1,1,2-triphenyl-3-methylcyclopropane | 130138-97-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,1,2-triphenyl-3-methylcyclopropane
• 英文别名: 2-methyl-1,1,3-triphenylcyclopropane；(2-Methyl-1,3-diphenylcyclopropyl)benzene
• CAS: 130138-97-5
• 化学式: C₂₂H₂₀
• 分子量: 284.401
• InChiKey: DVFUCBZFIMICCM-UHFFFAOYSA-N

物化性质

• 沸点：
  377.4±42.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  反式-1,1,1-三苯基-2-丁烯 生成 1,1,2-triphenyl-3-methylcyclopropane
  参考文献：
  名称：

  SHI, MIN;OKAMOTO, YOSHIKI;TAKAMUKU, SETSUO, CHEM. LETT.,(1990) N, C. 1079-1082

  摘要：

  DOI：

文献信息

• Photolysis of 1,1,1-Triphenyl-2-alkenes and Methyl Triphenylacetate
  作者：Min Shi、Yoshiki Okamoto、Setsuo Takamuku

  DOI：10.1246/cl.1990.1079

  日期：1990.7

  in methanol 1,1,1-triphenyl-2-alkene or methyl triphenylacetate underwent two kinds of α,α-elimination of two phenyl groups and phenyl-alkenyl groups or phenyl-methoxycarbonyl groups to give biphenyl, 1-phenylalkene or methyl benzoate, and two kinds of corresponding carbene intermediates, which inserted into the O–H bond of methanol to afford two kinds of methyl ethers, respectively.

  在甲醇中紫外线照射后，1,1,1-三苯基-2-烯烃或三苯基乙酸甲酯经历了两个苯基和苯基-烯基或苯基-甲氧基羰基的两种α,α-消除，得到联苯、1-苯基烯烃或苯甲酸甲酯和两种相应的卡宾中间体，插入甲醇的 O-H 键，分别得到两种甲基醚。
• Isolation and X-ray Crystal Structure of an Unusual Biscarbene Metal Complex and Its Reactivity toward Cyclopropanation and Allylic C−H Insertion of Unfunctionalized Alkenes
  作者：Yan Li、Jie-Sheng Huang、Zhong-Yuan Zhou、Chi-Ming Che

  DOI：10.1021/ja003184q

  日期：2001.5.1
• Shi, Min; Shouki, Kouji; Okamoto, Yoshiki, Journal of the Chemical Society. Perkin transactions I, 1990, # 9, p. 2443 - 2450
  作者：Shi, Min、Shouki, Kouji、Okamoto, Yoshiki、Takamuku, Setsuo

  DOI：——

  日期：——
• Discrete Bridging and Terminal Copper Carbenes in Copper-Catalyzed Cyclopropanation
  作者：Xuliang Dai、Timothy H. Warren

  DOI：10.1021/ja047935q

  日期：2004.8.1

  The Cu(I) beta-diketiminate [Me2NN]Cu(eta(2)-ethylene) (2) catalyzes the cyclopropanation of styrene with N2CPh2 to give 1,1,2-triphenylcyclopropane in 67% yield. Addition of N2CPh2 to 2 equiv of 2 allows for the isolation of the dicopper carbene [Me2NN]Cu}(2)(mu-CPh2) (3) in which the diphenylcarbene moiety is symmetrically bound between two [Me2NN]Cu fragments (Cu-C = 1.922(4) and 1.930(4) Angstrom) with a Cu-Cu separation of 2.4635(7) Angstrom. In toluene-d(8) solution, 3 reversibly dissociates a [Me2NN]Cu fragment to give [Me2NN]Cu(toluene) and the terminal carbene [Me2NN]Cu=CPh2. Dicopper carbene 3 reacts with 3 equiv of styrene to give 1,1,2-triphenylcyclopropane and 2 equiv of [Me2NN]Cu(eta(2)-styrene) within minutes. DFT studies with simplified ligands indicate a stronger Cu-C pi-back-bonding interaction from two Cu(I) centers to the carbene acceptor orbital in a dicopper carbene than that present in a monocopper carbene. Nonetheless, the terminal carbene [Me3NN]Cu=CPh2 (8) that possesses a p-methyl group on each beta-diketiminato N-aryl ring may be isolated and exhibits a shortened Cu-C distance of 1.834(3) Angstrom. The stoichiometric cyclopropanation of styrene by 8 in 1,4-dioxane is first-order in both copper carbene 8 and styrene with activation parameters DeltaH(not similar or equal to) = 10.4(3) kcal/mol and DeltaS(not similar or equal to) = -32.3(9) cal/mol-K. In 1,4-dioxane, 8 decomposes to Ph2C=CPh2 via first-order kinetics with activation parameters DeltaH(not similar or equal to) = 21(1) kcal/mol and DeltaS(not similar or equal to) = -8(3) cal/mol-K. Arene solutions of thermally sensitive terminal carbene 8 decompose to [Me3NN]-Cu(arene), which reacts with 8 still present in solution to give the more thermally stable [Me3NN]Cu}(2)-(mu-CPh2).
• SHI, MIN;SHOUKI, KOUJI;OKAMOTO, YOSHIKI;TAKAMUKU, SETSUO, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 2443-2450
  作者：SHI, MIN、SHOUKI, KOUJI、OKAMOTO, YOSHIKI、TAKAMUKU, SETSUO

  DOI：——

  日期：——