4(S)-(-)-((E)-4-hydroxy-pent-1-en-1-yl)boronic acid | 216772-56-4

• 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: 4(S)-(-)-((E)-4-hydroxy-pent-1-en-1-yl)boronic acid
• 英文别名: [(E,4S)-4-hydroxypent-1-enyl]boronic acid
• CAS: 216772-56-4
• 化学式: C₅H₁₁BO₃
• 分子量: 129.952
• InChiKey: CDAZEWNVUBJOSL-FYTLMZHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.67
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4(S)-(-)-((E)-4-hydroxy-pent-1-en-1-yl)boronic acid 、 3-[(1E,6E)-7-iodohepta-1,6-dienyl]pyridine 在 四(三苯基膦)钯 、 氢氧化铊(Ⅰ) 作用下， 生成 (+)-haminol A
  参考文献：
  名称：

  Synthesis of haminol-A and haminol-B, polyenic alarm pheromones of Cephalaspidean molluscs

  摘要：

  Two stereocontrolled palladium-catalyzed cross-couplings of I-alkenyl boronic acids and aryl/alkenyl halides (the Suzuki-Miyaura reaction) are the key steps in an enantioselective approach to the polyene fragment of haminols A and B, alarm pheromones isolated from Haminoea navicula, a Cephalaspidean Opisthobranch mollusc. Chirality rested on the use of (S)-propylene oxide as the starting material. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00324-3

文献信息

• Synthesis of haminol-A and haminol-B, polyenic alarm pheromones of Cephalaspidean molluscs
  作者：Rosana Alvarez、Angel R. de Lera

  DOI：10.1016/s0957-4166(98)00324-3

  日期：1998.9

  Two stereocontrolled palladium-catalyzed cross-couplings of I-alkenyl boronic acids and aryl/alkenyl halides (the Suzuki-Miyaura reaction) are the key steps in an enantioselective approach to the polyene fragment of haminols A and B, alarm pheromones isolated from Haminoea navicula, a Cephalaspidean Opisthobranch mollusc. Chirality rested on the use of (S)-propylene oxide as the starting material. (C) 1998 Elsevier Science Ltd. All rights reserved.