1-trimethylsilyl-2-methylindene | 58295-07-1

• 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-trimethylsilyl-2-methylindene
• 英文别名: trimethyl (2-methyl-1H-inden-3-yl) silane；1-Trimethylsilyl-2-methylinden；trimethyl-(2-methyl-3H-inden-1-yl)silane
• CAS: 58295-07-1
• 化学式: C₁₃H₁₈Si
• 分子量: 202.371
• InChiKey: QAVVYIQDVXAXET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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-trimethylsilyl-2-methylindene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以83 %的产率得到
  参考文献：
  名称：

  通过钌催化的醛基和酰基硅烷的 C-H 烷基化/环化合成甲硅烷基茚

  摘要：

  提出了一种钌催化的 C–H 烷基化/环化序列，以原子和步骤经济的方式制备甲硅烷基茚。这种多米诺骨牌反应是由酰基硅烷引导的 C-H 活化引发的，醛控制着随后的烯醇环化/缩合，而不是 β-H 消除。该方案允许广泛的取代模式，并且甲硅烷基茚的进一步合成精制允许获得各种有趣的茚和茚满酮衍生物。

  DOI：

  10.1039/d3ob01699d
• 作为产物：
  描述：

  2-茚酮 在 正丁基锂 、 对甲苯磺酸 作用下， 以 正己烷 为溶剂， 反应 4.0h， 生成 1-trimethylsilyl-2-methylindene
  参考文献：
  名称：

  Alkyl-substituted indenyl titanium precursors for syndiospecific ziegler-natta polymerization of styrene

  摘要：

  A variety of 1- and 3-substituted alkylindenes (R = H, Me, Et, tert-butyl, Me(3)Si) as well as 2-methylindene and 3-(methylthio)indene have been prepared in good yields. The substituted indenes were converted into trimethylsilyl derivatives via reactions of intermediate organolithium complexes with chlorotrimethylsilane. The corresponding titanium complexes, (R-Ind)TiCl3, were synthesized in excellent yield from reactions of the trimethylsilyl derivatives with TiCl4. The titanium complexes were evaluated as styrene polymerization catalysts in toluene solution when activated by methylaluminoxane. Activities increased in the order: Cp < H(4)Ind < Ind < 1-(Me)Ind < 2-(Me)Ind. A steep drop in activity was observed when R = Et, tert-butyl, and Me(3)Si, corresponding to an increase in the steric bulk of the substituent in the catalyst precursor. 1-(MeS)IndTiCl(3) was found to be ineffective as a styrene polymerization catalyst. Syndiospecificities of the titanium complexes were generally very good (65-98%).

  DOI：

  10.1016/s0022-328x(96)06153-0

文献信息

• Rh(I)-Catalyzed Reaction of 2-(Chloromethyl)phenylboronic Acids and Alkynes Leading to Indenes
  作者：Masaki Miyamoto、Yasuyuki Harada、Mamoru Tobisu、Naoto Chatani

  DOI：10.1021/ol8006887

  日期：2008.7.17

  The reaction of 2-(chloromethyl)phenylboronic acid (1) with alkynes in the presence of a Rh(I) complex gave indene derivatives in high yields. The regioselectivity depends on the steric nature of the substituent on the alkynes. A bulky group favors the alpha-position of indenes.
• Alkyl-substituted indenyl titanium precursors for syndiospecific ziegler-natta polymerization of styrene
  作者：Thomas E. Ready、James C.W. Chien、Marvin D. Rausch

  DOI：10.1016/s0022-328x(96)06153-0

  日期：1996.7

  A variety of 1- and 3-substituted alkylindenes (R = H, Me, Et, tert-butyl, Me(3)Si) as well as 2-methylindene and 3-(methylthio)indene have been prepared in good yields. The substituted indenes were converted into trimethylsilyl derivatives via reactions of intermediate organolithium complexes with chlorotrimethylsilane. The corresponding titanium complexes, (R-Ind)TiCl3, were synthesized in excellent yield from reactions of the trimethylsilyl derivatives with TiCl4. The titanium complexes were evaluated as styrene polymerization catalysts in toluene solution when activated by methylaluminoxane. Activities increased in the order: Cp < H(4)Ind < Ind < 1-(Me)Ind < 2-(Me)Ind. A steep drop in activity was observed when R = Et, tert-butyl, and Me(3)Si, corresponding to an increase in the steric bulk of the substituent in the catalyst precursor. 1-(MeS)IndTiCl(3) was found to be ineffective as a styrene polymerization catalyst. Syndiospecificities of the titanium complexes were generally very good (65-98%).
• Synthesis of silyl indenes by ruthenium-catalyzed aldehyde- and acylsilane-enabled C–H alkylation/cyclization
  作者：Tao Zhang、Cheng Zhang、Xiunan Lu、Chengxing Peng、Yawei Zhang、Xiong Zhu、Guofu Zhong、Jian Zhang

  DOI：10.1039/d3ob01699d

  日期：——

  A ruthenium-catalyzed C–H alkylation/cyclization sequence is presented to prepare silyl indenes with atom and step-economy. This domino reaction is triggered by acyl silane-directed C–H activation, and an aldehyde controlled the following enol cyclization/condensation other than β-H elimination. The protocol tolerates a broad substitution pattern, and the further synthetic elaboration of silyl indenes

  提出了一种钌催化的 C–H 烷基化/环化序列，以原子和步骤经济的方式制备甲硅烷基茚。这种多米诺骨牌反应是由酰基硅烷引导的 C-H 活化引发的，醛控制着随后的烯醇环化/缩合，而不是 β-H 消除。该方案允许广泛的取代模式，并且甲硅烷基茚的进一步合成精制允许获得各种有趣的茚和茚满酮衍生物。