3-(4-chlorophenyl)-2-<(trimethylsilyl)ethynyl>oxirane | 143798-88-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-chlorophenyl)-2-<(trimethylsilyl)ethynyl>oxirane
• 英文别名: 1-(p-chlorophenyl)-2-trimethylsilylethynyl epoxide；2-[(2S,3R)-3-(4-chlorophenyl)oxiran-2-yl]ethynyl-trimethylsilane
• CAS: 143798-88-3；143798-97-4
• 化学式: C₁₃H₁₅ClOSi
• 分子量: 250.8
• InChiKey: WWUBDBCPEBJRMG-QWHCGFSZSA-N

物化性质

• 沸点：
  299.3±40.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-溴-1-三甲基硅基-1-丙炔 在 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 反应 4.0h， 生成 3-(4-chlorophenyl)-2-<(trimethylsilyl)ethynyl>oxirane
  参考文献：
  名称：

  Application of elementoorganic compounds of 15th and 16th Groups in organic synthesis. 100. Reactions of carbonyl compounds with [(trimethylsilyl)propargyl]diisobutyltelluronium bromide mediated by different strong bases: highly regioselective synthesis of (trimethylsilyl)propargyl alcohols and highly stereoselective synthesis of cis-(trimethylsilyl)alkynyl epoxides

  摘要：

  [(Trimethylsilyl)propargyl)]diisobutyltelluronium bromide (1), after being treated with alkyl- or aryllithium reagent, undergoes a lithium-tellurium exchange reaction via an unstable transient tetraorganyltellurium intermediate, and the in situ generated lithium species reacts with carbonyl compounds to give (trimethylsilyl)propargyl alcohols 2 in high yields with high regioselectivity. However, when the telluronium salt 1 was treated with nonnucleophilic bases such as LDA or lithium 2,2,6,6-tetramethylpiperidide, the moderately stabilized silylated telluronium ylide formed. The silylated telluronium ylide reacted with carbonyl compounds to afford (trimethylsilyl) alkynyl epoxides 11 in good to excellent yields with high cis stereoselectivity.

  DOI：

  10.1021/jo00050a042

文献信息

• Facile and highly stereoselective synthesis of cis-trimethylsilylethynyl epoxides via a silylated telluronium ylide
  作者：Zhang-Lin Zhou、Yao-Zeng Huang、Li-Lan Shi

  DOI：10.1039/c39920000986

  日期：——

  Diisobutyltelluronium trimethylsilylpropynyl ylide, generated from 3-trimethylsilylprop-2-ynyldiisobutyltelluronium bromide with lithium 2,2,6,6-tetramethylpiperidide (LiTMP), reacts with carbonyl compounds to afford predominately cis-trimethylsilylethynyl epoxides in good to excellent yields.

  由3-三甲基甲硅烷基丙-2-炔基二异丁基碲化溴化锂与2,2,6,6-四甲基哌啶锂（LiTMP）生成的二异丁基碲铝三甲基甲硅烷基丙炔基内酯与羰基化合物反应生成主要为顺式-三甲基甲硅烷基乙炔基环氧化物，收率良好。