trans-3,5-bis-(chloromethyl)-3,5-dimethoxy-1,2,4-trioxolane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三氧戊环
• 英文名称: trans-3,5-bis-(chloromethyl)-3,5-dimethoxy-1,2,4-trioxolane
• 英文别名: trans-3,5-Bis(chloromethyl)-3,5-dimethoxy-trioxolane；(3S,5S)-3,5-bis(chloromethyl)-3,5-dimethoxy-1,2,4-trioxolane
• 化学式: C₆H₁₀Cl₂O₅
• 分子量: 233.048
• InChiKey: SYFWRZPULBWHSI-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trans-3,5-bis-(chloromethyl)-3,5-dimethoxy-1,2,4-trioxolane 在 盐酸 作用下， 以 氘代氯仿 为溶剂， 反应 24.0h， 以72%的产率得到氯乙酸甲酯
  参考文献：
  名称：

  Nucleophilic Substitution Reactions at Chloro-Substituted Ozonides and at a Chlorinated Dimeric Peroxide

  摘要：

  Reactions of substituted 3-chloro-(2a-4a) and 3,5-dichloro-1,2,4-trioxolanes (9a, 10a) with AgBF4 in the presence of LiF gave the corresponding fluoro-substituted ozonides (2b-4b and 9b and 10b). Substitutions af some of these chlorinated ozonides by the methoxy and by the acetoxy groups, and of 3,6-dichloro-3,6-dimethyl-1,2,4,5-tetrox (22a) with the acetoxy group have been achieved, too.

  DOI：

  10.1021/jo00129a055
• 作为产物：
  描述：

  甲醇 、 E-1,4-dichloro-2,3-dibromo-2-butene 在 silver tetrafluoroborate 、 臭氧 作用下， 生成 cis-3,5-bis-(chloromethyl)-3,5-dimethoxy-1,2,4-trioxolane 、 trans-3,5-bis-(chloromethyl)-3,5-dimethoxy-1,2,4-trioxolane
  参考文献：
  名称：

  Detection of Elusive Chloro- and Bromo Substituted Ozonides by nucleophilic substitution reactions

  摘要：

  Ozonolyses of 2,3-dichloro-2-butene (4), 4,5-dichloro-4-octene (9) and 2,3-dibromo-1,4-dichloro-2-butene (12) on polyethylene gave the corresponding ozonides 5, 10 and 13a, respectively, which could not be isolated or unequivocally identified. Their identity could be proven, however, via substitution of the chloro- or bromo substituents at the ozonide rings by stabilizing substituents and subsequent isolation of the substituted ozonides 6, 11, 13b and 13c. Ozonolysis of 2,3-diacetoxy-2-butene (14) on polyethylene, in dichloro methane and in pentane gave mixtures of 16 and 17 but not ozonide 6.

  DOI：

  10.1002/prac.19963380162