(Z)-1-(trimethylsilyl)oct-1-en-4-ol | 1342304-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-(trimethylsilyl)oct-1-en-4-ol
• 英文别名: (Z)-1-trimethylsilyloct-1-en-4-ol
• CAS: 1342304-60-2
• 化学式: C₁₁H₂₄OSi
• 分子量: 200.396
• InChiKey: KSEOGZYZJTUDBL-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲基环氧丙烷 、 (Z)-1-(trimethylsilyl)oct-1-en-4-ol 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到cis-2-butyl-6-isopropyl-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Bi(OTf)₃-, TfOH-, and TMSOTf-Mediated, One-Pot Epoxide Rearrangement, Addition, and Intramolecular Silyl-Modified Sakurai (ISMS) Cascade toward Dihydropyrans: Comparison of Catalysts and Role of Bi(OTf)₃

  摘要：

  Catalytic quantities of bismuth(III) triflate efficiently initiate the rearrangement of epoxides to aldehydes, which subsequently react with (Z)-delta-hydroxyalkenylsilanes to afford 2,6-disubstituted 3,6-dihydro-2H-pyrans. Isolated yields of desired products using Bi(OTf)(3) were compared with yields obtained when the reactions were run with TfOH and TMSOTf in the presence and absence of several additives. These studies, as well as NMR spectroscopic analyses, indicate an initial Lewis acid/base interaction between Bi(OTf)(3) and substrates providing TfOH in situ.

  DOI：

  10.1021/jo201478d

文献信息

• Bi(OTf)₃-, TfOH-, and TMSOTf-Mediated, One-Pot Epoxide Rearrangement, Addition, and Intramolecular Silyl-Modified Sakurai (ISMS) Cascade toward Dihydropyrans: Comparison of Catalysts and Role of Bi(OTf)₃
  作者：R. Frederick Lambert、Robert J. Hinkle、Stephen E. Ammann、Yajing Lian、Jia Liu、Shane E. Lewis、Robert D. Pike

  DOI：10.1021/jo201478d

  日期：2011.11.18

  Catalytic quantities of bismuth(III) triflate efficiently initiate the rearrangement of epoxides to aldehydes, which subsequently react with (Z)-delta-hydroxyalkenylsilanes to afford 2,6-disubstituted 3,6-dihydro-2H-pyrans. Isolated yields of desired products using Bi(OTf)(3) were compared with yields obtained when the reactions were run with TfOH and TMSOTf in the presence and absence of several additives. These studies, as well as NMR spectroscopic analyses, indicate an initial Lewis acid/base interaction between Bi(OTf)(3) and substrates providing TfOH in situ.