(S)-(-)-5,6-Dihydro-N-(2-methylpropyl)-4H-thieno<2,3-b>thiopyran-4-amine 7,7-Dioxide | 131352-45-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-(-)-5,6-Dihydro-N-(2-methylpropyl)-4H-thieno<2,3-b>thiopyran-4-amine 7,7-Dioxide
• 英文别名: (4S)-N-(2-methylpropyl)-7,7-dioxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-amine
• CAS: 131352-45-9
• 化学式: C₁₁H₁₇NO₂S₂
• 分子量: 259.393
• InChiKey: QNRAZCVKFAQJMT-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(-)-5,6-Dihydro-N-(2-methylpropyl)-4H-thieno<2,3-b>thiopyran-4-amine 7,7-Dioxide 生成 1,6,7,7a-Tetrahydro-1-(2-methylpropyl)-2,4,5-trithia-1-azacyclopentindene 2,2,5,5-tetraoxide 、 (+)-(S)-4-(2-甲基丙基氨基)-5,6-二氢-4H-噻吩并[2,3-b]噻喃-2-磺酰胺7,7-二氧化盐酸
  参考文献：
  名称：

  An asymmetric synthesis of MK-0417. Observations on oxazaborolidine-catalyzed reductions

  摘要：

  Enantiomerically pure MK-0417 has been prepared in nine steps from thiophene. The key reactions in the sequence were an oxazaborolidine-catalyzed borane reduction followed by a tosylation/amine displacement. The borane reduction was studied in detail, and observations regarding substituents on the oxazaborolidine catalyst and the intricacies of the reaction are reported, as well as a mild method for recovering the enantiomerically pure amino alcohol derived from the catalyst.

  DOI：

  10.1021/jo00002a050
• 作为产物：
  描述：

  (R)-(+)-5,6-Dihydro-4H-thieno<2,3-b>thiopyran-4-ol 7,7-Dioxide 在 sodium acetylide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (S)-(-)-5,6-Dihydro-N-(2-methylpropyl)-4H-thieno<2,3-b>thiopyran-4-amine 7,7-Dioxide
  参考文献：
  名称：

  An asymmetric synthesis of MK-0417. Observations on oxazaborolidine-catalyzed reductions

  摘要：

  Enantiomerically pure MK-0417 has been prepared in nine steps from thiophene. The key reactions in the sequence were an oxazaborolidine-catalyzed borane reduction followed by a tosylation/amine displacement. The borane reduction was studied in detail, and observations regarding substituents on the oxazaborolidine catalyst and the intricacies of the reaction are reported, as well as a mild method for recovering the enantiomerically pure amino alcohol derived from the catalyst.

  DOI：

  10.1021/jo00002a050

文献信息

• Process for obtaining 4-(N-alkylamino)-5,6-dihydro-4H-thien-(2,3-b)-thiopyran-2-sulfonamide-7,7-dioxides and intermediates
  申请人：RAGACTIVES, S.L.

  公开号：US20030220509A1

  公开（公告）日：2003-11-27

  The process for obtaining 4-(N-alkylamino)-5,6-dihydro-4H-thien-(2,3-b)-thiopyran-2-sulfonamide-7,7-dioxides (I) wherein R 1 is H or C 1-5 alkyl, and R 2 is C 1-5 alkyl, starts from the corresponding 4-(N-alkylamino)-5,6-dihydro-4H-thien-(2,3-b)-thiopyran-7,7-dioxides, and comprises protecting the alkylamine group, introducing a sulfonamide group and eliminating protecting group. Some compounds of formula (I) are inhibitors of the carbonic anhydrase and can be used in the treatment of elevated intraocular pressure. 1

  获得4-（N-烷基氨基）-5,6-二氢-4H-噻-（2,3-b）噻吩-2-磺酰胺-7,7-二氧化物（I）的过程，其中R1为H或C1-5烷基，R2为C1-5烷基，始于相应的4-（N-烷基氨基）-5,6-二氢-4H-噻-（2,3-b）噻吩-7,7-二氧化物，并包括保护烷基胺基，引入磺酰胺基团和消除保护基。公式（I）的一些化合物是碳酸酐酶的抑制剂，可用于治疗眼内压升高。
• Chiral catalysts for reduction of ketones and process for their preparation
  申请人：MERCK & CO. INC.

  公开号：EP0453298A2

  公开（公告）日：1991-10-23

  The chiral catalyst of general structure 1, or its enantiomer is prepared by treating the corresponding N-carboxy anhydride of structure 2 with an aryl metal, especially a phenyl metal such as an aryl magnesium halide, aryl lithium, aryl zinc or aryl cesium, to form a 1,1-diaryl- methanol of structure 3 followed by treatment with a compound of structure, 4 The catalyst, wherein R is aromatic, is novel and in some cases superior to the catalyst wherein R is alkyl or aralkyl in directing the chirality of borane-dimethyl sulfide reductions of ketones to secondary alcohols.

  一般结构 1 的手性催化剂或其对映体 或其对映体是通过处理结构 2 中相应的 N-羧基酸酐制备的 用芳基金属，特别是苯基金属，如芳基卤化镁、芳基锂、芳基锌或芳基铯，生成结构 3 的 1,1-二芳基甲醇 然后用结构 4 的化合物处理 该催化剂（其中 R 为芳香族）是一种新型催化剂，在某些情况下优于 R 为烷基或芳烷基的催化剂，可引导硼烷-二甲基硫醚将酮还原成仲醇的手性。
• Enantiospecific synthesis of S(+)-5,6-dihydro-4-(R-amino)-4H thieno (2,3-B)thiopyran-2-sulfonamide-7,7-dioxide
  申请人：MERCK & CO. INC.

  公开号：EP0453288A1

  公开（公告）日：1991-10-23

  5,6-Dihydro-4-(R-amino)-4H-thieno[2,3-b]-thiopyran-2-sulfonamide-7,7-dioxide is a potent carbonic anhydrase inhibitor useful in the treatment of ocular hypertension and glaucoma. The S-(+)-enantiomer of that compound, the more active enantiomer, is prepared by a process involving an intermediate step of an enantioselective reduction of a carbonyl group employing an oxazaborolidine chiral catalyst.

  5,6-二氢-4-(R-氨基)-4H-噻吩并[2,3-b]-噻喃-2-磺酰胺-7,7-二氧化物是一种有效的碳酸酐酶抑制剂，可用于治疗眼压过高和青光眼。该化合物的 S-(+)-对映体是活性较高的对映体，其制备过程包括利用噁唑硼烷手性催化剂对羰基进行对映选择性还原的中间步骤。
• METHOD FOR OBTAINING 4-(N-ALKYLAMINE)-5, 6-DIHYDRO-4H-THIENO-(2,3-B)-THIOPYRAN-2-SULFAMIDE-7, 7-DIOXIDES AND INTERMEDIATE PRODUCTS
  申请人：Ragactives, S.L.

  公开号：EP1329453A1

  公开（公告）日：2003-07-23

  The process for obtaining 4-(N-alkylamino)-5,6-dihydro-4H-thien-(2,3-b)-thiopyran-2-sulfonamide-7,7-dioxides (I) wherein R1 is H or C1-5 alkyl, and R2 is C1-5 alkyl, starts from the corresponding 4-(N-alkylamino)-5,6-dihydro-4H-thien-(2,3-b)-thiopyran-7,7-dioxides, and comprises protecting the alkylamine group, introducing a sulfonamide group and eliminating protecting group. Some compounds of formula (I) are inhibitors of the carbonic anhydrase and can be used in the treatment of elevated intraocular pressure.

  获得 4-(N-烷基氨基)-5,6-二氢-4H-噻吩-(2,3-b)-噻喃-2-磺酰胺-7,7-二氧 化物(I)的工艺，其中 R1 是 H 或 C1-5 烷基，R2 是 C1-5 烷基、从相应的 4-(N-烷基氨基)-5,6-二氢-4H-噻吩-(2,3-b)-噻喃-7,7-二氧 化物开始，包括保护烷基胺基团、引入磺酰胺基团和消除保护基团。一些式（I）化合物是碳酸酐酶的抑制剂，可用于治疗眼压升高。
• Asymmetric Transfer Hydrogenation of Imines
  作者：Nobuyuki Uematsu、Akio Fujii、Shohei Hashiguchi、Takao Ikariya、Ryoji Noyori

  DOI：10.1021/ja960364k

  日期：1996.1.1