2-methyl-3-bromomethyl-1,6-heptadiene | 66348-53-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 2-methyl-3-bromomethyl-1,6-heptadiene
• 英文别名: 3-bromomethyl-2-methyl-hepta-1,6-diene；3-(Bromomethyl)-2-methyl-1,6-heptadiene；3-(bromomethyl)-2-methylhepta-1,6-diene
• CAS: 66348-53-6
• 化学式: C₉H₁₅Br
• 分子量: 203.122
• InChiKey: KOANEYRRRXIUAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-methyl-3-bromomethyl-1,6-heptadiene 在 吡啶 作用下， 生成 (+/-)-(Z)-3-methyl-6-isopropenyl-3,9-decadien-1-ol acetate
  参考文献：
  名称：

  Highly efficient terpenoid pheromone syntheses via regio- and stereocontrolled processing of allyllithiums generated by reductive lithiation of allyl phenyl thioethers

  摘要：

  Previous work had shown that reductive lithiation of allyl phenyl thioethers, followed by transmetallation, produces allylmetallics which react selectively with carbonyl compounds at the most or least substituted terminus; the latter results in mainly cis olefin. This technology allows extremely efficient syntheses of racemic versions of lavandulol (two-pot, 70% yield), the Comstock mealy bug pheromone (one-pot, 45% yield) and the California red scale pheromone (4-steps, 23% yield).

  DOI：

  10.1016/s0040-4020(01)80712-2
• 作为产物：
  描述：

  3-甲基-2-丁烯酸乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 生成 2-methyl-3-bromomethyl-1,6-heptadiene
  参考文献：
  名称：

  A highly stereoselective synthesis of Z-trisubstituted olefins via [2,3]-sigmatropic rearrangement. Preference for a pseudoaxially substituted transition state

  摘要：

  DOI：

  10.1021/ja00474a049

文献信息

• PROCESS FOR PREPARING 6-ISOPROPENYL-3-METHYL-9-DECENYL ACETATE AND INTERMEDIATES THEREOF
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20210323903A1

  公开（公告）日：2021-10-21

  A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M 1 represents Li, MgZ 1 , ZnZ 1 , Cu, CuZ 1 , or CuLiZ 1 , wherein Z 1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X 1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3).

  以下是该过程的中文翻译：制备下列式（3）的6-异丙烯基-3-甲基-9-癸烯基醋酸酯的制备过程，其中Ac代表乙酰基，该过程包括以下步骤：制备亲核试剂，下列一般式（1）的5-异丙烯基-2-甲基-8-壬烯基化合物：其中M1代表Li，MgZ1，ZnZ1，Cu，CuZ1或CuLiZ1，其中Z1代表卤素原子或5-异丙烯基-2-甲基-8-壬烯基基团，从下列一般式（4）的5-异丙烯基-2-甲基-8-壬烯基卤化物化合物制备：其中X1代表卤素原子；将亲核试剂（1）5-异丙烯基-2-甲基-8-壬烯基化合物与选择自甲醛、多聚甲醛和1,3,5-三噁烷的至少一种亲电试剂进行加成反应，随后进行水解反应以形成下列式（2）的6-异丙烯基-3-甲基-9-癸烯醇；并对6-异丙烯基-3-甲基-9-癸烯醇（2）进行乙酰化以形成6-异丙烯基-3-甲基-9-癸烯基醋酸酯（3）。
• A highly stereoselective synthesis of Z-trisubstituted olefins via [2,3]-sigmatropic rearrangement. Preference for a pseudoaxially substituted transition state
  作者：W. Clark Still、Abhijit Mitra

  DOI：10.1021/ja00474a049

  日期：1978.3
• Highly efficient terpenoid pheromone syntheses via regio- and stereocontrolled processing of allyllithiums generated by reductive lithiation of allyl phenyl thioethers
  作者：Dennis W. McCullough、M. Bhupathy、Elvio Piccolino、Theodore Cohen

  DOI：10.1016/s0040-4020(01)80712-2

  日期：1991.12

  Previous work had shown that reductive lithiation of allyl phenyl thioethers, followed by transmetallation, produces allylmetallics which react selectively with carbonyl compounds at the most or least substituted terminus; the latter results in mainly cis olefin. This technology allows extremely efficient syntheses of racemic versions of lavandulol (two-pot, 70% yield), the Comstock mealy bug pheromone (one-pot, 45% yield) and the California red scale pheromone (4-steps, 23% yield).