8-acetamido-1,4-benzodioxane-5-carboxylic acid | 66411-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 8-acetamido-1,4-benzodioxane-5-carboxylic acid
• 英文别名: 8-(acetylamino)-2,3-dihydro-1,4-benzodioxin-5-carboxylic acid；8-acetamino-1,4-benzodioxane-5-carboxylic acid；8-Acetamido-1,4-benzodioxan-5-carboxylic acid；5-acetamido-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid
• CAS: 66411-27-6
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: LYCFLVALOZTFDX-UHFFFAOYSA-N

物化性质

• 沸点：
  476.2±45.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-acetamido-1,4-benzodioxane-5-carboxylic acid 在 N-氯代丁二酰亚胺 、 溶剂黄146 作用下， 反应 8.0h， 以67.7%的产率得到8-amino-7-chloro-2,3-dihydro-benzo[1,4]dioxine-5-carboxylic acid
  参考文献：
  名称：

  Pilot Scale Process Development of SL65.0102-10, an N-Diazabicyclo[2.2.2]-octylmethyl Benzamide

  摘要：

  The process development and improvements for route selection, adapted to large scale for the pilot-scale preparation of SL65.0102-10, an N-diazabicyclo[2.2.2]-octylmethyl benzamide, a 5-HT3 and 5-HT4 receptor active ligand for the treatment of neurological disorders such as cognition impairment, are described in this article. Notable steps and enhancements are compared to the original route, including the improvement of a chiral epoxide synthesis by shortening the number of chemical steps, the deprotection of a quaternary ammonium salt, and the redesign of the final amidification coupling to avoid chromatography.

  DOI：

  10.1021/acs.oprd.6b00262
• 作为产物：
  描述：

  8-氨基-2,3-二氢-苯并[1,4]二噁英-5-羧酸 在 乙酸酐 、 溶剂黄146 作用下， 以84%的产率得到8-acetamido-1,4-benzodioxane-5-carboxylic acid
  参考文献：
  名称：

  Substituted 2,3-alkylene bis (oxy) benzamides and derivatives and method

  摘要：

  揭示了新型取代的2,3-烷基双(氧基)苯甲酰胺及其衍生物。还公开了一种生产该类化合物的方法。这些化合物具有抗焦虑、精神刺激、解禁和抗抑郁特性，在心理功能领域中具有治疗作用，特别是在胃肠病学、心脏病学、泌尿学、风湿病学和妇科学中。

  公开号：

  US04186135A1

文献信息

• Substituted 2,3-alkylene bis (oxy) benzamides and derivatives
  申请人：Siociete d'Etudes Scientifiques et Industrielles de L'ile-de-France

  公开号：US04255580A1

  公开（公告）日：1981-03-10

  Novel substituted 2,3-alkylene bis (oxy) benzamides and derivatives thereof are disclosed. Also disclosed is a method for producing said compounds. The compounds have anxiolytic, psychostimulant, disinhibiting and thymoanaleptic properties useful therapeutically in the psychofunctional field, particularly in gastro-enterology, cardiology, urology, rheumatology and gynaecology.

  本发明揭示了新型的2,3-烷基双（氧）苯甲酰胺及其衍生物。同时，还揭示了一种制备该化合物的方法。这些化合物具有抗焦虑、精神兴奋、解抑制和情绪提升的特性，在心理功能领域中有治疗作用，特别是在胃肠病学、心脏病学、泌尿学、风湿病学和妇科学中有用。
• Substituted 2,3-alkylene bis(oxy) benzamides and derivatives to treat
  申请人：Societe d'Etudes Scientifiques et Industrielles de l'Ile-de-France

  公开号：US04248885A1

  公开（公告）日：1981-02-03

  Novel substituted 2,3-alkylene bis (oxy) benzamides and derivatives thereof are disclosed. Also disclosed is a method for producing said compounds. The compounds have anxiolytic, psychostimulant, disinhibiting and thymoanaleptic properties useful therapeutically in the psychofunctional field, particularly in gastro-enterology, cardiology, urology, rheumatology and gynaecology.

  本发明揭示了替代了2,3-烷基双（氧）苯甲酰胺及其衍生物。同时还揭示了制备该化合物的方法。该化合物具有抗焦虑、兴奋剂、抑制剂和抗抑郁剂等特性，在心理功能领域中具有治疗作用，特别是在胃肠病学、心脏病学、泌尿科学、风湿病学和妇科学等方面有用。
• Substituted 2,3-alkylene di (oxy) benzamides and derivatives
  申请人：Societe d'Etudes Scientifiques et Industrielles de L'ile-de-France

  公开号：US04323503A1

  公开（公告）日：1982-04-06

  Novel substituted 2,3-alkylene bis (oxy) benzamides and derivatives thereof are disclosed. Also disclosed is a method for producing said compounds. The compounds have anxiolytic, psychostimulant, disinhibiting and thymoanaleptic properties useful therapeutically in the psychofunctional field, particularly in gastro-enterology, cardiology, urology, rheumatology and gynaecology.

  本发明披露了替代2,3-烷基双（氧）苯甲酰胺及其衍生物的新型化合物。同时还披露了一种制备这些化合物的方法。这些化合物具有抗焦虑、精神兴奋、解抑制和情绪调节等特性，在心理功能领域中具有治疗作用，特别是在胃肠病学、心脏病学、泌尿学、风湿病学和妇科学等方面。
• Substituted 2,3-alkylene bis (oxy)-4,5 (or 5,6) azimido benzamides and
  申请人：Societe d'Etudes Scientifiques et Industrielles de l'Ile

  公开号：US04306072A1

  公开（公告）日：1981-12-15

  Novel substituted 2,3-alkylene bis (oxy) benzamide azimido compounds and derivatives thereof are disclosed as for example N-(1-allyl-2-pyrrolidylmethyl)-7,8-azimido-1,4-benzodioxane-5-carboxamide and N-(1-allyl-2-pyrrolidylmethyl)-6,7-azimido-1,4-benzodioxane-5-carboxamide. The compounds have anxiolytic, psychostimulant, disinhibiting and thymoanaleptic properties useful therapeutically in the psychofunctional field, particularly in gastro-enterology, cardiology, urology, rheumatology and gynaecology.

  本发明涉及替代2,3-烷基双(氧)苯甲酰胺偶氮化合物及其衍生物，例如N-(1-烯丙基-2-吡咯烷甲基)-7,8-偶氮基-1,4-苯并二氧杂环戊烷-5-羧酰胺和N-(1-烯丙基-2-吡咯烷甲基)-6,7-偶氮基-1,4-苯并二氧杂环戊烷-5-羧酰胺。这些化合物具有抗焦虑、兴奋剂、解禁和抗抑郁性质，在心理功能领域中具有治疗作用，特别是在胃肠病学、心脏病学、泌尿学、风湿病学和妇科学中。
• Tricyclic heterocyclic compounds as 5-HT.sub.4 receptor antagonists
  申请人：SmithKline Beecham plc

  公开号：US05705509A1

  公开（公告）日：1998-01-06

  Compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein X.sub.1 --(CH.sub.2).sub.x --X.sub.2 and the aromatic carbon atoms to which they are attached form 5-7 membered ring wherein X.sub.1 is O or S; X.sub.2 is O, S, NR.sub.5 or NR.sub.6 CO wherein R.sub.5 is hydrogen or C.sub.1-6 alkyl; or one of X.sub.1 and X.sub.2 is O, S or CH.sub.2 and the other is CH.sub.2 ; x is 1, 2 or 3; R.sub.1 and R.sub.2 together are Q--CH.sub.2 --CH.sub.2, Q--CH.dbd.CH, or Q--CH.dbd.N where Q is linked either to the R.sub.1 or the R.sub.2 substitution position and Q is O, S or NR.sub.t wherein R.sub.t is hydrogen or C.sub.1-6 alkyl; R.sub.3 is hydrogen halo, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or amino; R.sub.4.sup.1 and R.sub.4.sup.2 are independently hydrogen or C.sub.1-6 alkyl; Y is O or NH; Z is of sub-formula (a), (b) or (c) and their use as pharmaceuticals in the treatment of gastrointestinal disorders, cardiovascular disorders and CNS disorders. ##STR1##

  化合物的式子（I）或其药学上可接受的盐，其中X.sub.1--(CH.sub.2).sub.x--X.sub.2和它们所连接的芳香碳原子形成5-7元环，其中X.sub.1是O或S；X.sub.2是O，S，NR.sub.5或NR.sub.6 CO，其中R.sub.5是氢或C.sub.1-6烷基；或者X.sub.1和X.sub.2中的一个是O，S或CH.sub.2，另一个是CH.sub.2；x为1、2或3；R.sub.1和R.sub.2在一起是Q--CH.sub.2--CH.sub.2，Q--CH.dbd.CH或Q--CH.dbd.N，其中Q链接到R.sub.1或R.sub.2取代位置之一，Q为O，S或NR.sub.t，其中R.sub.t为氢或C.sub.1-6烷基；R.sub.3为氢卤素，C.sub.1-6烷基，C.sub.1-6烷氧基或氨基；R.sub.4.sup.1和R.sub.4.sup.2分别为氢或C.sub.1-6烷基；Y为O或NH；Z为亚式（a）、（b）或（c）的亚基，并用作治疗胃肠道疾病、心血管疾病和中枢神经系统疾病的药物。