(Z)-(1R,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-2-trimethylsilyl-hept-2-en-1-ol | 102357-27-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-(1R,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-2-trimethylsilyl-hept-2-en-1-ol
• 英文别名: (Z,1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trimethylsilylhept-2-en-1-ol
• CAS: 102357-27-7
• 化学式: C₁₅H₃₀O₃Si
• 分子量: 286.487
• InChiKey: AKDJBAUWQKFHEV-NKMUALHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-(1R,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-2-trimethylsilyl-hept-2-en-1-ol 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以28%的产率得到(E)-(1R,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-2-trimethylsilylhept-2-en-1-ol
  参考文献：
  名称：

  Diastereoselective addition of lower order vinylcuprates to (R)-2,3-O-Isopropylideneglyceraldehyde

  摘要：

  Highly syn or anti selective addition of lower order lithium vinylcuprates generated from alkenyl bromides 1 to (R)-2,3-O-isopropylideneglyceraldehyde (2) can be achieved, respectively, depending on the substitution pattern of the vinyl moiety and the solvent. Alpha-Trimethylsilyl substituted vinylcuprates possessing an alkyl substituent Z to copper react with excellent syn selectivity in ether whereas a highly anti selective addition is observed for cuprates bearing a hydrogen atom Z or alpha to the metal in THF. A model is proposed to rationalize these complementary selectivities.

  DOI：

  10.1016/s0040-4020(01)81551-9
• 作为产物：
  描述：

  2,2-二甲基-1,3-二氧戊环-4-甲醛 生成 (Z)-(1R,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-2-trimethylsilyl-hept-2-en-1-ol
  参考文献：
  名称：

  CATO, FUMIEH

  摘要：

  DOI：

文献信息

• On the palladium(II)-catalyzed rearrangement of allyl imidates
  作者：Peter Metz、Cornelia Mues、Andreas Schoop

  DOI：10.1016/s0040-4020(01)88203-x

  日期：1992.1

  Polyhetero-[3,3]-sigmatropic rearrangements of allyl N-phenylimidates 4a - ▾ catalyzed by dichlorobis- (benzonitrile)palladium(II) are shown to afford N-allyl-N-phenylamides in good to excellent yields for substitution patterns that have so far precluded cyclization-induced allyl shifts. Using trichloroacetimidates of secondary allyl alcohols as substrates, the palladium(II)-catalyst effects a completely (E)

  由二氯双-（苄腈）钯（II）催化的N-苯基亚氨酸甲酯烯丙基4a-▾的多- [3,3]-σ重排表明，N-烯丙基-N-苯基酰胺具有良好的收率，可以很好地取代具有迄今为止，还没有排除环化引起的烯丙基转移。使用仲烯丙醇的三氯乙酰亚胺酸酯作为底物，钯（II）催化剂在室温下实现完全（E）立体选择性重排，并进行完全手性转移。该反应已经应用于从（R）-2，3-0-异亚丙基甘油醛氢化物（17）开始的（R）-N-（三氯乙酰基）降冰片酚（18）的合成。
• Synthesis of optically active .beta.,.gamma.-epoxy alcohols and secondary allylic alcohols via diastereoselective addition of .alpha.-(trimethylsilyl)-.alpha.,.beta.-epoxy aldehydes with organometallic compounds
  作者：Yoshiyuki Takeda、Takashi Matsumoto、Fumie Sato

  DOI：10.1021/jo00374a047

  日期：1986.11
• CATO, FUMIEH
  作者：CATO, FUMIEH

  DOI：——

  日期：——
• Diastereoselective addition of lower order vinylcuprates to (R)-2,3-O-Isopropylideneglyceraldehyde
  作者：Peter Metz、Andreas Schoop

  DOI：10.1016/s0040-4020(01)81551-9

  日期：1993.1

  Highly syn or anti selective addition of lower order lithium vinylcuprates generated from alkenyl bromides 1 to (R)-2,3-O-isopropylideneglyceraldehyde (2) can be achieved, respectively, depending on the substitution pattern of the vinyl moiety and the solvent. Alpha-Trimethylsilyl substituted vinylcuprates possessing an alkyl substituent Z to copper react with excellent syn selectivity in ether whereas a highly anti selective addition is observed for cuprates bearing a hydrogen atom Z or alpha to the metal in THF. A model is proposed to rationalize these complementary selectivities.