(2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol | 866476-35-9

• 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: (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol
• 英文别名: (2E,4Z)-6-benzyloxy-4-bromohexa-2,4-dien-1-ol；(2E,4Z)-4-bromo-6-phenylmethoxyhexa-2,4-dien-1-ol
• CAS: 866476-35-9
• 化学式: C₁₃H₁₅BrO₂
• 分子量: 283.165
• InChiKey: SVWLLYARYRTRNI-XOHVCTMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol 在 copper(I) bromide dimethylsulfide complex 、 二甲基硫 、 偶氮二甲酸二叔丁酯 、 三氧化硫吡啶 、 四氯化钛 、 二异丁基氢化铝 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 10.5h， 生成
  参考文献：
  名称：

  A Racemic Synthesis of an AB-Ring System of Hexacyclinic Acid

  摘要：

  An AB-ring system of the polyketide natural product hexacyclinic acid has been synthesized in racemic form. The key steps were an intramolecular Diels-Alder cyclization of an ester tethered 1,3-nonadiene-8-yne, which generated the B-ring, and a samarium diiodide mediated reductive annulation, which was used to form the A-ring.

  DOI：

  10.1021/ol051633r
• 作为产物：
  描述：

  苄氧基乙醛 在 四(三苯基膦)钯 、 Ti₂CO₃ 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 59.0h， 生成 (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol
  参考文献：
  名称：

  An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol

  摘要：

  An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol has been devised. This new route increases the throughput and yield of the diene product by circumventing a low yielding preparation of boronic acid intermediate as well as removing the need to use multi-gram quantities of highly toxic thallium salts. In the process of developing this new route, a higher yielding preparation of ( E)-3-hydroxyprop-1-enylboronic acid was also achieved. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.071

文献信息

• An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol
  作者：Paul A. Clarke、Gabriele A. Rolla、Andrew P. Cridland、Andrew A. Gill

  DOI：10.1016/j.tet.2007.06.071

  日期：2007.9

  An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol has been devised. This new route increases the throughput and yield of the diene product by circumventing a low yielding preparation of boronic acid intermediate as well as removing the need to use multi-gram quantities of highly toxic thallium salts. In the process of developing this new route, a higher yielding preparation of ( E)-3-hydroxyprop-1-enylboronic acid was also achieved. (c) 2007 Elsevier Ltd. All rights reserved.
• A Racemic Synthesis of an AB-Ring System of Hexacyclinic Acid
  作者：Paul A. Clarke、Andrew P. Cridland

  DOI：10.1021/ol051633r

  日期：2005.9.1

  An AB-ring system of the polyketide natural product hexacyclinic acid has been synthesized in racemic form. The key steps were an intramolecular Diels-Alder cyclization of an ester tethered 1,3-nonadiene-8-yne, which generated the B-ring, and a samarium diiodide mediated reductive annulation, which was used to form the A-ring.