ethyl (4'S,Z)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-(4-iodobutyl)prop-2-enoate | 162333-96-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (4'S,Z)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-(4-iodobutyl)prop-2-enoate
• 英文别名: ethyl (2Z)-2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylidene]-6-iodohexanoate
• CAS: 162333-96-2
• 化学式: C₁₄H₂₃IO₄
• 分子量: 382.239
• InChiKey: KMPGRTDXUGNCRF-MMRAYRKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (4'S,Z)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-(4-iodobutyl)prop-2-enoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 ethyl (4'S)-1-(2',2'-dimethyl-1',3'-dioxolan-4'ylmethyl)cyclopentanecarboxylate 、 ethyl (1S,2R,4'S)-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclohexanecarboxylate 、 ethyl (1R,2R,4'S)-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclohexanecarboxylate 、 ethyl (1S,2S,4'S)-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclohexanecarboxylate
  参考文献：
  名称：

  Stereoselective radical additions of γ-oxy-α,β-unsaturated ester derivatives; 1,2-asymmetric induction in acyclic and cyclisation systems

  摘要：

  Examination was made of 1,2-asymmetric induction in the addition of alkyl radicals to gamma-oxy-alpha,beta-unsaturated ester derivatives 1 and 2 prepared from ethyl lactate and (R)-2,3-0-isopropylideneglyceraldehyde 3, respectively. The addition reactions of hexyl, cyclohexyl and 3-phenylpropyl radicals to (Z)-2 derived from aldehyde 3 gave beta-addition products with syn-stereoselectivity (syn:anti = 8.6:1-syn only). The reactions of (E)-2 were non-stereoselective. Based on allylic strain, a transition-state model for the syn-stereoselectivity is proposed. 1,2-Asymmetric induction was carried out in radical cyclisation to synthesize optically active cyclohexane derivatives.

  DOI：

  10.1039/p19950000271
• 作为产物：
  描述：

  ethyl 6-((tert-butyldimethylsilyl)oxy)hexanoate 在 四丁基氟化铵 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 sodium iodide 、 lithium diisopropyl amide 作用下， 生成 ethyl (4'S,Z)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-(4-iodobutyl)prop-2-enoate
  参考文献：
  名称：

  Stereoselective radical additions of γ-oxy-α,β-unsaturated ester derivatives; 1,2-asymmetric induction in acyclic and cyclisation systems

  摘要：

  Examination was made of 1,2-asymmetric induction in the addition of alkyl radicals to gamma-oxy-alpha,beta-unsaturated ester derivatives 1 and 2 prepared from ethyl lactate and (R)-2,3-0-isopropylideneglyceraldehyde 3, respectively. The addition reactions of hexyl, cyclohexyl and 3-phenylpropyl radicals to (Z)-2 derived from aldehyde 3 gave beta-addition products with syn-stereoselectivity (syn:anti = 8.6:1-syn only). The reactions of (E)-2 were non-stereoselective. Based on allylic strain, a transition-state model for the syn-stereoselectivity is proposed. 1,2-Asymmetric induction was carried out in radical cyclisation to synthesize optically active cyclohexane derivatives.

  DOI：

  10.1039/p19950000271