(+/-)-cis-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-(valeryloxymethyl)-1,3-dioxolane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-cis-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-(valeryloxymethyl)-1,3-dioxolane
• 英文别名: [(2S,4S)-2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methyl pentanoate
• 化学式: C₁₆H₁₉BrCl₂O₄
• 分子量: 426.134
• InChiKey: UQTIRAFUROYETN-MLGOLLRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-cis-[2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-yl]methyl benzoate 在 4-二甲氨基吡啶 、 氢氧化钾 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (+/-)-cis-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-(valeryloxymethyl)-1,3-dioxolane
  参考文献：
  名称：

  Lipase-catalyzed resolution of 1,3-dioxolane derivatives: synthesis of a homochiral intermediate for antifungal agents

  摘要：

  Dioxolane alcohol (+/-)-1 and the corresponding acid (+/-)-2 were kinetically resolved into their respective enantiomers by lipase-catalyzed hydrolysis and esterification reactions. Various alcohols were tested to resolve the acid (+/-)-2, and the desired (2R,4R)-isomer of the acid was obtained with >96% ee as the best result. Halogenated solvents such as methylene chloride and 1,2-dichloroethane were found to raise the reactivity and selectivity of the system. After recrystallization, the purity of the desired (2R,4R)-acid could be increased to over 98% ee. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00662-6