1-甲氧基-4-(2,2,3,3-四甲基环丙基)苯 | 17953-95-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 环丁烷木脂素
• 中文名称: 1-甲氧基-4-(2,2,3,3-四甲基环丙基)苯
• 英文名称: 3-p-Anisyl-1,1,2,2-tetramethylcyclopropane
• 英文别名: 1-Methoxy-4-(2,2,3,3-tetramethylcyclopropyl)benzene
• CAS: 17953-95-6
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: UMCCCEHMZIRWRW-UHFFFAOYSA-N

物化性质

• 沸点：
  74-78 °C(Press: 0.7 Torr)
• 密度：
  0.936±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-甲氧基-4-(2,2,3,3-四甲基环丙基)苯 、 甲醇 以11%的产率得到
  参考文献：
  名称：

  ZIMMERMAN, HOWARD E.;HEYDINGER, JENIFER A., J. ORG. CHEM., 56,(1991) N, C. 1747-1758

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二甲基-2-丁烯 、 1-(重氮甲基)-4-甲氧基苯 在 zinc dibromide 作用下， 生成 1-甲氧基-4-(2,2,3,3-四甲基环丙基)苯
  参考文献：
  名称：

  Carbenoid decomposition of aryldiazomethanes with lithium and zinc halides. Synthesis of arylcyclopropanes

  摘要：

  DOI：

  10.1021/jo00838a008

文献信息

• Rearrangement of 1,3-diradicals. Arylcyclopropane photochemistry
  作者：Howard E. Zimmerman、Jenifer A. Heydinger

  DOI：10.1021/jo00005a018

  日期：1991.3

  The photochemistry of a series of aryl-substituted cyclopropanes was investigated as part of our continuing investigations of these systems. The literature held a puzzling discrepancy in which several similar reactants exhibited differing photochemistry. A series of 3-aryl-1,1,2,2-tetramethylcyclopropanes was found to rearrange photochemically to give primarily two types of products, the anticipated 4-aryl-2,3,3-trimethyl-1-butenes and, additionally, 1-aryl-2,3,3-trimethyl-1-butenes. The latter arise from regioselective methyl migration of intermediate singlet 1,3-diradicals. Also, the usual Griffin carbene fragmentation was encountered as a minor pathway. Biphenylyl-, p-cyanophenyl-, and p-anisyl-substituted cyclopropanes were studied. Also, the photochemistry of 3-phenyl-1,1,2,2-tetramethylcyclopropane was reinvestigated and found to conform to the general pattern of reactivity. Throughout, it was the singlet excited states responsible for the observed reactivity, and the triplet counterparts were found to be unreactive. In addition, the photochemistry of 3-biphenylyl-2,2-dimethyl-1,1-diphenylcyclopropane was studied. Again, the triplet was unreactive. The singlet gave rise to 4-biphenylyl-2-methyl-3,3-diphenyl-1-butene exclusively. The differing behavior of the various arylcyclopropanes is discussed from a mechanistic viewpoint. In the case of the 3-aryl-1,1,2,2-tetramethylcyclopropanes, the regioselectivity of the 1,3-diradical intermediate favors migration toward the less delocalized odd-electron center. This selectivity is understood on a quantum mechanical basis. Finally, quantum yields are reported.