6-methyl-6-cyclopropylfulvene | 61010-59-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 6-methyl-6-cyclopropylfulvene
• 英文别名: 6-Cyclopropyl-6-methylfulvene；5-(1-Cyclopropylethylidene)cyclopenta-1,3-diene
• CAS: 61010-59-1
• 化学式: C₁₀H₁₂
• 分子量: 132.205
• InChiKey: XGLPXHRXEBCEPX-UHFFFAOYSA-N

物化性质

• 沸点：
  204.8±7.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  6-methyl-6-cyclopropylfulvene 生成 7-Methyl-4,5-dihydro-2H-indene
  参考文献：
  名称：

  GRIESBECK, AXEL G.;PERETRS, KARL;PETERS, EVA-MARIA;SCHNERING, HANS GEORG, ANGEW. CHEM., 102,(1990) N, C. 801-803

  摘要：

  DOI：
• 作为产物：
  描述：

  环丙甲基酮 、 环戊二烯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 6-methyl-6-cyclopropylfulvene
  参考文献：
  名称：

  Stable carbocations. 203. Proton and carbon-13 nuclear magnetic resonance spectroscopic study of 6,6-disubstituted fulvenium ions

  摘要：

  DOI：

  10.1021/jo00424a018

文献信息

• Aluminum carbenoids in the cyclopropanation of fulvenes
  作者：I. R. Ramazanov、A. V. Yaroslavova、N. R. Yaubasarov、U. M. Dzhemilev

  DOI：10.1007/s11172-018-2096-5

  日期：2018.3

  Et2AlCH2I reacts with 6-substituted fulvenes to give tricyclopropanes in high yields. Calculations at the B3LYP/6-31G(d) level of theory show that coplanar arrangement of the double bonds facilitates cyclopropanation due to conjugation in the transition state. Aluminum carbenoid Et2AlCH2I was generated by either the reaction of equimolar amounts of Et3Al and CH2I2 in hexane or treatment of Et2AlI with CH2N2

  铝碳烯 Et2AlCH2I 与 6-取代的富烯反应以高产率得到三环丙烷。B3LYP/6-31G(d) 理论水平的计算表明，由于在过渡态共轭，双键的共面排列促进了环丙烷化。通过等摩尔量的 Et3Al 和 CH2I2 在己烷中的反应或在二氯甲烷中用 CH2N2 处理 Et2AlI，生成铝碳化物 Et2AlCH2I。
• Dimethyldioxirane epoxidation of 6,6-disubstituted fulvenes.
  作者：Waldemar Adam、Lazaros P. Hadjiarapoglou、Anja Meffert

  DOI：10.1016/s0040-4039(00)93578-0

  日期：1991.11

  The endocyclic bis-epoxides of various pentafulvenes were readily prepared by epoxidation with excess dimethyldioxirane; stoichiometric epoxidation yielded mixtures of the bis-epoxides and the labile mono-epoxides, but no exocyclic epoxides were observed.

  可以通过用过量的二甲基二环氧乙烷进行环氧化来轻松制得各种五氟戊烯的内环双环氧化物。化学计量的环氧化产生双环氧化物和不稳定的单环氧化物的混合物，但未观察到环外环氧化物。
• Cyclopropylcarbinyl ring opening as mechanistic probe for differentiation between the singlet and triplet spin states of trimethylenemethane diradicals (non-Kekule species)
  作者：Waldemar Adam、Ralf Finzel

  DOI：10.1021/ja00038a018

  日期：1992.6

  The cyclopropylcarbinyl rearrangement of the non-Kekule 2-alkylidene-1,3-cyclopentanediyl diradical (S-2b and T-2b), generated by thermal and direct and triplet-sensitized photochemical denitrogenation of the corresponding azoalkane 1b, was explored. While in the triplet-sensitized photolysis at moderate temperatures no cyclopropylcarbinyl rearrangement took place, in the singlet manifold (thermolysis

  探索了非 Kekule 2-亚烷基-1,3-环戊二基双自由基（S-2b 和 T-2b）的环丙基羰基重排，由相应的偶氮烷 1b 的热和直接和三线态敏化光化学脱氮产生。虽然在中等温度下的三线态敏化光解中没有发生环丙基羰基重排，但在单线态歧管（热解和直接光解）中观察到重排的烃 3。重排烃 3 的量随着温度的升高而增加，并且从温度依赖性来看，活化能约为 开环估计为 5 kcal/mol
• Reaction of diazoalkanes with unsaturated compounds. Communication 2. Cyclopropanation of olefins by diazomethane in the presence of palladium compounds
  作者：Yu. V. Tomilov、V. G. Bordakov、I. E. Dolgii、O. M. Nefedov

  DOI：10.1007/bf00995691

  日期：1984.3
• Sulfur ylides. 4. Cyclopropanation of fulvenes by ethyl (dimethylsulfuranylidene)acetate under interphase catalysis conditions
  作者：G. A. Tolstikov、F. Z. Galin、V. N. Iskandarova、S. N. Lakeev、L. V. Spirikhin、L. M. Khalilov

  DOI：10.1007/bf00962390

  日期：1990.6

  The reaction was studied of fulvenes with ethyl (dimethylsulfuranylidene)acetate generated under interphase catalysis conditions from the sulfonium salt [MeS+CH2-CO2Et)]Br- by the action of 85% KOH in the presence of triethylbenzylammonium chloride.