(1-methyl-1-cyclopropylmethylene)cyclopropane | 176172-19-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (1-methyl-1-cyclopropylmethylene)cyclopropane
• 英文别名: 1-(cyclopropylidenemethyl)-1-methylcyclopropane；(Cyclopropylidenemethyl)-1-methylcyclopropane
• CAS: 176172-19-3
• 化学式: C₈H₁₂
• 分子量: 108.183
• InChiKey: HVHDCMNMTBZADP-UHFFFAOYSA-N

物化性质

• 沸点：
  123.1±7.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  三乙基硅烷 、 (1-methyl-1-cyclopropylmethylene)cyclopropane 在 RhCl(PPh₃)3 作用下， 生成 (Z)-5-Triethylsilyl-2-cyclopropyl-2-pentene
  参考文献：
  名称：

  CC bond activation of cyclopropane ring in hydrosilylation catalyzed by wilkinson complex

  摘要：

  The new synthetic approach to silylated alkenes based on RhCl(PPh(3))(3) catalyzed hydrosilylation of vinylcyclopropanes is proposed. The mechanism of cyclopropane ring opening is discussed.

  DOI：

  10.1016/0040-4039(95)01628-u
• 作为产物：
  描述：

  spiro<6,6-dimethyl-2,3-diazobicyclo<3.1.0>hex-2-ene-4,1'-cyclopropane> 以 正己烷 为溶剂， 生成 (1-methyl-1-cyclopropylmethylene)cyclopropane 、 cis-1-cyclopropyl-3-methyl-1,3-butadiene 、 5,5-dimethyl-3-methylenecyclopent-1-ene 、 1-methyl-2'-methylenebicyclopropyl
  参考文献：
  名称：

  Thermal decomposition of strained spiro(1-pyrazoline-3,1?-cyclopropanes)

  摘要：

  Pyrolysis (320-370 degrees C) of polycyclic 1-pyrazolines 1 and 2, obtained by 1,3-dipolar cycloaddition of diazocyclopropane to 3,3-dimethylcyclopropene and spiro[2,3]hex-1-ene, yields complex mixtures of isomeric hydrocarbons, substituted methylenecyclopropanes being the main components. Pyrolysis of 6-ethenyl- (4) and 6-methoxy-6-methylcarbonyl-4,5-diazaspiro[2,4]hept-4-enes (6) at 310-320 degrees C proceeds more unambiguously to give vinyl- (18) and 1-methoxy-1-methylcarbonylspiropentanes (20) in similar to 85 and 95 % yields with respect to the transformed pyrazolines. Dediazotization of pyrazoline 3 obtained from diazocyclopropane and benzvalene requires more drastic conditions (similar to 440 degrees C) and produces indane.

  DOI：

  10.1007/bf00696714

文献信息

• [5+1] Cocyclization of (Cyclopropylmethylene)cyclopropanes and other Vinylcyclopropanes with Carbon Monoxide Catalyzed by Octacarbonyldicobalt
  作者：Armin de Meijere、Takuya Kurahashi

  DOI：10.1055/s-2005-917102

  日期：——

  Vinylcyclopropanes react with octacarbonyldicobalt ­stoichiometrically under mild conditions to give cyclohex-3-enones in moderate to good yields (51-75%). Catalytic amounts of the cobalt­carbonyl complex or a rhodiumcarbonyl complex also ­mediate [5+1] cocyclizations of vinylcyclopropanes with carbon monoxide (under CO balloon pressure) to give cyclohex-3-enones in good yields (up to 95%).

  在温和的条件下，乙烯基环丙烷与八羰基二钴按比例发生反应，生成中到高产率（51-75%）的环己-3-烯酮。催化量的羰基钴络合物或羰基铑络合物还能介导乙烯基环丙烷与一氧化碳（在一氧化碳气球压力下）发生 [5+1] 环化反应，从而以良好的收率（高达 95%）生成环己-3-烯酮。