1-methyl-4-(1-methylcyclopropyl)-1-cyclohexene | 60059-22-5

• 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-4-(1-methylcyclopropyl)-1-cyclohexene
• 英文别名: 4-(1-Methylcyclopropyl)-1-methylcyclohexene；(R)-1-methyl-4-(1-methyl-cyclopropyl)-cyclohexene；(R)-1-Methyl-4-(1-methyl-cyclopropyl)-cyclohexen；(+/-)-4-<1-Methyl-cyclopropyl>-1-methyl-cyclohex-1-en；4-(1-Methyl-cyclopropyl)-1-methyl-cyclohexen；1-Methyl-4-(1-methylcyclopropyl)cyclohexene
• CAS: 60059-22-5
• 化学式: C₁₁H₁₈
• 分子量: 150.264
• InChiKey: ISLDTUIMRRJVRV-UHFFFAOYSA-N

物化性质

• 沸点：
  73 °C(Press: 8.5 Torr)
• 密度：
  0.921±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  二碘甲烷 、 甜橙提取物 在 乙醚 、 coppered zinc 作用下， 生成 1-methyl-4-(1-methylcyclopropyl)-1-cyclohexene
  参考文献：
  名称：

  Notes: Simplified Zinc-Copper Couple for Use in Preparing Cyclopropanes from Methylene Iodide and Olefins

  摘要：

  DOI：

  10.1021/jo01093a630

文献信息

• Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes
  作者：You-Yun Zhou、Christopher Uyeda

  DOI：10.1002/anie.201511271

  日期：2016.2.24

  Dinuclear Ni complexes supported by naphthyridine‐diimine (NDI) ligands catalyze the reductive cyclopropanation of alkenes with CH2Cl2 as the methylene source. The use of mild terminal reductants (Zn or Et2Zn) confers significant functional‐group tolerance, and the catalyst accommodates structurally and electronically diverse alkenes. Mononickel catalysts bearing related N chelates afford comparatively

  萘啶二亚胺（NDI）配体支持的双核Ni络合物以CH 2 Cl 2为亚甲基源催化烯烃的还原环丙烷化。使用温和的末端还原剂（Zn或Et 2 Zn）可赋予显着的官能团耐受性，并且该催化剂可容纳结构和电子形式多样的烯烃。带有相关N螯合物的单镍催化剂提供相对较低的环丙烷收率（≤20％）。这些结果构成了从氧化的亚甲基前体进入催化卡宾转化的进入。
• Photochemistry of alkyl halides—VII
  作者：Paul J. Kropp、Norbert J. Pienta、Joy A. Sawyer、Richard P. Polniaszek

  DOI：10.1016/s0040-4020(01)92370-1

  日期：——

  The previously observed cyclopropaoation of alkenes by irradiation of diiodomethane (I) in their presence has been studied in more detail and found to be a synthetically useful procedure which is significantly less subject to steric effects than the traditional Simmons-Smith method. The results from photocyclopropanation of a variety of alkenes are summarized in Tables 1 and 3–4. In a number of cases

  先前观察到的通过二碘甲烷的辐射对烯烃的环丙烷化反应（I）的存在，我们对其进行了更详细的研究，发现它是一种合成上有用的方法，与传统的Simmons-Smith方法相比，其受到的空间位阻明显更少。表1和表3-4汇总了各种烯烃的光环丙烷化结果。在许多情况下，光化学程序提供的结果优于Simmons-Smith方法，尤其是使用空间拥挤的烯烃时。环烯烃显示的光环丙烷化相对速率是环大小的函数，类似于Simmons-Smith方法（表5）。然而，与Simmons-Smith方法相比，光环丙烷化反应的相对速率随着双键取代度的增加而稳定增加（表6），其中空间效应抵消了随着取代作用的增加烯烃的亲核性的提高。α碘化建议使用2作为亚甲基转移物质。在溴化锂存在下，将阳离子2捕集，得到溴碘甲烷。
• A New Synthesis of Cyclopropanes¹
  作者：Howard E. Simmons、Ronald D. Smith

  DOI：10.1021/ja01525a036

  日期：1959.8
• Cyclopropanation of Terminal Olefins Using Diazomethane/Palladium(II) Acetate
  作者：Minoru Suda

  DOI：10.1055/s-1981-29572

  日期：——
• Regioselectivity and solvent effects in cyclopropanation of alkadienes
  作者：Edwin C. Friedrich、Fatemeh Niyati-Shirkhodaee

  DOI：10.1021/jo00006a044

  日期：1991.3

  A comparison of the regioselectivities for monocyclopropanation of limonene and 4-vinylclohexene using diiodomethane with zinc dust and copper(I) chloride in ether, with diethylzinc in toluene, or with triethylaluminum in toluene-dichloromethane has been carried out. Some studies were also done using dibromomethane with zinc dust and copper(I) chloride in ether. The procedure using diethylzinc in toluene exhibited the least steric hindrance toward cyclopropanation at more highly substituted, electron-rich double bonds. In a study of solvent effects on the diiodomethane, zinc dust, and copper(I) chloride procedure, use of diisopropyl ether as a reaction solvent proved to be a satisfactory method for almost doubling the steric requirements of the cyclopropanating reagent.