2,2-Dimethyl-1-methyleneindan | 134261-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2,2-Dimethyl-1-methyleneindan
• 英文别名: 2,2-dimethyl-1-methylideneindane；2,2-dimethyl-3-methylidene-1H-indene
• CAS: 134261-70-4
• 化学式: C₁₂H₁₄
• 分子量: 158.243
• InChiKey: BDGDXCMINMAJTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  0
• 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：

  2,2-Dimethyl-1-methyleneindan 在 (η⁴-1,5-cyclooctadiene) [(Sp)-1-[(1R)-(1-(5-methoxy-3H-isobenzofuran-1-ylideneamino)-ethyl)]-2-(diphenylphosphino)ferrocene]iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以40%的产率得到
  参考文献：
  名称：

  Chiral imidate–ferrocenylphosphanes: synthesis and application as P,N-ligands in iridium(i)-catalyzed hydrogenation of unfunctionalized and poorly functionalized olefins

  摘要：

  高效合成了一小类手性咪唑酰亚胺–铁烯基膦配体（8个例子），并在铱(I)催化的未功能化和功能化较差的烯烃的加氢反应中进行了评估。这些催化剂在一系列的例子中表现非常良好（产率和对映体过量高达100%）。

  DOI：

  10.1039/c2ob25871d
• 作为产物：
  描述：

  在 bis-triphenylphosphine-palladium(II) chloride 、 silver trifluoromethanesulfonate 、 三乙胺 作用下， 以 氘代四氢呋喃 为溶剂， 以84%的产率得到2,2-Dimethyl-1-methyleneindan
  参考文献：
  名称：

  在有机金Heck反应中直接观察金/钯的金属转移

  摘要：

  一种新的Heck型反应从有机金络合物中获得了钯的迁移插入化学。钯中间体的观察，分离和表征确立了金/钯金属转移在该反应中的作用。尽管有机金化合物与钯的反应性在有机合成中的结合的最新报道通常假定金-钯的过渡金属化步骤，尽管在这些反应中没有直接观察到该步骤。本文的结果为由金和钯两者介导或催化的反应机理提供了实验证据，并揭示了克服同质耦合途径的迁移插入策略。

  DOI：

  10.1021/om2006886

文献信息

• Nickel-catalyzed olefination of cyclic benzylic dithioacetals by Grignard reagents. Scope and mechanism
  作者：Zhi Jie Ni、Nai Wen Mei、Xian Shi、Yih Ling Tzeng、Maw Cherng Wang、Tien Yau Luh

  DOI：10.1021/jo00012a043

  日期：1991.6

  The details of the first nickel-catalyzed olefination of cyclic dithioacetals to form substituted styrenes and aryl-substituted 1,4-pentadienes are described. The reaction represents a new synthetic use of the dithioacetal functionality. Only nickel complexes catalyzed these cross-coupling reactions; palladium complexes displayed no catalytic activity under the reaction conditions employed. Selective coupling occurred. A mechanism for the reaction is proposed. The experimental evidence indicates that, in these nickel-catalyzed couplings, cyclic dithioacetals are more reactive than their acyclic analogues. This increased reactivity appears to be the result of maintaining the two sulfur atoms in close proximity to each other by the use of a short chain of methylene groups.
• Diethylaluminum Chloride Mediated Vinylsilane Synthesis: Comparison of Different Solvent Systems
  作者：Man Lung Kwan、Merle A. Battiste、Megan K. Macala、Sylvia C. Aybar、Nicholas C. James、Joseph J. Haoui

  DOI：10.1081/scc-120037906

  日期：2004.12.31

  Aromatic ketones were converted to one-carbon elongated-vinylsilanes in a convenient one-pot operation via the Peterson protocol. Reactions were conducted in two different solvents for comparison: pentane and triethylamine. Results indicate that triethylamine appeared to be a more suitable solvent for such a transformation producing vinylsilanes with great chemo- and stereo-selectivity than pentane.
• Chiral imidate–ferrocenylphosphanes: synthesis and application as P,N-ligands in iridium(i)-catalyzed hydrogenation of unfunctionalized and poorly functionalized olefins
  作者：Katrien Bert、Timothy Noël、Wim Kimpe、Jan L. Goeman、Johan Van der Eycken

  DOI：10.1039/c2ob25871d

  日期：——

  A small library of chiral imidate–ferrocenylphosphane ligands was efficiently synthesized (8 examples) and evaluated in the iridium(I)-catalyzed hydrogenation of unfunctionalized and poorly functionalized olefins. These catalysts perform very well in a range of examples (yields and ee's up to 100%).

  高效合成了一小类手性咪唑酰亚胺–铁烯基膦配体（8个例子），并在铱(I)催化的未功能化和功能化较差的烯烃的加氢反应中进行了评估。这些催化剂在一系列的例子中表现非常良好（产率和对映体过量高达100%）。
• Direct Observation of Gold/Palladium Transmetalation in an Organogold Heck Reaction
  作者：Katrina E. Roth、Suzanne A. Blum

  DOI：10.1021/om2006886

  日期：2011.9.26

  Observation, isolation, and characterization of a palladium intermediate established the role of gold/palladium transmetalation in this reaction. Recent reports of combining the reactivity of organogold compounds with palladium in organic synthesis generally assume a gold-to-palladium transmetalation step, although this step had not been directly observed in these reactions. The results herein furnish

  一种新的Heck型反应从有机金络合物中获得了钯的迁移插入化学。钯中间体的观察，分离和表征确立了金/钯金属转移在该反应中的作用。尽管有机金化合物与钯的反应性在有机合成中的结合的最新报道通常假定金-钯的过渡金属化步骤，尽管在这些反应中没有直接观察到该步骤。本文的结果为由金和钯两者介导或催化的反应机理提供了实验证据，并揭示了克服同质耦合途径的迁移插入策略。