1,1,4-trimethyl-2,3-dihydro-1H-indene | 16204-72-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1,1,4-trimethyl-2,3-dihydro-1H-indene
• 英文别名: 2,3-dihydro-1,1,4-trimethyl-1H-indene；1,1,4-trimethylindane；1,1,4-Trimethyl-indan；1,1,4-Trimethylindan；1H-Indene, 2,3-dihydro-1,1,4-trimethyl-；3,3,7-trimethyl-1,2-dihydroindene
• CAS: 16204-72-1
• 化学式: C₁₂H₁₆
• 分子量: 160.259
• InChiKey: USZSMCUXEWREKR-UHFFFAOYSA-N

物化性质

• 沸点：
  48 °C(Press: 0.7 Torr)
• 密度：
  0.9179 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1,1,4-trimethyl-2,3-dihydro-1H-indene 在 甲醇 、 platinum on activated charcoal 、 三氯化铝 、 1,2-二氯乙烷 、 palladium dichloride 作用下， 生成 6-ethyl-1,1,4-trimethyl-indan
  参考文献：
  名称：

  Odeur等人，第十八章。南苏丹的印度舞曲

  摘要：

  （1）本文描述了1,1-二甲基-4-乙酰基-6-叔丁基-茚满的合成，特别是我们对这种非常强的麝香化合物的结构研究，该化合物由MGJ甜菜和他的同事以及作者。

  DOI：

  10.1002/hlca.19590420640
• 作为产物：
  描述：

  2-bromo-1-(tert-butyl)-3-methylbenzene 在 正丁基锂 、 1,3‐bis[2,6‐bis(propan‐2‐yl)phenyl]‐2‐[(phenylformonitrile)aurio]‐2,3‐dihydro‐1H‐imidazol‐2‐yl hexafluorostibane 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 19.5h， 生成 1,1,4-trimethyl-2,3-dihydro-1H-indene
  参考文献：
  名称：

  通过环庚三烯的脱碳作用金（I）-催化的分子内C（sp3）-H插入

  摘要：

  基于分子内插入由逆布氏反应（脱碳）生成的金（I）碳烯的C（sp 3）-H键的新颖合成茚满和二氢萘烷的方法。氘标记和动力学同位素效应实验，DFT计算以及从特征明确的金（I）类胡萝卜素生成拟议的卡宾中间体均支持C（sp 3）-H功能化过程涉及三中心协同机制。

  DOI：

  10.1002/chem.201900919

文献信息

• Selective sp3 C-H Bond Activation Based on a Carbocation Relay: Friedel-Crafts Reaction with Alkanes as the Alkylating Component
  作者：Jie Wang、Pengfei Zhou、Yang Wang

  DOI：10.1002/ejoc.201001118

  日期：2011.1

  4-methylpentyl-substituted aromatics has been developed using a carbocation relay strategy through selective sp 3 C-H bond activation, providing a facile and cost-effective approach for the construction of benzocyclic compounds. A variety of 1,1-dimethylindane and naphthalene derivatives have been prepared from very simple starting materials in good yields with high selectivity. The present strategy

  使用碳阳离子中继策略通过选择性 sp 3 CH 键活化开发了一种高效且选择性的 3-甲基丁基或 4-甲基戊基取代芳烃的分子内 Friedel-Crafts 反应，为构建苯并环提供了一种简便且经济的方法化合物。多种 1,1-二甲基茚满和萘衍生物已由非常简单的原料以高产率和高选择性制备。本策略提供了一个以烷烃为烷基化组分的 Friedel-Crafts 反应的新例子，并构成了选择性 CH 键活化和烷烃衍生物功能化的便捷方法。
• 1,2-Di(lithiomethyl)benzene from phthalan: Sequential introduction of two different electrophiles
  作者：Juan Almena、Francisco Foubelo、Miguel Yus

  DOI：10.1016/0040-4020(95)00064-f

  日期：1995.3

  The reaction of phthalan (1) with an excess of lithium powder and a catalytic amount of DTBB (2.5 mol %) in THF at 20 degrees C followed by treatment with electrophiles (D2O, CO;! and carbonyl compounds) at -78 degrees C leads, after hydrolysis, to the corresponding functionalised benzylic alcohols 3a-g. When the Lithiation reaction is continued, after the reaction with the first electrophile, and a second electrophile (H2O, D2O and carbonyl compounds) is added the corresponding disubstituted compounds 6a-q are prepared. Diols 3c-g and 6h,i,l,n and hydroxyacids 6a,c,f,k are easily dehydrated to the corresponding cyclic ethers (7c-f, 8h,i,l,n) or lactones (9a,c,f,k), respectively. Finally, alcohols 6b,d,e give, after acid treatment, the Friedel-Crafts type benzocyclopentenes 10b,d,e.
• Polyalkyl aromatic hydrocarbons. II. Cyclialkylation of benzenoid hydrocarbons with isoprene
  作者：E. J. Eisenbraun、J. R. Mattox、R. C. Bansal、M. A. Wilhelm、P. W. K. Flanagan、A. B. Carel、R. E. Laramy、M. C. Hamming

  DOI：10.1021/jo01269a065

  日期：1968.5
• Facile Preparation and Molecular Structure of a Novel Metacyclophane
  作者：Jing-Lei Zhang、Qi Shi、Jiang Wu、Yang Wang

  DOI：10.1080/00397910802138645

  日期：2008.6.27

  A novel 1,1,10,10,19,19-hexamethyl-5,14,23-trimethoxy[3.3.3]metacyclophane (2) was prepared in 25% yield by Friedel-Crafts cyclization of 4-(2-methoxyphenyl)-2-methylbutan-2-ol (1) at -78 degrees C using TiCl(4) as Lewis acid catalyst in anhydrous dichloromethane. The structure of cyclophane 2 was determined by single-crystal X-ray diffraction, and the impact of substrate concentration on the yield of macrocycle 2 was also examined. The study on the effect of substituents at the phenyl ring showed that the methoxy group in 1 is crucial for its trimerization to give the hexamethyl[3.3.3]metacyclophane derivative. Demethylation of 2 with BBr(3) gave 1,1,10,10,19,19-hexamethyl-5,14,23-trihydroxy[3.3.3]metacyclophane (4) in 96% yield, and its three hydroxyl groups provide the possible modification sites for further construction of supramolecular assemblies.
• Odeur et constitution XVIII. Sur un dérivé indanique à odeur musquée
  作者：Cl. Ferrero、R. Helg

  DOI：10.1002/hlca.19590420640

  日期：——

  (1) The present paper describes the synthesis of 1,1-dimethyl-4-acetyl-6-t-butyl-indan, and particularly our structure investigation of this very strong musk compound discovered independently by M. G. J. Beets and co-workers and by the authors.

  （1）本文描述了1,1-二甲基-4-乙酰基-6-叔丁基-茚满的合成，特别是我们对这种非常强的麝香化合物的结构研究，该化合物由MGJ甜菜和他的同事以及作者。