rac-5,6-dihydro-6-methyl-7,7-dioxothieno[2,3-b]thiopyran-4-one | 894793-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-5,6-dihydro-6-methyl-7,7-dioxothieno[2,3-b]thiopyran-4-one
• 英文别名: 5,6-dihydro-4-oxo-(S)-6-methyl-thieno[2,3-b]thiopyran-7,7-dioxide；5,6-dihydro-4H-6-methylthieno[2,3-b]thiopyran-4-one-7,7-dioxide；(S)-5,6-Dihydro-6-methylthieno[2,3-b]thiopyran-4-one 7,7-dioxide；6-methyl-7,7-dioxo-5,6-dihydrothieno[2,3-b]thiopyran-4-one
• CAS: 894793-33-0
• 化学式: C₈H₈O₃S₂
• 分子量: 216.282
• InChiKey: LQUUXMUPBQBKHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  87.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rac-5,6-dihydro-6-methyl-7,7-dioxothieno[2,3-b]thiopyran-4-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以95.2%的产率得到5,6-dihydro-4-hydroxy-(S)-6-methyl-thieno[2,3-b]thiopyran-7,7-dioxide
  参考文献：
  名称：

  [EN] PROCESS FOR PREPARING DORZOLAMIDE HYDROCHLORIDE AND ITS INTERMEDIATE
  [FR] PROCÉDÉ POUR LA PRÉPARATION DE CHLORHYDRATE DE DORZOLAMIDE ET SES INTERMÉDIAIRES

  摘要：

  本发明涉及一种改进的制备过程，用于制备(4S,6S)-4-(乙基氨基)-5,6-二氢-6-甲基-4H-噻吩[2,3-b]噻吩基喹噁啉-2-磺酰胺-7,7-二氧化氢盐酸盐（“多索胺盐酸盐”），其化学和对映体纯度高。本发明还涉及公式20的新型中间体及其制备过程。多索胺盐酸盐通过本发明的方法制备，可用于治疗青光眼，通过抑制碳酸酐酶酶起作用。

  公开号：

  WO2010061398A1
• 作为产物：
  描述：

  在 lithium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以272.5 mg的产率得到rac-5,6-dihydro-6-methyl-7,7-dioxothieno[2,3-b]thiopyran-4-one
  参考文献：
  名称：

  膦催化CS3的[3 + 2]环化/迈克尔酸加成反应，形成2-硫代乙烯基乙烯基硫化物

  摘要：

  我们已经开发了DPPE催化的γ-取代的脲基甲酸酯和CS 2的三分子两组分串联反应，通过膦催化的[3 + 2]环化反应和随后的Michael加成反应来构建2-硫代乙烯基乙硫醚。通过精确合成抗青光眼剂证明了2-亚硫基乙烯基硫的合成值。

  DOI：

  10.1039/d0cc05070a

文献信息

• Process for obtaining 4-hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-7,7-dioxide and its enantiomers, and applications thereof
  申请人：Ragactives, S.L.

  公开号：EP2128161A1

  公开（公告）日：2009-12-02

  The invention relates to a process for obtaining cis-4-hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-7,7-dioxide, its enantiomers or mixtures thereof, by reduction of 5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-4-one-7,7-dioxide with a reducing agent which generates hydride ions. The obtained compounds are useful as intermediates in the synthesis of chiral active ingredients.

  该发明涉及一种通过用产生氢化物离子的还原剂还原5,6-二氢-6-甲基-4H-噻吩[2,3-b]噻吩吡喃-4-酮-7,7-二氧化物，从而获得顺式-4-羟基-6-甲基-5,6-二氢-4H-噻吩[2,3-b]噻吩吡喃-7,7-二氧化物，其对映体或其混合物的过程。所得化合物在手性活性成分合成中作为中间体有用。
• METHOD FOR SEPARATING OF OPTICALLY PURE THIOPHENE COMPOUNDS USING SIMULATED MOVING BED CHROMATOGRAPHY
  申请人：Koh Jae Suk

  公开号：US20090234140A1

  公开（公告）日：2009-09-17

  Disclosed herein is a method of producing an optically active thiophene-based compound using a simulated moving bed adsorption separation process, and more specifically, a method of continuously separating a racemic thiophene-based compound into its optically active thiophene-based compounds having high purity, through optical resolution using the simulated moving bed process. According to the method of the current invention, a racemic mixture of a thiophene-based compound can be continuously separated into its optically active thiophene-based compounds having high purity, which is an intermediate of optically active dorzolamide acting as a topical therapeutic agent for glaucoma, using a simulated moving bed adsorption separation technique, thereby increasing industrial usability.

  本发明公开了一种使用模拟移动床吸附分离工艺生产光学活性噻吩基化合物的方法，更具体地说，本发明公开了一种通过模拟移动床工艺进行光学分辨，将混合的噻吩基化合物连续分离成高纯度的光学活性噻吩基化合物的方法。根据本发明的方法，可以使用模拟移动床吸附分离技术将噻吩基化合物的混合物连续分离成高纯度的光学活性噻吩基化合物，该化合物是治疗青光眼的局部治疗剂光学活性多索胺的中间体，从而提高了其工业可用性。
• [EN] PROCESS FOR OBTAINING 4-HYDROXY-6-METHYL-5, 6-DIHYDRO-4H-THIENO [2,3-b] THIOPYRAN-7, 7-DIOXIDE AND ITS ENANTIOMERS, AND APPLICATIONS THEREOF<br/>[FR] PROCÉDÉ D'OBTENTION DE 4-HYDROXY-6-MÉTHYL-5,6-DIHYDRO-4H-THIÉNO [2,3-B] THIOPYRAN-7,7-DIOXYDE ET SES ÉNANTIOMÈRES, ET SES APPLICATIONS
  申请人：RAGACTIVES S L U

  公开号：WO2009144263A2

  公开（公告）日：2009-12-03

  The invention relates to a process for obtaining cis-4- hydroxy-6-methyl-5, 6-dihydro-4H-thieno [2, 3-b] thiopyran-7, 7- dioxide, its enantiomers or mixtures thereof, by reduction of 5, 6-dihydro-6-methyl-4H-thieno [2, 3-b] thiopyran-4-one-7, 7 -dioxide with a reducing agent which generates hydride ions. The obtained compounds are useful as intermediates in the synthesis of chiral active ingredients.
• Phosphine catalyzed [3+2] cyclization/Michael addition of allenoate with CS₂ to form 2-thineyl vinyl sulfide
  作者：Weihong Fei、Ping Xu、Jie Hou、Weijun Yao

  DOI：10.1039/d0cc05070a

  日期：——

  have developed a DPPE-catalyzed three molecular two component tandem reaction of γ-substituted allenoate and CS2 to construct 2-thineyl vinyl sulfide through phosphine catalyzed [3+2] cyclization followed by Michael addition. The synthetic value of the 2-thineyl vinyl sulfide was demonstrated by a concise synthesis of an anti-glaucoma agent.

  我们已经开发了DPPE催化的γ-取代的脲基甲酸酯和CS 2的三分子两组分串联反应，通过膦催化的[3 + 2]环化反应和随后的Michael加成反应来构建2-硫代乙烯基乙硫醚。通过精确合成抗青光眼剂证明了2-亚硫基乙烯基硫的合成值。
• [EN] PROCESS FOR PREPARING DORZOLAMIDE HYDROCHLORIDE AND ITS INTERMEDIATE<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE CHLORHYDRATE DE DORZOLAMIDE ET SES INTERMÉDIAIRES
  申请人：SUVEN LIFE SCIENCES LTD

  公开号：WO2010061398A1

  公开（公告）日：2010-06-03

  The present invention relates to an improved process for the preparation of (4S,6S)-4- (ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide hydrochloride ("Dorzolamide hydrochloride") having formula 1. Dorzolamide hydrochloride is prepared by the process of the present invention with high chemical and diastereomeric purity. The present invention also relates to novel intermediate of the formula 20 and a process for its preparation. Dorzolamide hydrochloride is useful in the treatment of ocular hypertension by inhibiting carbonic anhydrase enzyme.

  本发明涉及一种改进的制备过程，用于制备(4S,6S)-4-(乙基氨基)-5,6-二氢-6-甲基-4H-噻吩[2,3-b]噻吩基喹噁啉-2-磺酰胺-7,7-二氧化氢盐酸盐（“多索胺盐酸盐”），其化学和对映体纯度高。本发明还涉及公式20的新型中间体及其制备过程。多索胺盐酸盐通过本发明的方法制备，可用于治疗青光眼，通过抑制碳酸酐酶酶起作用。