2-(1,3-dimethylhexa-1,3-dienyl)benzo[1,2,3]dioxaborole | 851677-10-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-(1,3-dimethylhexa-1,3-dienyl)benzo[1,2,3]dioxaborole
• 英文别名: 2-[(2Z,4E)-4-methylhepta-2,4-dien-2-yl]-1,3,2-benzodioxaborole
• CAS: 851677-10-6
• 化学式: C₁₄H₁₇BO₂
• 分子量: 228.099
• InChiKey: RCGCRNYWLBPABC-CRALUGIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2-((2E,4Z)-5-iodo-4-methylpenta-2,4-dien-2-yl)-6-methoxy-3,5-dimethyl-4H-pyran-4-one 、 2-(1,3-dimethylhexa-1,3-dienyl)benzo[1,2,3]dioxaborole 在 四(三苯基膦)钯 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-methoxy-3,5-dimethyl-6-((2E,4Z,6E,8E)-4,6,8-trimethylundeca-2,4,6,8-tetraen-2-yl)-4H-pyran-4-one
  参考文献：
  名称：

  （+/-）-9,10-脱氧三丁酮的仿生合成。

  摘要：

  串联的铃木-偶联/电环化反应序列用于（+/-）-9,10-脱氧三丁酮的仿生合成。

  DOI：

  10.1039/b418988d
• 作为产物：
  描述：

  2-甲基-2-戊烯醛 在 正丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(1,3-dimethylhexa-1,3-dienyl)benzo[1,2,3]dioxaborole
  参考文献：
  名称：

  Total synthesis of cyercene A and the biomimetic synthesis of (±)-9,10-deoxytridachione and (±)-ocellapyrone A

  摘要：

  This paper summarises our detailed study towards the biomimetic synthesis of the complex polypropionate derived natural product (+/-)-9,10-deoxytridachione. A previous study based on the elaboration of functionalised gamma-pyrones allowed us to synthesise cyercene A. The same efficient methodology has been applied for the elaboration of a more complex fully conjugated gamma-pyrone polyene. Our approach centred on a key tandem Suzuki-coupling/electrocyclisation reaction, which supports a possible biosynthetic pathway for this class of natural products. A related compound was obtained during our studies, which we identified as the correct structure of ocellapyrone A. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.03.057

文献信息

• Total synthesis of cyercene A and the biomimetic synthesis of (±)-9,10-deoxytridachione and (±)-ocellapyrone A
  作者：Raphaël Rodriguez、Robert M. Adlington、Serena J. Eade、Magnus W. Walter、Jack E. Baldwin、John E. Moses

  DOI：10.1016/j.tet.2007.03.057

  日期：2007.5

  This paper summarises our detailed study towards the biomimetic synthesis of the complex polypropionate derived natural product (+/-)-9,10-deoxytridachione. A previous study based on the elaboration of functionalised gamma-pyrones allowed us to synthesise cyercene A. The same efficient methodology has been applied for the elaboration of a more complex fully conjugated gamma-pyrone polyene. Our approach centred on a key tandem Suzuki-coupling/electrocyclisation reaction, which supports a possible biosynthetic pathway for this class of natural products. A related compound was obtained during our studies, which we identified as the correct structure of ocellapyrone A. (C) 2007 Published by Elsevier Ltd.
• Biomimetic synthesis of (±)-9,10-deoxytridachione
  作者：John E. Moses、Robert M. Adlington、Raphaël Rodriguez、Serena J. Eade、Jack E. Baldwin

  DOI：10.1039/b418988d

  日期：——

  A tandem Suzuki-coupling/electrocyclisation reaction sequence was employed for the biomimetic synthesis of (+/-)-9,10-deoxytridachione.

  串联的铃木-偶联/电环化反应序列用于（+/-）-9,10-脱氧三丁酮的仿生合成。