1-Methyl-3-phenylinden | 22360-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 1-Methyl-3-phenylinden
• 英文别名: 3-Methyl-1-phenyl-1H-indene
• CAS: 22360-63-0
• 化学式: C₁₆H₁₄
• 分子量: 206.287
• InChiKey: IDMJMCFZGJWXOE-UHFFFAOYSA-N

物化性质

• 熔点：
  65 °C
• 沸点：
  89-92 °C(Press: 0.04 Torr)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1-Methyl-3-phenylinden 在 正丁基锂 、 氘代甲醇-d 、 四甲基乙二胺 作用下， 生成 1-Deuterio-1-phenyl-3-methylindene
  参考文献：
  名称：

  Sigmatropic indenyl rearrangements induced by electronic excitation

  摘要：

  DOI：

  10.1021/jo00322a023
• 作为产物：
  描述：

  cis-2.4-Diphenyl-3-buten-2-ol 生成 1-Methyl-3-phenylinden
  参考文献：
  名称：

  Cationic cyclizations. Cation generation through magnesium alkoxide thermolysis. Regioselective indene formation

  摘要：

  DOI：

  10.1021/jo00393a027

文献信息

• The intramolecular reaction of acetophenone <i>N</i>-tosylhydrazone and vinyl: Brønsted acid-promoted cationic cyclization toward polysubstituted indenes
  作者：Zhixin Wang、Yang Li、Fan Chen、Peng-Cheng Qian、Jiang Cheng

  DOI：10.1039/d0cc07966a

  日期：——

  TsNHNH2, a Brønsted acid-promoted intramolecular cyclization of o-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydic N-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, where N-tosylhydrazone served

  在存在TsNHNH 2的情况下，开发了布朗斯台德酸促进的邻-（1-芳基乙烯基）苯乙酮衍生物的分子内环化反应，导致多取代的茚并酮具有复杂性和多样性，产率中等至优异。与自由基或卡宾涉及醛基N-甲苯磺酰hydr与乙烯基的环化形成鲜明对比，涉及阳离子环化途径，其中N-甲苯磺酰zone在该转化过程中用作亲电试剂和烷基化试剂。
• Palladium-catalyzed direct cross-coupling reaction between indenes and electron-deficient alkenes
  作者：Yun-He Xu、Wee-Jian Wang、Zhen-Kang Wen、Joshua Johnathan Hartley、Teck-Peng Loh

  DOI：10.1016/j.tetlet.2010.04.097

  日期：2010.7

  An efficient methodology for oxidative cross-coupling of indene and derivatives with electron-deficient olefins catalyzed by palladium was developed. The corresponding diene products were obtained in moderate to good yields.

  开发了一种有效的方法，用于钯催化的茚与衍生物与缺电子烯烃的氧化交联。以中等至良好的产率获得了相应的二烯产物。
• Indene and indane compounds and their production
  申请人：CIBA PHARM PROD INC

  公开号：US02798888A1

  公开（公告）日：1957-07-09
• Friedel-Crafts-type reactions involving di- and tricationic species. Onium-allyl dications and O,O-diprotonated aci-nitro species bearing a protonated carbonyl group
  作者：Tomohiko Ohwada、Naoko Yamagata、Koichi Shudo

  DOI：10.1021/ja00004a044

  日期：1991.2

  Stable carbocations do not react with nonactivated benzenes. For example, acetophenone does not react with benzene in the presence of trifluoromethanesulfonic acid (TFSA), while trifluoroacetophenone does do so under acidic conditions owing to activation of the electrophilicity of the hydroxycarbenium cation by the trifluoromethyl group. This and other studies suggest that an electron-withdrawing substituent on the cationic center increases the reactivity toward benzenes. In this paper, involvement of multiply positively charged (dicationic and tricationic) species, which have sufficient electrophilicity toward benzene, is demonstrated in the acid-catalyzed reactions of cinnamaldehyde and its derivatives and also in the acid-catalyzed reactions of nitromethanes. The species formed from cinnamaldehyde, cinnamaldimine, cinnamaldoxime, and their derivatives in TFSA or TFSA-SbF5 have an adequate reactivity toward benzene. O-Protonated cinnamaldehyde and its derivatives, N-protonated cinnamaldimine, and N,N-dimethylcinnamaldiminium salt do not react with benzene. Since a strong acid catalyst is required for the reactions, participation of doubly protonated species, onium-allyl dications, is proposed. Ab initio calculations of (1) the donor-acceptor interaction energies of a neutral donor (such as water and ammonia) and a doubly charged allyl dication and (2) proton affinities demonstrated that the ammonium-allyl dication is more stable than the oxonium-allyl dication, in accordance with the experimental observation. Nitronic acids also react with benzene at the ipso position with respect to the nitro group to give the phenylated oximes in the presence of TFSA. The reaction with benzene is not catalyzed by trifluoroacetic acid, which is sufficiently acidic to monoprotonate a nitronic acid to the protonated aci-nitro form. The reaction requires a stronger acid, trifluoromethanesulfonic acid, suggesting intervention of the dication formed by O,O-diprotonation of aci-nitroalkanes rather than the monoprotonated aci-nitroalkane. As a result of further study on the phenylation reactions, we found a facile phenylation reaction of nitromethanes substituted with an electron-withdrawing group, catalyzed by TFSA, to give phenylated alpha-carbonyloximes in high yields. A triply positively charged cation, an O,O-diprotonated aci-nitro species bearing a protonated ethoxycarbonyl group, which can react with nonactivated benzene, is proposed to be an intermediate in this reaction.
• Synthesis of the benzotricyclooctane ring system. Intramolecular [2 + 2] cycloaddition of indene derivatives
  作者：Albert Padwa、Steven Goldstein、Mitchell Pulwer

  DOI：10.1021/jo00141a018

  日期：1982.9