Benzoic acid (7E,9E)-10-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-deca-7,9-dienyl ester | 439812-33-6

• 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: Benzoic acid (7E,9E)-10-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-deca-7,9-dienyl ester
• 英文别名: [(7E,9E)-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)deca-7,9-dienyl] benzoate
• CAS: 439812-33-6
• 化学式: C₂₃H₃₃BO₄
• 分子量: 384.324
• InChiKey: YGFPHJAAIZQIFA-QSJOIONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 Benzoic acid (7E,9E)-10-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-deca-7,9-dienyl ester 在 palladium diacetate 作用下， 以 乙醚 为溶剂， 以65%的产率得到Benzoic acid (E)-8-[(1R,2R)-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-cyclopropyl]-oct-7-enyl ester
  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：

  Benzoic acid (E)-10-trimethylsilanyl-dec-7-en-9-ynyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 Benzoic acid (7E,9E)-10-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-deca-7,9-dienyl ester
  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