Dibromocyclohexanoic acid

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: Dibromocyclohexanoic acid
• 英文别名: 4,4-dibromocyclohexane-1-carboxylic acid
• 化学式: C₇H₁₀Br₂O₂
• 分子量: 285.96
• InChiKey: DMRHPBQXNQHKNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

文献信息

• [EN] PROCESS FOR THE PREPARATION OF (1S,4S,5S)-4-BROMO-6-OXABICYCLO[3.2.1] OCTAN-7-ONE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE (1S,4S,5S)-4-BROMO-6-OXABICYCLO[3.2.1]OCTAN-7-ONE
  申请人：DAIICHI SANKYO CO LTD

  公开号：WO2014081047A1

  公开（公告）日：2014-05-30

  The present invention relates to an improved and industrially advantageous process for the preparation of (1S, 4S, 5S) -4-bromo-6-oxabicyclo [3.2.1] octan-7-one represented by the following formula (I) which is a key intermediate in the synthesis of edoxaban, a compound that exhibits an inhibitory effect on activated blood coagulation factor X (also referred to as activated factor X or FXa), and is useful as a preventive and/or therapeutic drug for thrombotic diseases. The process includes reacting (1S) -cyclohex-3-ene-1-carboxylic acid of formula (II) with a brominating agent selected from the group consisting of N-bromosuccinimide or 1, 3-dibromo-5, 5-dimethylhydantoin in the presence of a base selected from calcium oxide or calcium hydroxide in a solvent selected from the group comprising of dichloromethane, toluene, tetrahydrofuran, ethy1 acetate, hexanes, cyclopentyl methyl ether (CPME) or a mixture thereof to get ( 1S, 4S, 5S) -4-bromo-6-oxabicyclo [3.2.1] octan-7-one of formula (I).

  本发明涉及一种改良的、具有工业优势的制备(1S, 4S, 5S)-4-溴-6-氧代双环[3.2.1]辛-7-酮（化学式（I））的方法，该化合物是合成依度沙班的关键中间体，依度沙班是一种对激活的血液凝血因子X（也称为激活因子X或FXa）具有抑制作用的化合物，可用作预防和/或治疗血栓性疾病的药物。该方法包括将化学式（II）的(1S)-环己-3-烯-1-羧酸与从N-溴代琥珀酰亚胺或1,3-二溴-5,5-二甲基海因酰脲中选择的溴化试剂，在选择自氧化钙或氢氧化钙中的一种碱和二氯甲烷、甲苯、四氢呋喃、乙酸乙酯、己烷、环戊基甲醚（CPME）或其混合物为溶剂的条件下反应，得到化学式（I）的(1S, 4S, 5S)-4-溴-6-氧代双环[3.2.1]辛-7-酮。
• PROCESS FOR THE PREPARATION OF (1S,4S,5S)-4-BROMO-6-OXABICYCLO[3.2.1]OCTAN-7-ONE
  申请人：Daiichi Sankyo Co., Ltd.

  公开号：EP2922833A1

  公开（公告）日：2015-09-30