trans-2-[4-(4-cyclohexyl)chlorophenyl]-1,4-naphthoquinone | 1100053-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: trans-2-[4-(4-cyclohexyl)chlorophenyl]-1,4-naphthoquinone
• CAS: 1100053-58-4
• 化学式: C₂₂H₁₉ClO₂
• 分子量: 350.845
• InChiKey: CHXRCCJFHHYDBA-KOMQPUFPSA-N

物化性质

• 沸点：
  508.9±50.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trans-2-[4-(4-cyclohexyl)chlorophenyl]-1,4-naphthoquinone 在 sodium acetate 、 氯 、 溶剂黄146 作用下， 反应 1.0h， 生成 2-[4-(4-chlorophenyl)cyclohexyl]-3-chloro-1,4-naphthoquinone
  参考文献：
  名称：

  A Single-Pot Synthesis of Atovaquone: An Antiparasitic Drug of Choice

  摘要：

  The present article relates to a practical, economically viable, and validated at industrial scale, single-pot synthetic route for preparation of atovaquone, one of the most versatile antiparasitic drugs of choice used for the prophylaxis and treatment of diseases such as pneumocystis, toxoplasmosis, babesiosis, coccidiosis, and malaria. However, owing to the extremely poor yields of synthesis and very high doses of treatment (due to poor bioavailability) the cost of treatment with this drug is not affordable by the patients in need, particularly in the third world countries where these diseases are most prevalent. Unlike most of the reported processes which use 2-chloronaphthoquinone and pure trans-4-chlorophenyl cyclohexane carboxylic acid, our process is based on the decarboxylative alkylation of isomeric mixture of 4-chlorophenyl cyclohexane carboxylic acid with 1,4-naphthoquinone to give 42% overall yield of atovaquone, 10 times higher than from the reported process (4%) from the innovators of this drug.

  DOI：

  10.1021/op500032w
• 作为产物：
  描述：

  4-(4-Chlorophenyl)Cyclohexanecarboxylic Acid 、 1,4-萘醌 在 ammonium peroxydisulfate 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 以20.8%的产率得到trans-2-[4-(4-cyclohexyl)chlorophenyl]-1,4-naphthoquinone
  参考文献：
  名称：

  A Single-Pot Synthesis of Atovaquone: An Antiparasitic Drug of Choice

  摘要：

  The present article relates to a practical, economically viable, and validated at industrial scale, single-pot synthetic route for preparation of atovaquone, one of the most versatile antiparasitic drugs of choice used for the prophylaxis and treatment of diseases such as pneumocystis, toxoplasmosis, babesiosis, coccidiosis, and malaria. However, owing to the extremely poor yields of synthesis and very high doses of treatment (due to poor bioavailability) the cost of treatment with this drug is not affordable by the patients in need, particularly in the third world countries where these diseases are most prevalent. Unlike most of the reported processes which use 2-chloronaphthoquinone and pure trans-4-chlorophenyl cyclohexane carboxylic acid, our process is based on the decarboxylative alkylation of isomeric mixture of 4-chlorophenyl cyclohexane carboxylic acid with 1,4-naphthoquinone to give 42% overall yield of atovaquone, 10 times higher than from the reported process (4%) from the innovators of this drug.

  DOI：

  10.1021/op500032w

文献信息

• NEW PROCESS FOR PREPARATION OF ATOVAQUONE AND NOVEL INTERMEDIATES THEREOF
  申请人：Kumar Ashok

  公开号：US20100081847A1

  公开（公告）日：2010-04-01

  Disclosed herein is a novel process for preparation of atovaquone. The process includes reacting 1,4-naphthoquinone with trans-4-(4-chlorophenyl) cyclohexane carboxylic acid followed by halogenation to obtain a dihalo-compound. Further, dehydrohalogenation of the dihalo-compound produces a monohalogeno-compound which under goes hydrolysis to produce atovaquone. The invention also discloses atovaquone in a substantially pure and well defined polymorphic form designated as “Form IPCA-ATO,” and the preparation thereof.

  本文披露了一种用于制备阿托伐醌的新型工艺。该工艺包括将1,4-萘醌与反式-4-(4-氯苯基)环己烷羧酸反应，然后进行卤化以获得二卤化合物。此外，二卤化合物的脱卤化产生单卤化合物，经水解生成阿托伐醌。该发明还披露了一种名为“Form IPCA-ATO”的高度纯净和明确定义的多晶形态的阿托伐醌，以及其制备方法。
• Process for preparation of atovaquone and novel intermediates thereof
  申请人：IPCA Laboratories Limited

  公开号：US07847127B2

  公开（公告）日：2010-12-07

  Disclosed herein is a novel process for preparation of atovaquone. The process includes reacting 1,4-naphthoquinone with trans-4-(4-chlorophenyl) cyclohexane carboxylic acid followed by halogenation to obtain a dihalo-compound. Further, dehydrohalogenation of the dihalo-compound produces a monohalogeno-compound which under goes hydrolysis to produce atovaquone. The invention also discloses atovaquone in a substantially pure and well defined polymorphic form designated as “Form IPCA-ATO,” and the preparation thereof.

  本文披露了一种制备阿托伐醌的新工艺。该工艺包括将1,4-萘醌与反-4-(4-氯苯基)环己烷羧酸反应，然后进行卤代反应以获得二卤化合物。进一步，对二卤化合物进行脱卤反应产生单卤代化合物，该化合物经水解反应生成阿托伐醌。本发明还披露了一种被称为“Form IPCA-ATO”的高度纯净和定义明确的多晶形态的阿托伐醌及其制备方法。
• US7847127B2
  申请人：——

  公开号：US7847127B2

  公开（公告）日：2010-12-07
• [EN] ALKENE QUINONE COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS D'ALCÈNE QUINONE ET PROCÉDÉS D'UTILISATION
  申请人：[en]UNIVERSITY OF PITTSBURGH - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION

  公开号：WO2022204381A1

  公开（公告）日：2022-09-29

  Disclosed herein are new pharmacological therapies that increase CYB5R3 activity, improve vascular function and limit inflammation by restoring the redox balance in CVD. In one embodiment, disclosed herein are compounds that include an alkyl chain containing a nitroalkene group conjugated to a quinone-containing moiety.