1-acetoxymethyl-2,3,4,5,6-pentamethylbenzene | 19936-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-acetoxymethyl-2,3,4,5,6-pentamethylbenzene
• 英文别名: pentamethylbenzyl acetate；2,3,4,5,6-Pentamethylbenzyl acetate；(2,3,4,5,6-pentamethylphenyl)methyl acetate
• CAS: 19936-85-7
• 化学式: C₁₄H₂₀O₂
• mdl: MFCD00119123
• 分子量: 220.312
• InChiKey: HNYCNHWRRXKSTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-acetoxymethyl-2,3,4,5,6-pentamethylbenzene 在 potassium carbonate 作用下， 生成 2,3,4,5,6-五甲基苯甲醇
  参考文献：
  名称：

  Jacobsen, Chemische Berichte, 1889, vol. 22, p. 1217

  摘要：

  DOI：
• 作为产物：
  描述：

  五甲基苯 在 氢溴酸 、 溶剂黄146 作用下， 反应 21.5h， 生成 1-acetoxymethyl-2,3,4,5,6-pentamethylbenzene
  参考文献：
  名称：

  Negative-Working Photosensitive Poly(phenylene ether) Based on Poly(2,6-dimethyl-1,4-phenylene ether), a Cross-Linker, and a Photoacid Generator

  摘要：

  A novel benzyl cation type cross-linker, hex-1,6-ylenebis[oxy(2,4,6-tris(acetyloxymethyl)-3,5-dimethylbenzene)] (ROAD), that suppresses acid-catalyzed self-polycondensation has been developed. Furthermore, a negative-working, photosensitive poly(phenylene ether) (PSPPE) based on poly(2,6-dimethyl-1,4-phenylene ether) (PPE), HOAD, and diphenylidonium 9,10-dimethoxyanthracene-2-sulfonate (DIAS) as a photoacid generator (PAG) has been developed. This resist system does not contain a high thermal curing process. The resist consisting of PPE (83 wt %), HOAD (10 wt %), and DIAS (7 wt %) showed excellent sensitivity (D-0.5) of 43 mJ/cm(2) and high contrast (gamma(0.5)) of 11 when it was exposed to 365 nm wavelength UV light (i-line), postexposure baked (PEB) at 190 degrees C for 5 min, and developed by dipping in toluene at 25 degrees C. A fine negative-type pattern having 6 mu m resolution oil 2.4 mu m thick film on a silicon wafer was obtained by exposure to 300 mJ/cm(2) of the i-line by using a contact-printed mode. The resulting PSPPE film, cured at 220 degrees C for 111 under nitrogen, had a low dielectric constant (epsilon: 2.61), good thermal stability, and low water absorption.

  DOI：

  10.1021/ma902526r

文献信息

• The Liquid-phase Oxidation of Methylbenzenes by the Cobalt-Copper-Bromide System
  作者：Toshihiko Okada、Yoshio Kamiya

  DOI：10.1246/bcsj.54.2724

  日期：1981.9

  The liquid-phase oxidation of methylbenzenes catalyzed by a catalyst system composed of cobalt(II) and copper(II) acetates and sodium bromide was carried out in acetic acid at 150 °C. The corresponding benzyl acetates and benzaldehydes were obtained in high selectivities in most cases. A nuclear-brominated product, i.e., 3-bromo-4-methoxytoluene was also obtained in the oxidation of p-methoxytoluene

  由乙酸钴（II）和乙酸铜（II）和溴化钠组成的催化剂体系催化甲基苯的液相氧化，在乙酸中于 150 °C 下进行。在大多数情况下，以高选择性获得相应的乙酸苄酯和苯甲醛。在对甲氧基甲苯的氧化中也得到核溴化产物，即3-溴-4-甲氧基甲苯，其具有两个不同的反应位点，即供电子甲氧基取代基的邻位和苄基位。然而，在催化剂体系中溴离子取代乙酸根离子对侧链氧化产物具有令人满意的选择性。在对二甲苯氧化中，还得到了α,α'-二乙酰氧基-对二甲苯和对（乙酰氧基甲基）苯甲酸，以及对甲基乙酸苄酯，虽然他们的金额很小。还进行了多甲基苯的氧化。
• The amidoalkylation of aromatic hydrocarbons
  作者：John E. Barry、Edward A. Mayeda、Sidney D. Ross

  DOI：10.1016/0040-4020(77)80088-4

  日期：1977.1

  The Nyberg procedure (the use of trifluoroacetic acid in chloroform) for the efficient amidoalkylation of aromatic hydrocarbons is limited to substrates more nucleophilic than benzene. The reaction involves protonation of the electrophile, cleavage to a carbonium ion and alkylation of the nucleophile by the carbonium ion. Either the cleavage step or the alkylation step may be rate-determining. The

  Nyberg程序（在氯仿中使用三氟乙酸）进行芳烃的有效酰胺烷基化仅限于比苯更具亲核性的底物。该反应包括亲电体的质子化，裂解成碳酸根离子和通过碳酸根离子使亲核体烷基化。裂解步骤或烷基化步骤可以是速率确定的。本工作确定了某些形成碳离子但不能使亲核试剂烷基化的情况（以苯和硝基取代苯作为亲核试剂），以及其他反应条件不足以允许质子化的亲电试剂裂解的情况。N-邻苯二甲酰亚胺甲基酰胺）。
• Effective and Versatile Functionalisation of Hexamethylbenzene Using N-F Reagents
  作者：Stojan Stavber、Petra Kralj、Marko Zupan

  DOI：10.1055/s-2001-15150

  日期：——

  Effective direct introduction of alkoxy, amido, azido or halogeno functional groups on the benzylic position in hexamethylbenzene was mediated by the N-F reagents F-TEDA-BF4, NFTh, NFSi or FP-B800 in the presence of alcohols, carboxylic acids, cyanides or trimethylsilyl derivatives as sources of an external nucleophile.

  通过使用N-F试剂F-TEDA-BF4、NFTh、NFSi或FP-B800，在醇类、羧酸、氰化物或三甲基硅烷衍生物作为外源亲核试剂的存在下，实现了在六甲基苯的苄位上有效引入烷氧基、酰氨基、叠氮基或卤素官能团。
• SUBSTITUTED IMIDAZOLES
  申请人：CHUBB NATHAN ANTHONY LOGAN

  公开号：US20070167506A1

  公开（公告）日：2007-07-19

  This invention relates to a range of alpha substituted 2-benzyl substituted imidazole compounds and pharmaceutically acceptable salts and solvates thereof, to compositions comprising such compounds, processes for their synthesis and their use as parasiticides.

  本发明涉及一系列α取代的2-苄基取代咪唑化合物及其药用可接受盐和溶剂化合物，包括这些化合物的组合物、合成过程以及它们作为驱虫剂的用途。
• Remarkable Effect of Water on Functionalization of the Phenyl Ring in Methyl-Substituted Benzene Derivatives with F-TEDA-BF₄
  作者：Petra Kralj、Marko Zupan、Stojan Stavber

  DOI：10.1021/jo060213s

  日期：2006.5.1

  reagents reacted with hexamethylbenzene (1) forming side chain substituted alkoxides or esters in protic solvents, Ritter type side chain functionalization was observed in acetonitrile in the presence of trifluoroacetic acid, while in aqueous acetonitrile solution phenyl ring transformation took place, starting with ipso attack of water and further rearrangement of the methyl group as the main process. Rearranged

  各种NF试剂与六甲基苯（1）在质子溶剂中反应形成侧链取代的醇盐或酯，在三氟乙酸存在下在乙腈中观察到Ritter型侧链官能化，而在乙腈水溶液中发生苯环转化，开始以ipso攻击水和进一步重新排列甲基为主要过程。重排的2,3,4,5,6,6-六甲基环己-2,4-二烯酮（7）被转化为5-氟-2,3,5,6,6-五甲基-4-亚甲基环己基-2-en- 1-酮（8）或5-羟基-2,3,5,6,6-五甲基-4-亚甲基环己基-2-烯-1-酮（9）。1,2,3,4,5,6-六甲基双环[2.2.0] hexa-2,5-二烯与F-TEDA-BF 4反应在水的存在下，以高收率形成7。Durene（12）对水的ipso攻击行为与1类似，但另一方面1,2,3,4-四甲基苯具有不同的区域选择性，并形成2,3,4,5-四甲基苯酚，进一步转化为4-氟- 2,3,4,5-四甲基环己-2,5-二烯酮。遵守二阶速率方程v = d [NF]

表征谱图