(4'S,Z)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-ylmethylene)tetrahydrofuran-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4'S,Z)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-ylmethylene)tetrahydrofuran-2-one
• 英文别名: (3Z)-3-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylidene]oxolan-2-one
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: XGUUHNVDUCPMCH-TVSKSKRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  碘环己烷 、 (4'S,Z)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-ylmethylene)tetrahydrofuran-2-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 (1'S,4''S)-3-<1'-cyclohexyl-1'-(2'',2''-dimethyl-1'',3''-dioxolan-4''-yl)methyl>tetrahydrofuran-2-one 、 (3S,1'R,4''S)-3-<1'-cyclohexyl-1'-(2'',2''-dimethyl-1'',3''-dioxolan-4''-yl)methyl>tetrahydrofuran-2-one 、 (3R,1'R,4''S)-3-<1'-cyclohexyl-1'-(2'',2''-dimethyl-1'',3''-dioxolan-4''-yl)methyl>tetrahydrofuran-2-one
  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：

  γ-丁内酯 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium diisopropyl amide 作用下， 生成 (4'S,Z)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-ylmethylene)tetrahydrofuran-2-one 、 (4'S,E)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-ylmethylene)tetrahydrofuran-2-one
  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

文献信息

• Stereoselective radical additions of γ-oxy-α,β-unsaturated ester derivatives; 1,2-asymmetric induction in acyclic and cyclisation systems
  作者：Tsutomu Morikawa、Yoshiaki Washio、Susumu Harada、Ryo Hanai、Takashi Kayashita、Hisako Nemoto、Motoo Shiro、Takeo Taguchi

  DOI：10.1039/p19950000271

  日期：——

  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.