1,3-dimethyl-3-phenylcyclopropene | 474657-78-8

• 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: 1,3-dimethyl-3-phenylcyclopropene
• 英文别名: Cyclopropene, 2,3-dimethyl-3-phenyl-；(1,2-dimethylcycloprop-2-en-1-yl)benzene
• CAS: 474657-78-8
• 化学式: C₁₁H₁₂
• 分子量: 144.216
• InChiKey: QSFWBTDJFNNDLW-UHFFFAOYSA-N

物化性质

• 沸点：
  193.4±15.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  1,3-dimethyl-3-phenylcyclopropene 、 三正丁基氢锡 在 [(CH₂CHCH₂)PdCl]2 、 2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到
  参考文献：
  名称：

  Transition Metal-Catalyzed Hydro-, Sila-, and Stannastannation of Cyclopropenes:  Stereo- and Regioselective Approach toward Multisubstituted Cyclopropyl Synthons

  摘要：

  The first highly efficient, stereo- and regioselective palladium-catalyzed hydro-, sila-, and stannastannation of cyclopropenes to give multisubstituted cyclopropylstannanes have been developed. It was shown that the addition across the double bond of cyclopropene is generally controlled by steric factors and proceeds from the least hindered face. The directing effect of alkoxymethyl substituents in the hydrostannation reaction of 3,3-disubstituted cyclopropenes was demonstrated. This methodology represents a powerful and atom-economic approach toward a wide variety of highly substituted cyclopropylstannanes, important building blocks unavailable by other methods.

  DOI：

  10.1021/ja027095k
• 作为产物：
  描述：

  1-甲基-1-苯基-2-溴环丙烷 在 氢氧化钾 、 正丁基锂 、 potassium tert-butylate 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 1,3-dimethyl-3-phenylcyclopropene
  参考文献：
  名称：

  Transition Metal-Catalyzed Hydro-, Sila-, and Stannastannation of Cyclopropenes:  Stereo- and Regioselective Approach toward Multisubstituted Cyclopropyl Synthons

  摘要：

  The first highly efficient, stereo- and regioselective palladium-catalyzed hydro-, sila-, and stannastannation of cyclopropenes to give multisubstituted cyclopropylstannanes have been developed. It was shown that the addition across the double bond of cyclopropene is generally controlled by steric factors and proceeds from the least hindered face. The directing effect of alkoxymethyl substituents in the hydrostannation reaction of 3,3-disubstituted cyclopropenes was demonstrated. This methodology represents a powerful and atom-economic approach toward a wide variety of highly substituted cyclopropylstannanes, important building blocks unavailable by other methods.

  DOI：

  10.1021/ja027095k

文献信息

• Cobalt-catalyzed multisubstituted allylation of the chelation-assisted C–H bond of (hetero)arenes with cyclopropenes
  作者：Kuppan Ramachandran、Pazhamalai Anbarasan

  DOI：10.1039/d1sc03476f

  日期：——

  Cp*Co^III-catalyzed ring-opening isomerization of cyclopropenes to cobalt vinylcarbene has been utilized for the synthesis of multisubstituted allylarenes via directing group-assisted functionalization of C–H bonds of arenes and heteroarenes.

  Cp*Co^III催化的环丙烯环开合异构化反应已被用于合成多取代烯丙基芳烃，通过芳烃和杂芳烃的C-H键的定向基辅助官能化。
• Rhodium-Catalyzed Hydroformylation of Cyclopropenes
  作者：William M. Sherrill、Michael Rubin

  DOI：10.1021/ja805059f

  日期：2008.10.15

  The first catalytic diastereo- and enantioselective hydroformylation of cyclopropenes was demonstrated. The reaction proceeds efficiently under very mild conditions and low catalyst loadings providing high yields of cyclopropylcarboxaldehydes. This novel methodology represents a convenient, atom-economic approach toward optically active cyclopropylcarboxaldehydes from readily available prochiral cyclopropenes.