chloralide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: chloralide
• 英文别名: trans-2,5-bis(trichloromethyl)-1,3-dioxolan-4-one；trans-chloralide；(+/-)-trans-2,5-Bis-trichlormethyl-[1,3]dioxolan-4-on；(2R,5R)-2,5-bis(trichloromethyl)-1,3-dioxolan-4-one
• 化学式: C₅H₂Cl₆O₃
• 分子量: 322.787
• InChiKey: MURYNVIRLILSCR-NPKIIWCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  水合氯醛 、 一氧化碳 在 硫酸 作用下， 47.0 ℃ 、5.07 MPa 条件下， 反应 7.0h， 以14.6%的产率得到3,3,3-三氯乳酸
  参考文献：
  名称：

  Carbonylation of trichloroacetaldehyde (chloral) in concentrated sulfuric acid: Stereocontrolled synthesis of cis- and trans-2,5-bis(trichloromethyl)-1,3-dioxolan-4-one

  摘要：

  Carbonylation of trichloroacetaldehyde(chloral) in concentrated sulfuric acid readily gave 2,5-bis(trichloromethyl)-1,3-dioxolan-4-ones (cis and trans) and 3,3,3-trichloro-2-hydroxypropanoic acid. The cis isomer was isolated for the first time, and confirmed by Xray structural analysis. The cis/trans ratio of dioxolanones largely depended upon the concentration of sulfuric acid. Highly diastereoselective formation of the dioxolanones was achieved with 99wt% sulfuric acid (cis : trans = 95 : 5) or with 90wt% sulfuric acid (0 : 100).

  DOI：

  10.1016/0040-4020(95)00516-b

文献信息

• Carbonylation of trichloroacetaldehyde (chloral) in concentrated sulfuric acid: Stereocontrolled synthesis of cis- and trans-2,5-bis(trichloromethyl)-1,3-dioxolan-4-one
  作者：Sadayuki Mori、Kazuhiro Emura、Motoaki Kano、Kiyoshi Kudo、Koichi Komatsu、Nobuyuki Sugita

  DOI：10.1016/0040-4020(95)00516-b

  日期：1995.8

  Carbonylation of trichloroacetaldehyde(chloral) in concentrated sulfuric acid readily gave 2,5-bis(trichloromethyl)-1,3-dioxolan-4-ones (cis and trans) and 3,3,3-trichloro-2-hydroxypropanoic acid. The cis isomer was isolated for the first time, and confirmed by Xray structural analysis. The cis/trans ratio of dioxolanones largely depended upon the concentration of sulfuric acid. Highly diastereoselective formation of the dioxolanones was achieved with 99wt% sulfuric acid (cis : trans = 95 : 5) or with 90wt% sulfuric acid (0 : 100).