3-ethyl-1-methyl-1H-indene | 26084-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 3-ethyl-1-methyl-1H-indene
• 英文别名: 3-ethyl-1-methylindene；rac. 1-Methyl-3-ethyl-inden；1-Methyl-3-ethylinden
• CAS: 26084-58-2
• 化学式: C₁₂H₁₄
• 分子量: 158.243
• InChiKey: NWMHWOUIHYPGFP-UHFFFAOYSA-N

物化性质

• 沸点：
  93-94 °C(Press: 9 Torr)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-ethyl-1-methyl-1H-indene 、 (1-methyl-2,3-diphenylcycloprop-2-en-1-yl) perchlorate 以8%的产率得到
  参考文献：
  名称：

  PADWA, ALBERT;CORDOVA, DIANA M.;PULWER, MITCHELL J., J. ORG. CHEM., 56,(1991) N5, C. 4747-4753

  摘要：

  DOI：
• 作为产物：
  描述：

  2-ethyl-3-methyl-1H-indene 生成 3-ethyl-1-methyl-1H-indene
  参考文献：
  名称：

  MORRISON, H.;GIACHERIO, D.;PALENSKY, F. J., J. ORG. CHEM., 1982, 47, N 6, 1051-1058

  摘要：

  DOI：

文献信息

• A Gold(I)-Catalyzed Domino Coupling of Alcohols with Allenes Enables the Synthesis of Highly Substituted Indenes
  作者：Alexander Preinfalk、Antonio Misale、Nuno Maulide

  DOI：10.1002/chem.201603154

  日期：2016.10.4

  The reaction of aryl‐substituted allenes with alcohols under gold catalysis led to highly substituted indenes in good yields, with low catalyst loading and under mild conditions. During this domino transformation, two C−C bonds are formed with water as the only byproduct.

  在金催化下，芳基取代的烯与醇的反应导致高取代度的茚满，收率高，催化剂用量低，且条件温和。在此多米诺骨牌转化过程中，两个CC键与水形成了唯一的副产物。
• Organic photochemistry. 50. Photoinduced skeletal rearrangement of alkylindenes
  作者：Harry Morrison、David Giacherio、Frederick J. Balensky

  DOI：10.1021/jo00345a031

  日期：1982.3
• Meurling,L., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1974, vol. 28, p. 295 - 300
  作者：Meurling,L.

  DOI：——

  日期：——
• Studies dealing with cycloaddition and sigmatropic reactions of cyclopropenyl-substituted indenes
  作者：Albert Padwa、Diana M. Cordova、Mitchell J. Pulwer

  DOI：10.1021/jo00015a033

  日期：1991.7

  The thermal and photochemical reactions of a number of substituted cyclopropenylindenes have been studied. The thermolysis of these systems resulted in a series of 3,3-sigmatropic rearrangements. The product distribution parallels the expected relative order of thermodynamic stabilities of the indenes. The major product obtained upon extended heating corresponds to the isomer in which the double bonds are in conjugation with the phenyl groups on both the indene and cyclopropene rings. Direct irradiation of 1-methyl-1-(1-methyl-2,3-diphenyl-2-cyclopropen-1-yl)-3-phenylindene afforded a mixture of unsymmetrical cyclopropenes together with a cyclopropa[cd]pentalene. The formation of the products can be rationalized in terms of two competing pathways. One path involves sigma-bond cleavage to produce a diradical pair which undergoes recombination to give the rearranged cyclopropene. The alternate pathway proceeds by ring opening of the singlet state of the cyclopropene to a vinylcarbene intermediate. Attack of the vinylcarbene carbon on the neighboring double bond produces the cyclopropa[cd]pentalene ring skeleton. The sensitized photolysis was found to give intramolecular [2 + 2]-cycloadducts. The observed regiospecificity of the reaction is understandable in terms of formation of the most stable diradical intermediate.