(+)-N-(hexahydro-2,5β-methano-1H-3aS,3aα,6aα-cyclopenta[c]pyrrol-4α-yl)-4-methylbenzenesulfonamide | 175670-09-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-N-(hexahydro-2,5β-methano-1H-3aS,3aα,6aα-cyclopenta[c]pyrrol-4α-yl)-4-methylbenzenesulfonamide
• 英文别名: N-[(3S,4R,5R,7R)-1-Azatricyclo[3.3.1.03,7]nonan-4-yl]-4-methylbenzenesulfonamide
• CAS: 175670-09-4
• 化学式: C₁₅H₂₀N₂O₂S
• 分子量: 292.402
• InChiKey: KKYAUEJSZYYAQK-CTHBEMJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-N-(hexahydro-2,5β-methano-1H-3aS,3aα,6aα-cyclopenta[c]pyrrol-4α-yl)-4-methylbenzenesulfonamide 在 calcium 作用下， 以 四氢呋喃 、 氨 为溶剂， 反应 0.5h， 以100%的产率得到hexahydro-2,5β-methano-1H-3aS,3aα,6aα-cyclopenta[c]pyrrol-4α-amine
  参考文献：
  名称：

  Enantioselective synthesis of dual serotonergic azanoradamantane SC-52491

  摘要：

  A racemic synthesis of azanoradamantane (+/-)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00680-8
• 作为产物：
  描述：

  (-)-3R-[[(4-methylphenyl)sulfonyl]amino]bicyclo[2.2.1]hept-5-ene-2αR carboxylic acid 在 硼烷 、 氨 、 臭氧 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 乙酸乙酯 、 丙酮 、 乙腈 为溶剂， -78.0~60.0 ℃ 、344.74 kPa 条件下， 反应 269.25h， 生成 (+)-N-(hexahydro-2,5β-methano-1H-3aS,3aα,6aα-cyclopenta[c]pyrrol-4α-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Enantioselective synthesis of dual serotonergic azanoradamantane SC-52491

  摘要：

  A racemic synthesis of azanoradamantane (+/-)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00680-8

文献信息

• Use of atom-transfer radical cyclizations as an efficient entry into a new “serotonergic” azanoradamantane
  作者：Daniel L. Flynn、Daniel P. Becker、Roger Nosal、Daniel L. Zabrowski

  DOI：10.1016/s0040-4039(00)60166-1

  日期：1992.11

  route to azanoradamantanes is described which makes use of an atom-transfer radical cyclization to afford 3-azabicyclo[3.3.0]octanes and . Subsequent elaboration of exo-allylamine functionality, followed by cyclization of the endo-hydroxymethyl intermediate , affords the new azanoradamantanes and . This new azatricyclic system is useful for producing serotonin 5-HT3 antagonists and 5-HT4 agonists.

  描述了一种通往金刚烷金刚烷的途径，该途径利用原子转移自由基环化来提供3-氮杂双环[3.3.0]辛烷和。随后的exo-alalamine功能的详细说明，然后环化内羟甲基中间体，得到了新的金刚烷金刚烷和。这种新的氮三环系统可用于生产5-羟色胺5-HT3拮抗剂和5-HT4激动剂。
• Enantioselective synthesis of dual serotonergic azanoradamantane SC-52491
  作者：Daniel P. Becker、Robert K. Husa、Alan E. Moormann、Clara I. Villamil、Daniel L. Flynn

  DOI：10.1016/s0040-4020(99)00680-8

  日期：1999.10

  A racemic synthesis of azanoradamantane (+/-)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e. (C) 1999 Elsevier Science Ltd. All rights reserved.