3,4-Dibrom-cyclohexancarbonsaeure | 98333-81-4

• 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: 3,4-Dibrom-cyclohexancarbonsaeure
• 英文别名: 3,4-Dibrom-cyclohexan-1-carbonsaeure；3,4-dibromo-cyclohexanecarboxylic acid；3.4-Dibrom-hexahydrobenzoesaeure；3,4-Dibromocyclohexane-1-carboxylic acid
• CAS: 98333-81-4
• 化学式: C₇H₁₀Br₂O₂
• 分子量: 285.963
• InChiKey: LVAHWKWNSWDMDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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

反应信息

• 作为产物：
  描述：

  trans-4-bromo-cyclohexanecarboxylic acid 在 氯仿 、 溴 、 sodium carbonate 作用下， 生成 3,4-Dibrom-cyclohexancarbonsaeure
  参考文献：
  名称：

  Perkin, Journal of the Chemical Society, 1904, vol. 85, p. 422

  摘要：

  DOI：

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 COMPANY, LIMITED

  公开号：US20150239909A1

  公开（公告）日：2015-08-27

  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 (1) which is a key intermediate in the synthesis of edoxaban, a compound that exhibits on 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 dicholoromethane, toluene, tetrahydrofuran, ethyl acetate, hexanes, cyclopentyl methyl ether (CPME) or a misture thereof to get (1S, 4S 5S)-4-bromo-6-oxabicyclo[3.2.1]octan-y-one of formula (1)

  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-酮的方法，该化合物被表示为以下式子(1)，是合成依度沙班的关键中间体，依度沙班是一种对活化血凝因子X（也称为活化因子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。该方法包括将式子(II)的(1S)-环己-3-烯-1-羧酸与一种溴化剂反应，所述溴化剂选自N-溴代琥珀酰亚胺或1,3-二溴-5,5-二甲基异噻唑酮，以及在以下溶剂中的一种或混合物中，在选择的碱金属氧化物或羟化物中，反应得到式子(1)的(1S,4S,5S)-4-溴-6-氧代双环[3.2.1]辛-7-酮。所述溶剂包括二氯甲烷、甲苯、四氢呋喃、乙酸乙酯、己烷、环戊基甲醚（CPME）或其混合物。
• Perkin; Tattersall, Journal of the Chemical Society, 1907, vol. 91, p. 495
  作者：Perkin、Tattersall

  DOI：——

  日期：——
• γ-lactones and γ-thiolactones—I
  作者：B. Bochwic、A. Frankowski

  DOI：10.1016/s0040-4020(01)96839-5

  日期：1968.1
• [EN] FLAME RETARDED STYRENIC POLYMER FOAMS AND FOAM PRECURSORS<br/>[FR] MOUSSES POLYMÈRES STYRÉNIQUES IGNIFUGÉEET PRÉCURSEURS DES MOUSSES
  申请人：ALBEMARLE CORP

  公开号：WO2008106334A2

  公开（公告）日：2008-09-04

  [EN] This invention provides styrenic polymer foams, especially expanded and/or extruded styrenic polymer foams, which are flame retarded by use of one or more flame retardants. These flame retardants are (i) at least one compound having the formula: where R is hydrogen, a methyl group, a linear or branched substituted or unsubstituted aliphatic group having from two to about six carbon atoms, or a halogenated linear or branched substituted or unsubstituted aliphatic group having from two to about six carbon atoms, (ii) a compound having the formula: or (iii) a combination of (i) and (ii).
  [FR] L'invention concerne des mousses polymères styréniques, en particulier des mousses polymères styréniques expansées et/ou extrudées, qui sont ignifugées à l'aide d'un ou de plusieurs additifs d'ignifugation. Ces additifs sont: i) au moins un composé de la formule, dans laquelle R représente hydrogène, un groupe méthyle, un groupe aliphatique substitué ou non substitué, linéaire ou ramifié ayant de deux à environ six atomes de carbone, ou un groupe aliphatique substitué ou non substitué, linéaire ou ramifié, halogéné ayant de deux à environ six atomes de carbone, (ii) un composé de la formule, ou (iii) une combinaison de (i) et (ii).