8-bromobicyclo[5.1.0]oct-1(8)-ene | 87619-37-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 8-bromobicyclo[5.1.0]oct-1(8)-ene
• CAS: 87619-37-2
• 化学式: C₈H₁₁Br
• 分子量: 187.079
• InChiKey: SXQPUNSDQSHKEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  9.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  8-bromobicyclo[5.1.0]oct-1(8)-ene 在 氨 、 sodium 、 氯化铵 作用下， 以 乙醚 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  The Synthesis and Chemistry of 8-Substituted Bicyclo[5.1.0]oct-1(8)-ene

  摘要：

  Abstract8‐Bromobicyclo[5.1.0]oct‐1(8)‐cne (7), an intermediate for the preparation of 8‐substituted bicyclo[5.1.0]oct‐1(8)‐enes, was synthesized by denomination of 1,8,8‐tribromobicyclo[5.1.0]octane (6). Compound 7 underwent bromo‐lithium exchange followed by nucleophilic substitution reactions to generate bicyclo[5.1.0]oct‐1(8)‐ene (5), 8‐methylbicyclo[5.1.0]oct‐1(8)‐ene (10), and 8‐trimethylsilylbicyclo[5.1.0]oct‐1(8)‐ene (11). The bicyclic cyclopropenes 7, 5, 10, and 11 reacted with cyclopentadiene to form adducts 12, 13, 14, and 15, respectively. All of these Diels‐Alder adducts are endo‐exo isomers (endo‐addition from the view of the cyclopropene and exo‐addition from the view of the cyclooctene).

  DOI：

  10.1002/jccs.199800060
• 作为产物：
  描述：

  1,8,8-tribromobicyclo[5.1.0]octane 在 甲基锂 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 8-bromobicyclo[5.1.0]oct-1(8)-ene
  参考文献：
  名称：

  The Synthesis and Chemistry of 8-Substituted Bicyclo[5.1.0]oct-1(8)-ene

  摘要：

  Abstract8‐Bromobicyclo[5.1.0]oct‐1(8)‐cne (7), an intermediate for the preparation of 8‐substituted bicyclo[5.1.0]oct‐1(8)‐enes, was synthesized by denomination of 1,8,8‐tribromobicyclo[5.1.0]octane (6). Compound 7 underwent bromo‐lithium exchange followed by nucleophilic substitution reactions to generate bicyclo[5.1.0]oct‐1(8)‐ene (5), 8‐methylbicyclo[5.1.0]oct‐1(8)‐ene (10), and 8‐trimethylsilylbicyclo[5.1.0]oct‐1(8)‐ene (11). The bicyclic cyclopropenes 7, 5, 10, and 11 reacted with cyclopentadiene to form adducts 12, 13, 14, and 15, respectively. All of these Diels‐Alder adducts are endo‐exo isomers (endo‐addition from the view of the cyclopropene and exo‐addition from the view of the cyclooctene).

  DOI：

  10.1002/jccs.199800060

文献信息

• 1-halocyclopropenes and propargylic halides from the reaction of trihalocyclopropanes with methyl lithium
  作者：Mark S. Baird、William Nethercott

  DOI：10.1016/s0040-4039(00)81476-8

  日期：1983.1

  1,1,2-Trihalocyclopropanes (halogen = chlorine or bromine) undergo 1,2-dehalogenation on reaction with methyl lithium, and in a number of cases the product is a 1-halocyclopropene. In the reactions of (20, X = Br, Cl) and (25) a rearrangement occurs even at low temperatures and propargylic halides are isolated, while (16) is converted to 2-chlorocyclohex-2-enylidene which may be trapped by furan.

  1,1,2-三卤代环丙烷（卤素=氯或溴）在与甲基锂反应时会进行1,2-脱卤作用，在许多情况下，产物是1-卤代环丙烯。在（20，X = Br，Cl）和（25）的反应中，即使在低温下也会发生重排，并分离出炔丙基卤，而（16）转化为2-氯环己-2-烯基，可能被呋喃捕获。
• Pyridazines by addition of diazoalkanes to 1-bromo- and 1,2-dibromocyclopropenes
  作者：Ahmad R. Al Dulayymi、Mark S. Baird

  DOI：10.1016/s0040-4020(98)00781-9

  日期：1998.10

  Reaction of a range of 1-bromocyclopropenes with diazo-compounds leads to pyrazoles which ring-open to pyridazines in reasonable yield.

  一系列的1-溴环丙烯与重氮化合物的反应生成吡唑，其以合理的收率对哒嗪开环。