(4-bromo-3,5-dimethylphenyl)methylene diacetate | 74973-54-9

• 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: (4-bromo-3,5-dimethylphenyl)methylene diacetate
• 英文别名: 4-bromo-3,5-dimethylbenzylidene diacetate；[Acetyloxy-(4-bromo-3,5-dimethylphenyl)methyl] acetate；[acetyloxy-(4-bromo-3,5-dimethylphenyl)methyl] acetate
• CAS: 74973-54-9
• 化学式: C₁₃H₁₅BrO₄
• 分子量: 315.164
• InChiKey: WOCDQDMIETTXDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-bromo-3,5-dimethylphenyl)methylene diacetate 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 生成 2-bromo-5-(methoxymethyl)-1,3-dimethylbenzene
  参考文献：
  名称：

  The synthesis of trisnorcybrodolide, A metabolite of brodie.

  摘要：

  DOI：

  10.1016/s0040-4039(00)93644-x
• 作为产物：
  描述：

  2-溴-1,3,5-三甲基苯 、 乙酸酐 在 chromium(VI) oxide 、 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 以41%的产率得到(4-bromo-3,5-dimethylphenyl)methylene diacetate
  参考文献：
  名称：

  The total synthesis of the cybrodins

  摘要：

  本文描述了从2-溴二甲苯（6）出发，合成环孢多醇（1）、异环孢多醇（2）、环孢醇（3）、环孢酸（4）和三降环孢内酯（5）的总过程。该路线涉及通过铬酰醋酸氧化6的5-甲基团，通过芳基锂化和与环氧乙烷反应添加β-羟乙基链，并通过芳基锂化和用氯甲酸乙酯处理添加第五个碳取代基，得到关键中间体，即甲基3-(2-羟乙基)-6-甲氧甲基-2,4-二甲基苯甲酸酯（18d）。后者被转化为三降环孢内酯（5），并通过相应的醛21进一步细化成剩余的环孢素。

  DOI：

  10.1139/v81-311

文献信息

• The total synthesis of the cybrodins
  作者：William A. Ayer、Robert H. McCaskill

  DOI：10.1139/v81-311

  日期：1981.7.15

  The total syntheses of cybrodol (1), isocybrodol (2), cybrodal (3), cybrodic acid (4), and trisnorcybrodolide (5), starting from 2-bromomesitylene (6) are described. The route involves oxidation of the 5-methyl group of 6 by means of chromyl acetate, addition of the β-hydroxyethyl chain by aryllithiation and reaction with ethylene oxide, and addition of the fifth carbon substituent by aryllithiation and treatment with ethyl chloroformate to give the key intermediate, methyl 3-(2-hydroxyethyl)-6-methoxymethyl-2,4-dimethylbenzoate (18d). The latter was transformed into trisnorcybrodolide (5), and further elaborated via the corresponding aldehyde 21 into the remaining cybrodins.

  本文描述了从2-溴二甲苯（6）出发，合成环孢多醇（1）、异环孢多醇（2）、环孢醇（3）、环孢酸（4）和三降环孢内酯（5）的总过程。该路线涉及通过铬酰醋酸氧化6的5-甲基团，通过芳基锂化和与环氧乙烷反应添加β-羟乙基链，并通过芳基锂化和用氯甲酸乙酯处理添加第五个碳取代基，得到关键中间体，即甲基3-(2-羟乙基)-6-甲氧甲基-2,4-二甲基苯甲酸酯（18d）。后者被转化为三降环孢内酯（5），并通过相应的醛21进一步细化成剩余的环孢素。
• Synthesis and structure–activity relationships of phenyl-substituted coumarins with anti-tubercular activity that target FadD32
  作者：Tomohiko Kawate、Noriaki Iwase、Motohisa Shimizu、Sarah A. Stanley、Samantha Wellington、Edward Kazyanskaya、Deborah T. Hung

  DOI：10.1016/j.bmcl.2013.09.035

  日期：2013.11

  In an effort to develop new and potent agents for therapy against tuberculosis, a high-throughput screen was performed against Mycobacterium tuberculosis strain H37Rv. Two 6-aryl-5,7-dimethyl-4-phenylcoumarin compounds 1a and 1b were found with modest activity. A series of coumarin derivatives were synthesized to improve potency and to investigate the structure-activity relationship of the series. Among them, compounds 1o and 2d showed improved activity with IC90 of 2 mu M and 0.5 mu M, respectively. Further optimization provided compound 3b with better physiochemical properties with IC90 0.4 mu M which had activity in a mouse model of infection. The role of the conformation of the 4- and 6-aryl substituents is also described. (c) 2013 Elsevier Ltd. All rights reserved.
• The synthesis of trisnorcybrodolide, A metabolite of brodie.
  作者：William A. Ayer、Robert H. McCaskill

  DOI：10.1016/s0040-4039(00)93644-x

  日期：1980.1