6-tert-butyl-6-methylfulvene | 7301-17-9

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 6-tert-butyl-6-methylfulvene
• 英文别名: 5-(3,3-Dimethylbutan-2-ylidene)cyclopenta-1,3-diene
• CAS: 7301-17-9
• 化学式: C₁₁H₁₆
• 分子量: 148.248
• InChiKey: QVRMHWYOGBLZNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  6-tert-butyl-6-methylfulvene 以 氯仿 、 xylene 为溶剂， 反应 7.0h， 生成 (3aR,9aR)-3-[1,2,2-Trimethyl-prop-(E)-ylidene]-3,3a,6,9a-tetrahydro-cyclopenta[a]azulene-9,9-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  缺电子的七富烯与富电子富烯的不对称环加成中的环外取代基效应：立体选择性，周选择性和区域选择性

  摘要：

  讨论了电子不足的七氟醚与富电子富烯的不对称环加成反应中立体选择性，周选择性和区域选择性的环外取代基控制。

  DOI：

  10.1016/s0040-4020(97)10190-9
• 作为产物：
  描述：

  环戊二烯 、 频哪酮 在 sodium 作用下， 以 乙醇 为溶剂， 生成 6-tert-butyl-6-methylfulvene
  参考文献：
  名称：

  Generation and Characterization of Alkyl-Substituted m-Xylylenes in Fluid Solution at Room Temperature

  摘要：

  Fluoride ion induced generation of isobutylidene from isopropyl trimethylsiiyl ketone enol triflate in the presence of 6,6-dimethylfulvene gives the [2.2]-m-cyclophane dimer of alpha,alpha,alpha'alpha'-tetramethyl-m-xylylene. When isobutylidene is added to 6,6-bis(trideuteriomethyl)fulvene, the C-13 NMR spectrum of the dimer reveals three quaternary carbons in a 1:1:1 ratio, progressively shifted upfield to suggest that two dimers are formed. Saturation of the reactant solutions with dioxygen resulted in no dimer formation despite undiminished loss of reactants. A control experiment indicated that dioxygen does not affect the formation of the methylenecyclopropane from cyclohexene and isobutylidene. Reaction of 6-cyclopropyl-6-methylfulvene with isobutylidene gave dimers with intact cyclopropane rings. Addition of isobutylidene to 6-tert-butyl-6-methylfulvene resulted in a non-cyclophane dimer.

  DOI：

  10.1021/ja00091a018

文献信息

• On the conformation of 8-substituted bicyclo [3.2.1] oct-6-en-3-ones
  作者：Y. Kashman、A. Rudi

  DOI：10.1016/s0040-4020(01)97224-2

  日期：1974.1
• Gajewski Joseph J., Paul Gitendra C., Chang Ming Jing, Gortva Andrea M., J. Amer. Chem. Soc, 116 (1994) N 12, S 5150-5154
  作者：Gajewski Joseph J., Paul Gitendra C., Chang Ming Jing, Gortva Andrea M.

  DOI：——

  日期：——
• Generation and Characterization of Alkyl-Substituted m-Xylylenes in Fluid Solution at Room Temperature
  作者：Joseph J. Gajewski、Gitendra C. Paul、Ming Jing Chang、Andrea M. Gortva

  DOI：10.1021/ja00091a018

  日期：1994.6

  Fluoride ion induced generation of isobutylidene from isopropyl trimethylsiiyl ketone enol triflate in the presence of 6,6-dimethylfulvene gives the [2.2]-m-cyclophane dimer of alpha,alpha,alpha'alpha'-tetramethyl-m-xylylene. When isobutylidene is added to 6,6-bis(trideuteriomethyl)fulvene, the C-13 NMR spectrum of the dimer reveals three quaternary carbons in a 1:1:1 ratio, progressively shifted upfield to suggest that two dimers are formed. Saturation of the reactant solutions with dioxygen resulted in no dimer formation despite undiminished loss of reactants. A control experiment indicated that dioxygen does not affect the formation of the methylenecyclopropane from cyclohexene and isobutylidene. Reaction of 6-cyclopropyl-6-methylfulvene with isobutylidene gave dimers with intact cyclopropane rings. Addition of isobutylidene to 6-tert-butyl-6-methylfulvene resulted in a non-cyclophane dimer.
• Exocyclic substituent effects in the unsymmetrically cycloadditions of electron-deficient heptafulvenes with electron-rich fulvenes: Stereoselectivity, periselectivity, and regioselectivity
  作者：Ching-Yang Liu、Huei-Yan Shie、Shin-Yi Chen、Chiung-Yi You、Wei-Chang Wang、Liang-Neng Hua、He-Jiun Yang、Chih-Min Tseng

  DOI：10.1016/s0040-4020(97)10190-9

  日期：1997.12

  The exocyclic substituent control of stereoselectivity, periselectivity, and regioselectivity in the unsymmetrical cycloaddition reactions of electron-deficient heptafulvenes with electron-rich fulvenes are discussed.

  讨论了电子不足的七氟醚与富电子富烯的不对称环加成反应中立体选择性，周选择性和区域选择性的环外取代基控制。