tert-butyl-[(E,2R)-2-methylhex-3-en-5-ynoxy]-diphenylsilane | 521950-52-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl-[(E,2R)-2-methylhex-3-en-5-ynoxy]-diphenylsilane
• CAS: 521950-52-7
• 化学式: C₂₃H₂₈OSi
• 分子量: 348.56
• InChiKey: ZKSXZHLBWFCKJI-CDXDBMBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(E,2R)-2-methylhex-3-en-5-ynoxy]-diphenylsilane 在 5percent Pd(OAc)2 作用下， 以 乙醚 为溶剂， 生成 [(E,2R)-4-[(1R,2S,3S)-2-[(4R,5R)-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolan-2-yl]-3-methylcyclopropyl]-2-methylbut-3-enoxy]-tert-butyl-diphenylsilane
  参考文献：
  名称：

  Remarkable Stereocontrol in the Palladium-Catalysed Cyclopropanation of Vinyl- and Dienylboronates by Substituted Diazoalkanes

  摘要：

  Substituted diazoalkanes react smoothly, in the presence of catalytic amounts of Pd(OAc)(2), with a range of vinyl- and dienylboronates, affording in good to excellent yields, the corresponding trisubstituted cyclopropanes. The reaction is remarkably regio-, chemo-, and diastereoselective. The synthetic utility of this novel protocol is illustrated by the efficient assembly of the middle fragment of ambruticin.

  DOI：

  10.1002/1615-4169(200212)344:10<1063::aid-adsc1063>3.0.co;2-l
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl-[(E,2R)-2-methylhex-3-en-5-ynoxy]-diphenylsilane
  参考文献：
  名称：

  Regio- and stereoselective cyclopropanation of functionalised dienes. Novel methodology for the synthesis of vinyl- and divinyl-cyclopropanes

  摘要：

  Dienes, bearing an electron-withdrawing substituent at C-1, are cyclopropanated regio- and stereo selectively at the C-C double bond proximal to this electron-withdrawing group. The highest selectivity is observed in the case of dienylboronates. The cyclopropanation of these substrates affords almost exclusively the synthetically useful 1-boronato-2-vinyl-cyclopropanes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00242-3