC) and its antipode. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00073-9
• 作为产物：
  描述：

  2-isopropylcyclobutanone 在 硫酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 96.0h， 生成 (1R,2R,1'S)-1-[(1'-methylbenzyl)amino]-2-iso-propylcyclobutanecarboxamide
  参考文献：
  名称：

  First synthesis of (1S,2S)- and (1R,2R)-1-amino-2-isopropylcyclobutanecarboxylic acids by asymmetric Strecker reaction from 2-substituted cyclobutanones

  摘要：

  An efficient and easy one-pot reaction from readily available racemic 2-substituted cyclobutanones gave, by means of asymmetric Strecker synthesis in the presence of an amine chiral auxiliary, two major aminonitriles with excellent diastereoselectivity. After separation, the major cis-aminonitriles were hydrolysed and hydrogenolysed to lead for the first time to pure non-racemic (+)-1-amino-2-isopropylcyclobutanecarboxylic acid (ACBC) and its antipode. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00073-9

文献信息

• First synthesis of (1S,2S)- and (1R,2R)-1-amino-2-isopropylcyclobutanecarboxylic acids by asymmetric Strecker reaction from 2-substituted cyclobutanones
  作者：Molika Truong、Frédéric Lecornué、Antoine Fadel

  DOI：10.1016/s0957-4166(03)00073-9

  日期：2003.4

  An efficient and easy one-pot reaction from readily available racemic 2-substituted cyclobutanones gave, by means of asymmetric Strecker synthesis in the presence of an amine chiral auxiliary, two major aminonitriles with excellent diastereoselectivity. After separation, the major cis-aminonitriles were hydrolysed and hydrogenolysed to lead for the first time to pure non-racemic (+)-1-amino-2-isopropylcyclobutanecarboxylic acid (ACBC) and its antipode. (C) 2003 Elsevier Science Ltd. All rights reserved.