3-methyl-3-vinylmethylenecyclohexane | 3855-05-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 3-methyl-3-vinylmethylenecyclohexane
• 英文别名: 1-Methyl-3-methylen-1-vinyl-cyclohexan；1-ethenyl-1-methyl-3-methylidenecyclohexane
• CAS: 3855-05-8
• 化学式: C₁₀H₁₆
• 分子量: 136.237
• InChiKey: YIJFUWIZBRPXTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  3-methyl-3-vinylmethylenecyclohexane 在 zinc(II) chloride 正丁基锂 、 间氯过氧苯甲酸 作用下， 反应 1.42h， 生成 1-vinyl-1-methyl-3-<1'-phenylsulfonyl-2'-(2",6",6"-trimethylcyclohex-2"-enyl)ethyl>cyclohex-3-ene
  参考文献：
  名称：

  3-Substituted 1-vinyl-1-methylcyclohex-3-enes ? Precursors of tricyclic diterpenoids of the pimarane/rosane group

  摘要：

  The synthesis of 1-vinyl-1-methyl-3-chloromethylcyclohex-3-ene from 3-vinyl-3-methylcyclohexanone and the corresponding exomethylene derivative has been optimized and related allylsulfones prepared. By a standard combination of these compounds with the appropriate (cyclo)geranyl block synthones a series of regular functionalized diterpenoids has been prepared which are considered as likely precursors of the natural compounds indicated in the title.

  DOI：

  10.1007/bf00958567
• 作为产物：
  描述：

  5-Hydroxymethyl-1-methyl-cyclooct-1-en-acetat 生成 3-methyl-3-vinylmethylenecyclohexane
  参考文献：
  名称：

  153.桥接环系统。第四部分 涉及桥分裂的反应

  摘要：

  DOI：

  10.1039/jr9650000833

文献信息

• Cyclization of the 1,3-dimethyl-3-vinylcyclohexyl carbonium ion: a model for tetracyclic diterpene biosynthesis
  作者：Robert M. Coates、Han-Young Kang

  DOI：10.1039/c39870000232

  日期：——

  chloride at 100 °C followed by quenching with water afforded 2,4-dimethylbicyclo(2.2.2)octan-2-ol (6); the initial vinyl group cyclization (9)→(10) mimics the pimarenyl → beyeranyl cyclization step (2)→(3) postulated in the biosynthesis of the beyerane–Kaurane diterpenes.

  在100℃下将3-甲基-3-乙烯基亚甲基环己烷（5）萃取到氟磺酸-氟磺酰氯中，然后用水淬灭，得到2,4-二甲基双环（2.2.2）辛-2-醇（6）；最初的乙烯基环化（9）→（10）模仿了伯马瑞安-月桂烷二萜的生物合成中所假定的pimarenyl→铍烷基化步骤（2）→（3）。
• DRAGAN, V. A.;VESELOVSKIJ, V. V.;DAEVA, E. D.;MOISEENKOV, A. M., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 857-862
  作者：DRAGAN, V. A.、VESELOVSKIJ, V. V.、DAEVA, E. D.、MOISEENKOV, A. M.

  DOI：——

  日期：——
• RUSSELL, GLEN A.;YAO, CHING-FA;TASHTOUSH, HASAN I.;RUSSELL, JUNE E.;DEDOL+, J. ORG. CHEM., 56,(1991) N, C. 663-669
  作者：RUSSELL, GLEN A.、YAO, CHING-FA、TASHTOUSH, HASAN I.、RUSSELL, JUNE E.、DEDOL+

  DOI：——

  日期：——
• 153. Bridged ring systems. Part IV. Reactions involving bridge scission
  作者：G. L. Buchanan、A. McKillop、R. A. Raphael

  DOI：10.1039/jr9650000833

  日期：——
• 3-Substituted 1-vinyl-1-methylcyclohex-3-enes ? Precursors of tricyclic diterpenoids of the pimarane/rosane group
  作者：V. A. Dragan、V. V. Veselovskii、E. D. Daeva、A. M. Moiseenkov

  DOI：10.1007/bf00958567

  日期：1991.4

  The synthesis of 1-vinyl-1-methyl-3-chloromethylcyclohex-3-ene from 3-vinyl-3-methylcyclohexanone and the corresponding exomethylene derivative has been optimized and related allylsulfones prepared. By a standard combination of these compounds with the appropriate (cyclo)geranyl block synthones a series of regular functionalized diterpenoids has been prepared which are considered as likely precursors of the natural compounds indicated in the title.