(1R,2S)-2-羟基环戊烷甲酰肼 | 216879-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,2S)-2-羟基环戊烷甲酰肼
• 英文名称: (1R,2S)-2-Hydroxycyclopentane-1-carbohydrazide
• CAS: 216879-03-7
• 化学式: C₆H₁₂N₂O₂
• 分子量: 144.173
• InChiKey: WJADOCJMCWWZQH-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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-羟基环戊烷甲酰肼 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.0h， 以88%的产率得到cis-hexahydrocyclopentaoxazol-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：

  ethyl (1R,2S)-2-hydroxycyclopentanecarboxylate 在 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以96%的产率得到(1R,2S)-2-羟基环戊烷甲酰肼
  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：——
• US5942644A
  申请人：——

  公开号：US5942644A

  公开（公告）日：1999-08-24
• A novel highly stereoselective synthesis of chiral 5- and 4,5-substituted 2-oxazolidinones
  作者：M Bertau、M Bürli、E Hungerbühler、P Wagner

  DOI：10.1016/s0957-4166(01)00364-0

  日期：2001.8

  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.