2-(Cyclopropylidenemethyl)-1-ethenylnaphthalene | 197015-47-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(Cyclopropylidenemethyl)-1-ethenylnaphthalene
• CAS: 197015-47-7
• 化学式: C₁₆H₁₄
• 分子量: 206.287
• InChiKey: FOTHCBRJPMLNLU-UHFFFAOYSA-N

物化性质

• 沸点：
  373.9±12.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-(Cyclopropylidenemethyl)-1-ethenylnaphthalene 在 tetrafluoroboric acid 、 间氯过氧苯甲酸 作用下， 生成 2-(1-Ethenylnaphthalen-2-yl)cyclobutan-1-one
  参考文献：
  名称：

  A Novel Palladium-Mediated Cascade Reaction Triggered by Strain Release of the Cyclobutane System. A New General Route to Benzo- and Naphthohydrindans

  摘要：

  A novel palladium-mediated cascade reaction was reported. By this procedure, the olefinic cyclobutanols 17, 24, and 31; 41; 37; and 45 afforded the benzo-and naphthohydrindans (46-49, 50-53, 54-57, and 58-61) respectively in one operation in the ratios depending on the mediators and solvents employed. This provides a novel and efficient synthesis of biologically important A-nor and C-11-alkylated steroids.

  DOI：

  10.1021/jo971377z
• 作为产物：
  描述：

  1-羟基-2-奈甲醛 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 sodium hydride 、 lithium chloride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成 2-(Cyclopropylidenemethyl)-1-ethenylnaphthalene
  参考文献：
  名称：

  A Novel Palladium-Mediated Cascade Reaction Triggered by Strain Release of the Cyclobutane System. A New General Route to Benzo- and Naphthohydrindans

  摘要：

  A novel palladium-mediated cascade reaction was reported. By this procedure, the olefinic cyclobutanols 17, 24, and 31; 41; 37; and 45 afforded the benzo-and naphthohydrindans (46-49, 50-53, 54-57, and 58-61) respectively in one operation in the ratios depending on the mediators and solvents employed. This provides a novel and efficient synthesis of biologically important A-nor and C-11-alkylated steroids.

  DOI：

  10.1021/jo971377z

文献信息

• Asymmetric total synthesis of (+)-equilenin utilizing two types of cascade ring expansion reactions of small ring systems
  作者：Masahiro Yoshida、Mohamed Abdel-Hamid Ismail、Hideo Nemoto、Masataka Ihara

  DOI：10.1039/b003578p

  日期：——

  Enantioselective synthesis of (+)-equilenin 1 utilizing two types of cascade ring expansion reactions of small ring systems is described. The first key step is an asymmetric epoxidation–ring expansion reaction of cyclopropylidene derivatives to afford chiral cyclobutanones. We found that both the fructose-derived chiral ketone and the chiral (salen)Mn(III) complex were effective catalysts for the asymmetric

  描述了利用小环系统的两种类型的级联环膨胀反应的（+）-quileninin 1的对映选择性合成。第一步是环亚丙基衍生物的不对称环氧化-环扩环反应，以提供手性环丁酮。我们发现果糖衍生的手性 酮和手性（salen）Mn（III）配合物是有效的催化剂对于不对称感应。第二个关键步骤是钯促进级联 扩环–分子内 插入反应 异丙烯基环丁醇。 溶剂类是造成非对映选择性形成氢化茚的重要因素。通过利用这些方法，已经完成了（+）-quilenin 1的不对称全合成。