4,4,5,5-tetramethyl-2-[(1E,3E)-6-phenylhexa-1,3-dienyl]-1,3,2-dioxaborolane | 439812-32-5

• 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: 4,4,5,5-tetramethyl-2-[(1E,3E)-6-phenylhexa-1,3-dienyl]-1,3,2-dioxaborolane
• CAS: 439812-32-5
• 化学式: C₁₈H₂₅BO₂
• 分子量: 284.206
• InChiKey: ADMUGJZMLXJJNH-GCXOIEGYSA-N

物化性质

• 沸点：
  355.8±45.0 °C(predicted)
• 密度：
  0.98±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 4,4,5,5-tetramethyl-2-[(1E,3E)-6-phenylhexa-1,3-dienyl]-1,3,2-dioxaborolane 在 palladium diacetate 作用下， 以 乙醚 为溶剂， 以66%的产率得到4,4,5,5-tetramethyl-2-[(1R,2R)-2-[(E)-4-phenylbut-1-enyl]cyclopropyl]-1,3,2-dioxaborolane
  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
• 作为产物：
  描述：

  trans-6-phenyl-1-trimethylsilylhex-3-en-1-yne 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 4,4,5,5-tetramethyl-2-[(1E,3E)-6-phenylhexa-1,3-dienyl]-1,3,2-dioxaborolane
  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

文献信息

• Remarkable Stereocontrol in the Palladium-Catalysed Cyclopropanation of Vinyl- and Dienylboronates by Substituted Diazoalkanes
  作者：István E Markó、Takuya Kumamoto、Thierry Giard

  DOI：10.1002/1615-4169(200212)344:10<1063::aid-adsc1063>3.0.co;2-l

  日期：2002.12

  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.