3-cyclohexylindene | 138036-91-6

• 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-cyclohexylindene
• 英文别名: 3-cyclohexyl-1H-indene
• CAS: 138036-91-6
• 化学式: C₁₅H₁₈
• 分子量: 198.308
• InChiKey: SKMDXHGONCSUIO-UHFFFAOYSA-N

物化性质

• 沸点：
  311.0±17.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 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-cyclohexylindene 在 sodium amide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以95.2%的产率得到sodium 1-(cyclohexyl)indenide
  参考文献：
  名称：

  How big is a Cp? Cycloheptatrienyl zirconium complexes with bulky cyclopentadienyl and indenyl ligands

  摘要：

  采用相转移和传统烷基化策略的结合，合成了空间位阻较大的1,3-二(环己基)和1,3-二(叔丁基)取代的茚，并且产量达到数克。这些茚基配体和空间位阻较大的烷基环戊二烯基配体用于通过简单的盐交换反应，制备一系列[(η7-C7H7)Zr(η5-L)]（L = Cp 和 Ind）配合物，反应物为[(η7-C7H7)ZrCl(tmeda)]与相应的钠茚化物或环戊二烯化物。所有这些锆配合物都通过元素分析、核磁共振光谱和单晶X射线衍射进行了表征。这些研究获得的结构信息被用于以现实的方式评估这些配体的空间需求。

  DOI：

  10.1039/c2dt12132h
• 作为产物：
  描述：

  溴代环己烷 、 茚 在 potassium hydroxide 作用下， 以 水 为溶剂， 以72%的产率得到3-cyclohexylindene
  参考文献：
  名称：

  How big is a Cp? Cycloheptatrienyl zirconium complexes with bulky cyclopentadienyl and indenyl ligands

  摘要：

  采用相转移和传统烷基化策略的结合，合成了空间位阻较大的1,3-二(环己基)和1,3-二(叔丁基)取代的茚，并且产量达到数克。这些茚基配体和空间位阻较大的烷基环戊二烯基配体用于通过简单的盐交换反应，制备一系列[(η7-C7H7)Zr(η5-L)]（L = Cp 和 Ind）配合物，反应物为[(η7-C7H7)ZrCl(tmeda)]与相应的钠茚化物或环戊二烯化物。所有这些锆配合物都通过元素分析、核磁共振光谱和单晶X射线衍射进行了表征。这些研究获得的结构信息被用于以现实的方式评估这些配体的空间需求。

  DOI：

  10.1039/c2dt12132h

文献信息

• Facile Benzylic Alkylation of Arenes with Alcohols by Catalysis with Spirocyclic NHC Ir ^III Pincer Complex
  作者：Kun‐Long Dai、Qi‐Long Chen、Wen‐Ping Xie、Ka Lu、Zhi‐Bo Yan、Meng Peng、Chang‐Kun Li、Yong‐Qiang Tu、Tong‐Mei Ding

  DOI：10.1002/anie.202206446

  日期：2022.9.19

  A facile IrIII-catalyzed benzylic alkylation of arenes with alcohols has been accomplished via borrowing hydrogen (BH) pathways, and the newly developed spirocyclic NHC IrIII pincer complex (Cat A) serves as an efficient catalyst for this atom-economical and greener transformation. Some drug or bioactive molecules and functional material templates can be easily constructed by this strategy.

  通过借氢 (BH) 途径实现了一种简单的 Ir III催化的芳烃与醇的苄基烷基化，新开发的螺环 NHC Ir III钳形配合物 (Cat A) 可作为这种原子经济和绿色转化的有效催化剂. 一些药物或生物活性分子和功能材料模板可以通过这种策略轻松构建。
• 10.1021/acs.orglett.4c01400
  作者：Perez, Alma R.、Hanks, Garret T.、Bornowski, Evan C.、Wolfe, John P.

  DOI：10.1021/acs.orglett.4c01400

  日期：——

  The palladium-catalyzed cross-coupling of 2-allylphenyl triflate and related electrophiles with substituted indenes affords biindene derivatives in moderate to good yields with high selectivity for thermodynamically preferred alkene isomers. The transformations involve alkene nucleopalladation with indenyl anions, and we also demonstrate that 2-allylphenyl triflates can be transformed to indenes under

  2-烯丙基苯基三氟甲磺酸酯和相关亲电子试剂与取代茚的钯催化交叉偶联以中等至良好的产率提供联茚衍生物，并且对热力学优选的烯烃异构体具有高选择性。该转化涉及烯烃与茚基阴离子的核钯化，我们还证明了 2-烯丙基苯基三氟甲磺酸酯可以在类似条件下转化为茚。描述了这种转化的范围以及茚和联茚产物的形成机制。
• Ethylene-bridged C1-symmetric ansa-(3-R-indenyl)(fluorenyl) zirconocene complexes for propylene dimerization or polymerization: The effect of R group
  作者：Yan Wang、Wenzhong Huang、Haiyan Ma、Jiling Huang

  DOI：10.1016/j.poly.2014.03.019

  日期：2014.7

  A series of ethylene-bridged C-1-symmetric ansa-(3-R-indenyl)(fluorenyl) zirconocene complexes 3a-i (R = 2[2-(4-methylphenyl)propyl], 3a; R = 2-[2-(3,5-dimethylphenyl)propyl], 3h; R = 2-(2-benzylpropyl), 3c; R = 2-methylbenzyl, 3d; R = 2-(2-cyclohexylpropyl), 3e; R = 2-[2-(1-cyclohexenyl)propyl], 3f; R = 2-(2-n-butylpropyl), 3g; R = cyclohexyl, 3h; R = Pr-i, 3i) were synthesized by a salt metathesis method and characterized by NMR spectroscopy, elemental analysis (or HRMS) and X-ray diffraction (3e and 3h). Upon activation with methylaluminoxane, most of these zirconocene complexes exhibited sufficient catalytic activities up to 2.5 x 10(5) g C-6/(mol-Zr.h) and high selectivities up to 99% toward propylene dimerization, affording 2-methyl-1-pentene as the major isomer which was confirmed by gas chromatography. Remarkably, the selectivity and activity of complexes 3a-i were significantly influenced by the structural features of the substituent on the 3-position of indenyl ring: a pendant aryl or alkyl group linked by a quaternary carbon bridge provided the complex with high selectivities in the range of 89.9-99.0% for 2-methyl-1-pentene and low to moderate catalytic activities; the lack of a quaternary carbon bridge within the substituent would lead to mainly polypropylenes of low molecular weight. The steric hindrance around the active metal center induced by the pendant group might be responsible for the catalytic dimerization behavior, and the presumed mechanism was discussed. In addition, for complexes 3h and 3i, the selectivity for propylene dimerization could also be enhanced with the increase of reaction temperature. Noticeably, most of these ansa-zirconocene complexes exhibit excellent thermal stability at 100 degrees C, which is important with regard to industrial application. (C) 2014 Elsevier Ltd. All rights reserved.
• Phase transfer catalyzed tert-alkylations of cyclopentadiene and indene: indications for set processes
  作者：Eckehard V. Dehmlow、Christof Bollmann

  DOI：10.1016/s0040-4039(00)93552-4

  日期：1991.10

  Scope and mechanism of the PTC tert-alkylation of cyclopentadienide anion have been investigated. On the side of the anion, the reaction is limited to cyclopentadiene and indene, whereas many tertiary as well as secondary and primary alkylating agents can be employed. Hexamethylcyclopentadiene 8, for instance, is available easily. Tert-alkylations of this type are more effective if 4,4'-bipyridinium salts are present in addition to a phase transfer catalyst. The reactions involve probably an initial single electron transfer (SET) step.
• How big is a Cp? Cycloheptatrienyl zirconium complexes with bulky cyclopentadienyl and indenyl ligands
  作者：Andreas Glöckner、Heiko Bauer、Miyuki Maekawa、Thomas Bannenberg、Constantin G. Daniliuc、Peter G. Jones、Yu Sun、Helmut Sitzmann、Matthias Tamm、Marc D. Walter

  DOI：10.1039/c2dt12132h

  日期：——

  A combination of phase-transfer and traditional alkylation strategies has been employed to synthesise sterically encumbered 1,3-di(cyclohexyl) and 1,3-di(tert-butyl) substituted indenes in multi-gram quantities. These indenyl ligands and sterically demanding alkyl cyclopentadienyl ligands have been used to prepare a series of [(η7-C7H7)Zr(η5-L)] (L = Cp and Ind) complexes by straightforward salt metathesis between [(η7-C7H7)ZrCl(tmeda)] and the corresponding sodium indenide or cyclopentadienide. All of these Zr complexes have been characterized by elemental analysis, NMR spectroscopy and single crystal X-ray diffraction. The structural information derived from these studies was employed to evaluate the steric demand of these ligands in a realistic manner.

  采用相转移和传统烷基化策略的结合，合成了空间位阻较大的1,3-二(环己基)和1,3-二(叔丁基)取代的茚，并且产量达到数克。这些茚基配体和空间位阻较大的烷基环戊二烯基配体用于通过简单的盐交换反应，制备一系列[(η7-C7H7)Zr(η5-L)]（L = Cp 和 Ind）配合物，反应物为[(η7-C7H7)ZrCl(tmeda)]与相应的钠茚化物或环戊二烯化物。所有这些锆配合物都通过元素分析、核磁共振光谱和单晶X射线衍射进行了表征。这些研究获得的结构信息被用于以现实的方式评估这些配体的空间需求。