methyl 2-methylcyclohepta-2,4,6-triene-1-carboxylate | 75862-77-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-methylcyclohepta-2,4,6-triene-1-carboxylate
• 英文别名: 1-methyl 1,3,5-cycloheptatriene-7-carboxylate
• CAS: 75862-77-0
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: BPOGXERIIUVJTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲苯 、 重氮乙酸甲酯 、 rhodium(II) trifluoroacetate 以17%的产率得到
  参考文献：
  名称：

  ANCIAUX A. J.; DEMONCEAU A.; NOELS A. F.; HUBERT A. J.; WARIN R.; TEYSSIE+, J. ORG. CHEM., 1981, 46, NO 5, 873-876

  摘要：

  DOI：

文献信息

• Catalytic control of reactions of dipoles and carbenes; an easy and efficient synthesis of cycloheptatrienes from aromatic compounds by an extension of Buchner's reaction
  作者：André J. Anciaux、Albert Demonceau、André J. Hubert、Alfred F. Noels、Nicole Petiniot、Philippe Teyssié

  DOI：10.1039/c39800000765

  日期：——

  salts from strong carboxylic acids [particularly rhodium(II) trifluoroacetate] are novel and highly efficient catalysts for the preparation of substituted cycloheptatriene carboxylates from aromatic hydrocarbons and diazo-esters, and in contrast with the classical Buchner procedures these rhodium catalysts lead specifically to the 1-isomer (3), avoiding its subsequent prototropic conversion into conjugated

  由强羧酸[特别是三氟乙酸铑（II）铑]制成的新型高效催化剂，由芳烃和重氮酯制备取代的环庚三烯羧酸盐，与经典的布赫纳方法相反，这些铑催化剂特别导致了1-异构体（3），避免其随后的质子转化为共轭异构体。
• Transition-metal-catalyzed reactions of diazo compounds. 2. Addition to aromatic molecules: catalysis of Buchner's synthesis of cycloheptatrienes
  作者：A. J. Anciaux、A. Demonceau、A. F. Noels、A. J. Hubert、R. Warin、P. Teyssie

  DOI：10.1021/jo00318a010

  日期：1981.2
• A fluorous phase approach to rhodium-catalyzed carbenoid reactions with diazoacetates
  作者：Andreas Endres、Gerhard Maas

  DOI：10.1016/s0040-4039(99)01332-5

  日期：1999.8

  The cyclopropanation of alkenes with methyl diazoacetate in dichloromethane was catalyzed by rhodium(II) carboxylates containing a perfluoralkyl chain (Rh2L4, L = OOCC7F15 and OOC-C6H4-4-C6F13) The catalysts could be extracted into perfluoro(methylcyclohexane) and were reused several times without significant loss of activity. The same catalysts were used to achieve carbene transfer to toluene in the solvent system toluene-perfluoro(methylcyclohexane) at 60 degrees C. (C) 1999 Elsevier Science Ltd. All rights reserved.