2-[4-(4-chlorophenyl)cyclohexyl]-2,3-dichloro-2,3-dihydro-1,4-naphthoquinone | 1100053-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[4-(4-chlorophenyl)cyclohexyl]-2,3-dichloro-2,3-dihydro-1,4-naphthoquinone
• CAS: 1100053-59-5
• 化学式: C₂₂H₁₉Cl₃O₂
• 分子量: 421.751
• InChiKey: NPCSIBJFNDUTDZ-PAXUEANESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-[4-(4-chlorophenyl)cyclohexyl]-2,3-dichloro-2,3-dihydro-1,4-naphthoquinone 在 sodium acetate 作用下， 反应 1.0h， 以3.66 kg的产率得到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：

  1,4-萘醌 在 ammonium peroxydisulfate 、 氯 、 silver nitrate 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 生成 2-[4-(4-chlorophenyl)cyclohexyl]-2,3-dichloro-2,3-dihydro-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