(Z)-7-(3,5-Dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)-1-phenyl-1-heptene | 149777-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-7-(3,5-Dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)-1-phenyl-1-heptene
• 英文别名: 2,6-dimethyl-4-[(Z)-7-phenylhept-6-enylidene]cyclohexa-2,5-dien-1-one
• CAS: 149777-50-4
• 化学式: C₂₁H₂₄O
• 分子量: 292.421
• InChiKey: JDAHSUFHOATTLK-XFFZJAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (Z)-7-(3,5-Dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)-1-phenyl-1-heptene 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (+/-)-(4aS^*,9S^*,9aS^*)-6,8-Dimethyl-7-hydroxy-9-phenyl-1,2,3,4,4a,9,9a-heptahydrofluorene 、 (+/-)-(4aS^*,9R^*,9aR^*)-6,8-Dimethyl-7-hydroxy-9-phenyl-1,2,3,4,4a,9,9a-heptahydrofluorene
  参考文献：
  名称：

  Intramolecular formal [3 + 2] cycloaddition of alkenes and benzylic cations. Stereoselective synthesis of 1,2,3,4,4a,9a-hexahydrofluorenes

  摘要：

  The Lewis acid-promoted intramolecular formal [3 + 2]-atom 'cycloaddition' of alkenes with benzylic cations derived from benzylic alcohols and quinone methides affords products in good yield and with remarkable stereoselectivity. Benzylic alcohol 20 affords hexahydrofluorene 36 with three new stereogenic centers in 73% yield as a 10:1 mixture of diastereomers. The scope and limitations of these reactions were explored by varying the substitution pattern on the benzylic cation, the cyclization initiators, and the alkene terminators.

  DOI：

  10.1021/jo00071a024
• 作为产物：
  描述：

  1-<(tert-Butyldimethylsilyl)oxy>-4-(6-bromohexyl)-2,6-dimethylbenzene 在 六甲基磷酰三胺 、 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 、 sodium iodide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷-D2 、 丙酮 为溶剂， 反应 33.92h， 生成 (Z)-7-(3,5-Dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)-1-phenyl-1-heptene
  参考文献：
  名称：

  Intramolecular formal [3 + 2] cycloaddition of alkenes and benzylic cations. Stereoselective synthesis of 1,2,3,4,4a,9a-hexahydrofluorenes

  摘要：

  The Lewis acid-promoted intramolecular formal [3 + 2]-atom 'cycloaddition' of alkenes with benzylic cations derived from benzylic alcohols and quinone methides affords products in good yield and with remarkable stereoselectivity. Benzylic alcohol 20 affords hexahydrofluorene 36 with three new stereogenic centers in 73% yield as a 10:1 mixture of diastereomers. The scope and limitations of these reactions were explored by varying the substitution pattern on the benzylic cation, the cyclization initiators, and the alkene terminators.

  DOI：

  10.1021/jo00071a024