methyl (3E,2R,5R)-5-tert-butyldimethylsiloxy-2-vinyl-3-hexenoate | 155068-52-3

• 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: methyl (3E,2R,5R)-5-tert-butyldimethylsiloxy-2-vinyl-3-hexenoate
• 英文别名: methyl (E,2R,5R)-5-[tert-butyl(dimethyl)silyl]oxy-2-ethenylhex-3-enoate
• CAS: 155068-52-3
• 化学式: C₁₅H₂₈O₃Si
• 分子量: 284.471
• InChiKey: MGUGQKCXADDPIF-HRFIDBLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (3E,2R,5R)-5-tert-butyldimethylsiloxy-2-vinyl-3-hexenoate 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (3E,2R,5R)-1-benzyloxy-5-(tert-butyldimethyl)siloxy-2-vinyl-3-hexene
  参考文献：
  名称：

  Remarkable difference in reactivity of ordinary vinylcopper reagents and vinylzinc halide containing a copper salt towards γ-mesyloxy-α, β-enoates. Synthesis of homochiral 1,4-dienes

  摘要：

  Whereas the reaction of gamma-mesyloxy alpha,beta-enoates with vinyl-Cu(CN)M or (vinyl)2Cu(CN)M2 (M = Li or MgX) yielded a reduction product with an (E)-double bond at the beta,gamma-position, treatment of the same substrates with ''higher order'' zinc cuprate reagents or vinyl-ZnCl by the addition of catalytic amount of Cu(I) or Cu(II) salt afforded alpha- and gamma-vinylation products. Both vinylation products were stable 1,4-diene derivatives that are only more difficulty accessed by more traditional means.

  DOI：

  10.1016/s0040-4020(01)80217-9
• 作为产物：
  描述：

  乙烯基氯化镁 、 methyl (Z,4S,5R)-4-mesyloxy-5-(tert-butyldimethyl)siloxy-2-hexenoate 在 lithium chloride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 5.0h， 以67%的产率得到methyl (3E,2R,5R)-5-tert-butyldimethylsiloxy-2-vinyl-3-hexenoate
  参考文献：
  名称：

  Remarkable difference in reactivity of ordinary vinylcopper reagents and vinylzinc halide containing a copper salt towards γ-mesyloxy-α, β-enoates. Synthesis of homochiral 1,4-dienes

  摘要：

  Whereas the reaction of gamma-mesyloxy alpha,beta-enoates with vinyl-Cu(CN)M or (vinyl)2Cu(CN)M2 (M = Li or MgX) yielded a reduction product with an (E)-double bond at the beta,gamma-position, treatment of the same substrates with ''higher order'' zinc cuprate reagents or vinyl-ZnCl by the addition of catalytic amount of Cu(I) or Cu(II) salt afforded alpha- and gamma-vinylation products. Both vinylation products were stable 1,4-diene derivatives that are only more difficulty accessed by more traditional means.

  DOI：

  10.1016/s0040-4020(01)80217-9

文献信息

• Remarkable difference in reactivity of ordinary vinylcopper reagents and vinylzinc halide containing a copper salt towards γ-mesyloxy-α, β-enoates. Synthesis of homochiral 1,4-dienes
  作者：Toshiro Ibuka、Kazuo Nakai、Hiromu Habashita、Kiyoshi Bessho、Nobutaka Fujii、Yukiyasu Chounan、Yoshinori Yamamoto

  DOI：10.1016/s0040-4020(01)80217-9

  日期：——

  Whereas the reaction of gamma-mesyloxy alpha,beta-enoates with vinyl-Cu(CN)M or (vinyl)2Cu(CN)M2 (M = Li or MgX) yielded a reduction product with an (E)-double bond at the beta,gamma-position, treatment of the same substrates with ''higher order'' zinc cuprate reagents or vinyl-ZnCl by the addition of catalytic amount of Cu(I) or Cu(II) salt afforded alpha- and gamma-vinylation products. Both vinylation products were stable 1,4-diene derivatives that are only more difficulty accessed by more traditional means.