(R)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine-5,5-dioxide | 175340-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: (R)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine-5,5-dioxide
• 英文别名: (S)-2,3-dihydro-[3,4]cyclopentano-1,2,4-benzothiadiazine-1,1-dioxide；S18986；1H-Pyrrolo[2,1-c][1,2,4]benzothiadiazine, 2,3,3a,4-tetrahydro-, 5,5-dioxide, (3aR)-；(3aR)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide
• CAS: 175340-21-3
• 化学式: C₁₀H₁₂N₂O₂S
• 分子量: 224.283
• InChiKey: MNTIJYGEITVWHU-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-Dihydro-1H-pyrrolo<2,1-c><1,2,4>benzothiadiazin-5,5-dioxid 在 lithium aluminium tetrahydride 、 (+)-(2S,4R)-4-dimethylamino-3-methyl-1,2-diphenyl-2-butanol 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 (R)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine-5,5-dioxide 、 (3aS)-2,3,3a，4-四氢-1H-吡咯并[2,1-c][1,2,4]苯并噻二嗪-5,5-二氧化物
  参考文献：
  名称：

  Enantioselective synthesis of a pyrrolo-benzothiadiazine derivative S 18986, a new AMPA receptor positive modulator

  摘要：

  Enantioselective reduction of pyrrolo-benzothiadiazine 6 using various chiral reducing agents has been studied and led to efficient synthesis of 8 (S 18986) which was established to be of (S) configuration by single crystal X-ray diffraction analysis. S 18986 is a potent and selective AMPA positive modulator which displays total stereoselectivity, the (R) enantiomer being completely inactive. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00547-1

文献信息

• Enantioselective synthesis of a pyrrolo-benzothiadiazine derivative S 18986, a new AMPA receptor positive modulator
  作者：P. Desos、B. Serkiz、P. Morain、J. Lepagnol、A. Cordi

  DOI：10.1016/s0960-894x(96)00547-1

  日期：1996.12

  Enantioselective reduction of pyrrolo-benzothiadiazine 6 using various chiral reducing agents has been studied and led to efficient synthesis of 8 (S 18986) which was established to be of (S) configuration by single crystal X-ray diffraction analysis. S 18986 is a potent and selective AMPA positive modulator which displays total stereoselectivity, the (R) enantiomer being completely inactive. Copyright (C) 1996 Elsevier Science Ltd
• The synthesis of S 18986, a chiral AMPA receptor modulator, via catalytic asymmetric hydrogenation
  作者：Christopher J. Cobley、Elsa Foucher、Jean-Pierre Lecouve、Ian C. Lennon、James A. Ramsden、Gilles Thominot

  DOI：10.1016/s0957-4166(03)00547-0

  日期：2003.11

  The asymmetric hydrogenation of a dihydropyrrolo-benzothiadiazine dioxide 1 with a diphosphine ruthenium diamine catalyst has been used to synthesize the AMPA receptor positive modulator tetrahydropyrrolo-benzothiadiazine dioxide 2 (S 18986) in high enantiomeric excess. The use of factorial experimental design led to significant improvements in the process parameters and improved enantioselectivity. (C) 2003 Elsevier Ltd. All rights reserved.