(1R,2S)-2-羟基环己烷甲酰肼 | 217311-57-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,2S)-2-羟基环己烷甲酰肼
• 中文别名: 1-甲基-4-哌啶基2-[[7-(三氟甲基)喹啉-4-基]氨基]苯酸酯
• 英文名称: (1R,2S)-2-hydroxycyclohexane-1-carbohydrazide
• CAS: 217311-57-4
• 化学式: C₇H₁₄N₂O₂
• 分子量: 158.2
• InChiKey: JEQMQBRLQLBAEY-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-羟基环己烷甲酰肼 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.0h， 以89%的产率得到cis-hexahydrobenzoxazol-2-one
  参考文献：
  名称：

  A novel highly stereoselective synthesis of chiral 5- and 4,5-substituted 2-oxazolidinones

  摘要：

  A novel highly stereoselective synthesis of chiral mono- and bicyclic 4- and 4,5-substituted 2-oxazolidinones starting from P-keto esters was developed. After bioreduction with S. cerevisiae the resulting homochiral P-hydroxy esters are transformed into their hydrazides. Treatment with NaNO2/H+ then furnishes 2-oxazolidinones in high e.e. (similar to 99%) and d.e. (> 99%). The ring formation proceeds via a highly concerted sextet rearrangement with full retention of configuration at the stereocentres. Enantiopure 1,2-amino alcohols can subsequently be obtained by saponification of the 2-oxazolidinone products. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00364-0
• 作为产物：
  描述：

  (1R,2S)-2-羟基-环己烷羧酸乙酯 在 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以97%的产率得到(1R,2S)-2-羟基环己烷甲酰肼
  参考文献：
  名称：

  A novel highly stereoselective synthesis of chiral 5- and 4,5-substituted 2-oxazolidinones

  摘要：

  A novel highly stereoselective synthesis of chiral mono- and bicyclic 4- and 4,5-substituted 2-oxazolidinones starting from P-keto esters was developed. After bioreduction with S. cerevisiae the resulting homochiral P-hydroxy esters are transformed into their hydrazides. Treatment with NaNO2/H+ then furnishes 2-oxazolidinones in high e.e. (similar to 99%) and d.e. (> 99%). The ring formation proceeds via a highly concerted sextet rearrangement with full retention of configuration at the stereocentres. Enantiopure 1,2-amino alcohols can subsequently be obtained by saponification of the 2-oxazolidinone products. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00364-0

文献信息

• FULOP, FERENC;SEMEGA, EVA;DOMBI, GYORGY;BERNATH, GABOR, J. HETEROCYCL. CHEM., 27,(1990) N, C. 951-955
  作者：FULOP, FERENC、SEMEGA, EVA、DOMBI, GYORGY、BERNATH, GABOR

  DOI：——

  日期：——