2-[(1E,3E,11Z)-icosa-1,3,11-trienyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 439812-35-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 2-[(1E,3E,11Z)-icosa-1,3,11-trienyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 439812-35-8
• 化学式: C₂₆H₄₇BO₂
• 分子量: 402.469
• InChiKey: BNXBRQSNKCGRDT-RBIRMMIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.38
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 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 、 2-[(1E,3E,11Z)-icosa-1,3,11-trienyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 palladium diacetate 作用下， 以 乙醚 为溶剂， 以63%的产率得到
  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：

  heptadec-8c-enal 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 2-[(1E,3E,11Z)-icosa-1,3,11-trienyl]-4,4,5,5-tetramethyl-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

• Regio- and stereoselective cyclopropanation of functionalised dienes. Novel methodology for the synthesis of vinyl- and divinyl-cyclopropanes
  作者：István E. Markó、Thierry Giard、Shinichi Sumida、Anne-Elisabeth Gies

  DOI：10.1016/s0040-4039(02)00242-3

  日期：2002.3

  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.