2-Bromo-1,5-heptadien-4-ol | 138416-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Bromo-1,5-heptadien-4-ol
• 英文别名: (5E)-2-bromohepta-1,5-dien-4-ol
• CAS: 138416-10-1
• 化学式: C₇H₁₁BrO
• 分子量: 191.068
• InChiKey: GBFMLXSEAVFZIN-ONEGZZNKSA-N

物化性质

• 沸点：
  222.7±28.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Bromo-1,5-heptadien-4-ol 在 四(三苯基膦)钯 、 三甲基溴硅烷 、 甲基氯化镁 、 溴化铟(III) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.83h， 生成
  参考文献：
  名称：

  TMSBr/InBr₃-promoted Prins cyclization/homobromination of dienyl alcohol with aldehyde to construct cis-THP containing an exocyclic E-alkene

  摘要：

  一种由TMSBr/InBr₃促进的Prins环化/同溴化反应已开发，用于构建一种独特的cis-E THP，该THP显示为(-)-exiguolide中的A环和bryostatins中的B环。

  DOI：

  10.1039/c5cc06270e
• 作为产物：
  描述：

  巴豆醛 、 2,3-二溴-1-丙烯 在 tin 、 氢溴酸 作用下， 以 乙醚 、 水 为溶剂， 反应 4.0h， 以82%的产率得到2-Bromo-1,5-heptadien-4-ol
  参考文献：
  名称：

  TMSBr/InBr₃-promoted Prins cyclization/homobromination of dienyl alcohol with aldehyde to construct cis-THP containing an exocyclic E-alkene

  摘要：

  一种由TMSBr/InBr₃促进的Prins环化/同溴化反应已开发，用于构建一种独特的cis-E THP，该THP显示为(-)-exiguolide中的A环和bryostatins中的B环。

  DOI：

  10.1039/c5cc06270e

文献信息

• Stereodefined Substituted Cyclopropyl Zinc Reagents from Gem-Bismetallics
  作者：Dov Beruben、Ilane Marek、Jean F. Normant、Nicole Platzer

  DOI：10.1021/jo00113a032

  日期：1995.4

  1,1- or n,n-Bismetallic reagents bearing a methoxymethyl ether in the gamma position undergo cyclization at room temperature to give monometalated, diastereoselectively substituted cyclopropanes, The nature of the substituents is crucial for this diastereoselection, a pi-chelation between one metal and a properly located unsaturation, as well as 1,2-strain, are proposed to explain the steric outcome of these reactions.
• 1,4-Hydroiodination of Dienyl Alcohols with TMSI To Form Homoallylic Alcohols Containing a Multisubstituted <i>Z</i>-Alkene and Application to Prins Cyclization
  作者：Yongjin Xu、Zhiping Yin、Xinglong Lin、Zubao Gan、Yanyang He、Lu Gao、Zhenlei Song

  DOI：10.1021/acs.orglett.5b00485

  日期：2015.4.17

  A regioselective 1,4-hydroiodination of dienyl alcohols has been developed using trimethylsilyl iodide as Lewis acid and iodide source. A range of homoallylic alcohols containing a multisubstituted Z-alkene was synthesized with good to excellent configurational control. The approach was applied in sequential hydroiodination/Prins cyclization to afford multisubstituted tetrahydropyrans diastereoselectively.
• The organic synthesis using haloboration reaction 20. A simple synthesis of (2-Bromoallyl)diphenoxyborane by the bromoboration of allene and its reaction with carbonyl compounds
  作者：Shoji Hara、Akira Suzuki

  DOI：10.1016/s0040-4039(00)93593-7

  日期：1991.11

  Bromoboration reaction of allene with boron tribromide, followed by the treatment with anisole gives (2-bromoally)diphenoxyborane which reacts with aldehydes and ketones to give 2-bromohomoallylic alcohols in excellent yields.
• TMSBr/InBr₃-promoted Prins cyclization/homobromination of dienyl alcohol with aldehyde to construct cis-THP containing an exocyclic E-alkene
  作者：Linjie Li、Xianwei Sun、Yanyang He、Lu Gao、Zhenlei Song

  DOI：10.1039/c5cc06270e

  日期：——

  A TMSBr/InBr₃-promoted Prins cyclization/homobromination reaction of dienyl alcohol with aldehyde has been developed to construct a unique cis-E THP shown as the A ring in (−)-exiguolide and the B ring in bryostatins.

  一种由TMSBr/InBr₃促进的Prins环化/同溴化反应已开发，用于构建一种独特的cis-E THP，该THP显示为(-)-exiguolide中的A环和bryostatins中的B环。