2,6-Dimethyl-4-<(3-phenyl)propylidene>-2,5-cyclohexadien-1-one | 127311-27-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-Dimethyl-4-<(3-phenyl)propylidene>-2,5-cyclohexadien-1-one
• 英文别名: 2,6-dimethyl-4-(3-phenylpropylidene)-2,5-cyclohexadien-1-one；2,6-Dimethyl-4-(3-phenylpropylidene)cyclohexa-2,5-dien-1-one
• CAS: 127311-27-7
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: ZHEYYUUTAHSOGV-UHFFFAOYSA-N

物化性质

• 沸点：
  384.6±12.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-Dimethyl-4-<(3-phenyl)propylidene>-2,5-cyclohexadien-1-one 生成 (+/-)-1-(3,5-Dimethyl-4-hydroxyphenyl)-2,3-dihydroindene
  参考文献：
  名称：

  Angle Steven R., Arnaiz Damian O., Boyce James P., Frutos Rogelio P., Lou+, J. Org. Chem, 59 (1994) N 21, S 6322-6337

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(3,5-二甲基-4-羟基苯基)-3-苯基丙醇 在 lithium aluminium tetrahydride 、 三甲基溴硅烷 、 silver(l) oxide 作用下， 以 氘代氯仿 为溶剂， 反应 0.84h， 生成 2,6-Dimethyl-4-<(3-phenyl)propylidene>-2,5-cyclohexadien-1-one
  参考文献：
  名称：

  Formal [3+2]cycloaddition of benzylic cations with alkenes

  摘要：

  The reaction of benzylic cations with styrenes affords dihydro(1H)indenes in good yield via a formal [3 + 2] atom cycloaddition. The cations were generated from quinone methides and benzylic alcohols. (E)-Styrenes participate in the reaction with remarkable stereoselectivity affording dihydro(1H)indenes with three stereogenic centers with >40:1 diastereoselectivity. A possible transition state for the reaction is discussed. Less activated alkenes such as dihydropyran and methylcyclohexene afforded cycloadducts in 66% and 51% yields, respectively.

  DOI：

  10.1021/jo00048a029

文献信息

• Formation of Carbon-Carbon Bonds via Quinone Methide-Initiated Cyclization Reactions
  作者：Steven R. Angle、Damian O. Arnaiz、James P. Boyce、Rogelio P. Frutos、Michael S. Louie、Heather L. Mattson-Arnaiz、Jon D. Rainier、Kenneth D. Turnbull、Wenjin Yang

  DOI：10.1021/jo00100a039

  日期：1994.10

  p-Quinone methides were found to be excellent electrophilic cyclization initiators for the formation of six-membered rings. Cyclizations to form five- and seven-membered rings were also studied. Oxidation of 2,6-disubstituted phenols with Ag2O afforded the corresponding quinone methides. A wide range of cyclization terminators/nucleophiles were found to be effective in the cyclizations, including: allylsilane, beta-keto esters, furan, pyrrole, indole, and a number of alkenes. The yields of the cyclizations were generally high.
• Synthesis of dihydro-1H-indenes via a formal 3 + 2 cycloaddition of para-quinone methides and styrenes
  作者：Steven R. Angle、Damian O. Arnaiz

  DOI：10.1021/jo00299a003

  日期：1990.6
• Formal [3+2]cycloaddition of benzylic cations with alkenes
  作者：Steven R. Angle、Damian O. Arnaiz

  DOI：10.1021/jo00048a029

  日期：1992.10

  The reaction of benzylic cations with styrenes affords dihydro(1H)indenes in good yield via a formal [3 + 2] atom cycloaddition. The cations were generated from quinone methides and benzylic alcohols. (E)-Styrenes participate in the reaction with remarkable stereoselectivity affording dihydro(1H)indenes with three stereogenic centers with >40:1 diastereoselectivity. A possible transition state for the reaction is discussed. Less activated alkenes such as dihydropyran and methylcyclohexene afforded cycloadducts in 66% and 51% yields, respectively.
• Angle Steven R., Arnaiz Damian O., Boyce James P., Frutos Rogelio P., Lou+, J. Org. Chem, 59 (1994) N 21, S 6322-6337
  作者：Angle Steven R., Arnaiz Damian O., Boyce James P., Frutos Rogelio P., Lou+

  DOI：——

  日期：——