2,2-二甲基-1,1-二苯基-3-(2,2-二苯基乙烯基)环丙烷 | 24149-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,2-二甲基-1,1-二苯基-3-(2,2-二苯基乙烯基)环丙烷
• 英文名称: 2,2-Dimethyl-1,1-diphenyl-3-(2,2-diphenylvinyl)cyclopropane
• 英文别名: 1,1-Diphenyl-2,2-dimethyl-3-(2,2-diphenylvinyl) cyclo-propane；[2-(2,2-dimethyl-3,3-diphenylcyclopropyl)-1-phenylethenyl]benzene
• CAS: 24149-62-0
• 化学式: C₃₁H₂₈
• 分子量: 400.563
• InChiKey: FNBCCDUAOVFIBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  2,2-二甲基-1,1-二苯基-3-(2,2-二苯基乙烯基)环丙烷 在 palladium on activated charcoal 氢气 作用下， 生成
  参考文献：
  名称：

  Novel photochemical 1,4-phenyl migration. Role of the second .pi. bond in the di-.pi.-methane rearrangement. Mechanistic and exploratory organic photochemistry

  摘要：

  DOI：

  10.1021/ja00823a022
• 作为产物：
  描述：

  1,1,5,5-Tetraphenyl-3,3-dimethyl-1,4-pentadien 生成 2,2-二甲基-1,1-二苯基-3-(2,2-二苯基乙烯基)环丙烷
  参考文献：
  名称：

  不同的取代基对二π-甲烷重排的速率和区域选择性的影响。新的光化学理论：激发分布（ΔP矩阵），垂直激发态稳定对反应的抑制，基态Vs。激发态控制

  摘要：

  在三个二-π-甲烷体系中观察到了通过取代基控制区域选择性的一致模式，但对速率的影响随体系的变化而变化。从这三个新概念中得出：（i）一种方法，该方法可让人们辨别最初和转化为产物时激发能在整个分子中是如何分配的；（ii）过度的垂直激发态稳定化可以抑制反应的证据；（iii）运动取决于基团上带有取代基的单元在反应超表面上的临界点是否被明显激发，激发或基态取代基的取代基对反应的影响。

  DOI：

  10.1039/c39780000228

文献信息

• Differing substituent effects on rates and regioselectivities in the di-π-methane rearrangement. New photochemical theory: excitation distribution (the ΔP matrix), reaction inhibition by vertical excited state stabilisation, ground Vs. excited state control
  作者：Howard E. Zimmerman、William T. Gruenbaum、Robert T. Klun、Mark G. Steinmetz、Thomas R. Welter

  DOI：10.1039/c39780000228

  日期：——

  consistent pattern of control of regioselectivity by substituents was observed in three di-π-methane systems while the effect on rates varied with the system; from this three new concepts were derived: (i) a method allowing one to discern how excitation energy is partitioned throughout a molecule initially and during transformation to product, (ii) evidence that excessive vertical excited state stablization

  在三个二-π-甲烷体系中观察到了通过取代基控制区域选择性的一致模式，但对速率的影响随体系的变化而变化。从这三个新概念中得出：（i）一种方法，该方法可让人们辨别最初和转化为产物时激发能在整个分子中是如何分配的；（ii）过度的垂直激发态稳定化可以抑制反应的证据；（iii）运动取决于基团上带有取代基的单元在反应超表面上的临界点是否被明显激发，激发或基态取代基的取代基对反应的影响。
• An assortment of highly unusual rearrangements in the photochemistry of vinylcyclopropanes. Mechanistic and exploratory organic photochemistry
  作者：Howard E. Zimmerman、Frank L. Oaks、Pedro Campos

  DOI：10.1021/ja00185a033

  日期：1989.2
• Mechanistic and exploratory organic photochemistry. XLI. Di-.pi.-methane rearrangement. Interaction of electronically excited vinyl chromophores
  作者：Howard E. Zimmerman、Patrick S. Mariano

  DOI：10.1021/ja01035a021

  日期：1969.3
• Photochemistry of Organic Molecules Entwined in Spiderwebs; The Use of Poly(methyl methacrylate) Glass for Restricting Excited-State Motion
  作者：Howard E. Zimmerman、Michael E. O'Brien

  DOI：10.1021/jo00086a036

  日期：1994.4

  A study of several unimolecular photochemical rearrangements in poly(methyl methacrylate) glass was carried out with the intent of comparing the behavior of excited-state species trapped in a polymer matrix with both the corresponding solution photochemistry and that in crystal lattices. Three reactants were studied: (a) 4,5,5-triphenylcyclohex-2-en-1-one, (b) 1,1-dicyano-3,3,5,5-tetraphenyl-1,4-pentadiene, and (c) 2,2-dimethyl-1,1-diphenyl-3-(2,2-diphenyl)cyclopropane. The solution photochemistry of the three compounds had previously been studied in our laboratory, and the photochemistry in the crystal lattice had been similarly investigated for the first two. The crystal lattice photochemistry of the last of the three was investigated in the present study. For each of the three reactants; different photochemical behavior was observed depending on the environment-polymer glass, solution, or crystal lattice. The experimental behavior correlated nicely with theoretical assessment of molecular motion of the component atoms in proceeding onward from that point along the reaction coordinate where multiple reaction pathways are available. The preferred reaction pathway proved consistently to require the least motion and the minimum molecular volume displacement. A concept of least motion dependent on its application to the ''branch point'' rather than the entire conversion of reactant to product was established.
• Novel photochemical 1,4-phenyl migration. Role of the second .pi. bond in the di-.pi.-methane rearrangement. Mechanistic and exploratory organic photochemistry
  作者：Howard E. Zimmerman、R. Daniel Little

  DOI：10.1021/ja00823a022

  日期：1974.8