5,5-dimethyl-4-methylene-1,3,2-dioxathiolane-2-oxide

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: 5,5-dimethyl-4-methylene-1,3,2-dioxathiolane-2-oxide
• 英文别名: 4,4-Dimethyl-5-methylidene-1,3,2-dioxathiolane 2-oxide
• 化学式: C₅H₈O₃S
• 分子量: 148.183
• InChiKey: GSCIQJARHOUFNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-羟基-3-甲基-2-丁酮 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以58%的产率得到5,5-dimethyl-4-methylene-1,3,2-dioxathiolane-2-oxide
  参考文献：
  名称：

  Synthesis of 1,3,2-dioxathiolane-4-methylene-2-oxides: Potential allene oxide equivalents

  摘要：

  Two complementary approaches to 1,3,2-dioxathiolane-4-methylene-2-oxides are described. For example, treatment of 2-hydroxy-2-methylbutan-3-one with thionyl chloride (Et3N, CH2Cl2, -78 degrees C) yields 5,5-dimethyl-1,3,2-dioxathiolane-4-methylene-2-oxide 5 in 58% yield. Alternatively, cyclic sulfite 11, bearing a 4-(2-nitrophenylseleno)methyl substituent. can be induced to undergo oxidative elimination (30% H2O2, THF then CDCl3,Delta) to 5 in 28% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00598-0

文献信息

• Synthesis of 1,3,2-dioxathiolane-4-methylene-2-oxides: Potential allene oxide equivalents
  作者：Michael Shipman、Heidi R Thorpe、Ian R Clemens

  DOI：10.1016/s0040-4020(99)00598-0

  日期：1999.8

  Two complementary approaches to 1,3,2-dioxathiolane-4-methylene-2-oxides are described. For example, treatment of 2-hydroxy-2-methylbutan-3-one with thionyl chloride (Et3N, CH2Cl2, -78 degrees C) yields 5,5-dimethyl-1,3,2-dioxathiolane-4-methylene-2-oxide 5 in 58% yield. Alternatively, cyclic sulfite 11, bearing a 4-(2-nitrophenylseleno)methyl substituent. can be induced to undergo oxidative elimination (30% H2O2, THF then CDCl3,Delta) to 5 in 28% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.