(E)-(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-ethyl-hex-3-enoic acid methyl ester | 121011-99-2

• 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: (E)-(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-ethyl-hex-3-enoic acid methyl ester
• CAS: 121011-99-2
• 化学式: C₁₅H₃₀O₃Si
• 分子量: 286.487
• InChiKey: KASSMUHXVNFAFT-HRFIDBLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-ethyl-hex-3-enoic acid methyl ester 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 2.0h， 生成 (3E,2R,5R)-1-benzyloxy-5-(tert-butyldimethyl)siloxy-2-ethyl-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：

  乙基锂 、 methyl (E,4R,5R)-4-mesyloxy-5-(tert-butyldimethyl)siloxy-2-hexenoate 在 三氟化硼乙醚 作用下， 生成 (E)-(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-ethyl-hex-3-enoic acid methyl ester
  参考文献：
  名称：

  Very high chemoselective, regioselective, and E-stereoselective 1,3-chirality transfer involving reaction of acyclic (E)- and (Z)-.gamma.-mesyloxy .alpha.,.beta.-enoates and organocyanocopper-trifluoroborane reagents. Efficient synthetic routes to functionalized chiral .alpha.-alkyl (E)-.beta.,.gamma.-enoates and (E)-allylic alcohols with high optical purity

  摘要：

  DOI：

  10.1021/ja00195a045