{4,5-dimethoxy-2-[1-(2-methyl-[1,3]dioxolan-2-yl)propyl]phenyl}(3,4-dimethoxyphenyl)methanone

• 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: {4,5-dimethoxy-2-[1-(2-methyl-[1,3]dioxolan-2-yl)propyl]phenyl}(3,4-dimethoxyphenyl)methanone
• 英文别名: 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-phenyl]-pentan-2-one-ethylene ketal；[4,5-Dimethoxy-2-[1-(2-methyl-1,3-dioxolan-2-yl)propyl]phenyl]-(3,4-dimethoxyphenyl)methanone
• 化学式: C₂₄H₃₀O₇
• 分子量: 430.498
• InChiKey: GWMGOGYAVCWCMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  {4,5-dimethoxy-2-[1-(2-methyl-[1,3]dioxolan-2-yl)propyl]phenyl}(3,4-dimethoxyphenyl)methanone 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以32%的产率得到3-[2-(3,4-二甲氧基苯甲酰基)-4,5-二甲氧基苯基]戊-2-酮
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF 3-[2-(3,4-DIMETHOXY-BENZOYL)-4,5-DIMETHOXY-PHENYL]-PENTAN-2-ONE
  [FR] PROCEDE DE PREPARATION DE 3-[2-(3,4-DIMETHOXY-BENZOYL)-4,5-DIMETHOXY-PHENYL]-PENTAN-2-ONE

  摘要：

  该发明涉及一种从一般式（II）化合物（其中R1和R2分别代表C1-4-烷基或一起形成C2-6-烷基）出发制备式（I）的3-[2-(3,4-二甲氧基苯甲酰基)-4,5-二甲氧基苯基]-戊-2-酮的过程。

  公开号：

  WO2004054951A1
• 作为产物：
  描述：

  3-(2-bromo-4,5-dimethoxyphenyl)pentan-2-one 在 正己基锂 、 对甲苯磺酸 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 26.0h， 生成 {4,5-dimethoxy-2-[1-(2-methyl-[1,3]dioxolan-2-yl)propyl]phenyl}(3,4-dimethoxyphenyl)methanone
  参考文献：
  名称：

  New, Lithiation-Based Synthesis of Tofisopam, a 2,3-Benzodiazepine Type Anxiolytic Drug

  摘要：

  The classical, widely-used synthesis of the anxiolytic drug tofisopam applies chromium(VI) oxide reagent for the synthesis of the diketone key intermediate. The chromium salts formed in the course of the reaction are strongly toxic compounds. In order to reduce the reagents contributing to the pollution of the environment, an alternative manufacturing process has been elaborated at our laboratory. Starting compound (3,4-dimethoxyphenyl)acetone was transformed to the ethylene ketal of (2-bromo-4,5-dimethoxyphenyl)acetone. Bromine-lithium exchange and introduction of a 3,4-dimethoxybenzoyl moiety resulted in the new key intermediate. Removal of the ketal protecting group and ring closure with hydrazine was carried out in one pot affording drug substance tofisopam.

  DOI：

  10.3987/com-13-s(s)15

文献信息

• New, Lithiation-Based Synthesis of Tofisopam, a 2,3-Benzodiazepine Type Anxiolytic Drug
  作者：Erika Molnárné Samu、Balázs Volk、Gyula Lukács、Gyula Simig

  DOI：10.3987/com-13-s(s)15

  日期：——

  The classical, widely-used synthesis of the anxiolytic drug tofisopam applies chromium(VI) oxide reagent for the synthesis of the diketone key intermediate. The chromium salts formed in the course of the reaction are strongly toxic compounds. In order to reduce the reagents contributing to the pollution of the environment, an alternative manufacturing process has been elaborated at our laboratory. Starting compound (3,4-dimethoxyphenyl)acetone was transformed to the ethylene ketal of (2-bromo-4,5-dimethoxyphenyl)acetone. Bromine-lithium exchange and introduction of a 3,4-dimethoxybenzoyl moiety resulted in the new key intermediate. Removal of the ketal protecting group and ring closure with hydrazine was carried out in one pot affording drug substance tofisopam.
• [EN] PROCESS FOR THE PREPARATION OF 3-[2-(3,4-DIMETHOXY-BENZOYL)-4,5-DIMETHOXY-PHENYL]-PENTAN-2-ONE<br/>[FR] PROCEDE DE PREPARATION DE 3-[2-(3,4-DIMETHOXY-BENZOYL)-4,5-DIMETHOXY-PHENYL]-PENTAN-2-ONE
  申请人：EGYT GYOGYSZERVEGYESZETI GYAR

  公开号：WO2004054951A1

  公开（公告）日：2004-07-01

  The invention relates to a process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-phenyl]-pentan-2-one of the Formula (I) starting from a compound of the general Formula (II) (wherein R1 and R2 each stands for C1-4-alkyl or together form C2-6-alkylene).

  该发明涉及一种从一般式（II）化合物（其中R1和R2分别代表C1-4-烷基或一起形成C2-6-烷基）出发制备式（I）的3-[2-(3,4-二甲氧基苯甲酰基)-4,5-二甲氧基苯基]-戊-2-酮的过程。