(2R)-N-nicotinoylbornane-10,2-sultam | 603953-48-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R)-N-nicotinoylbornane-10,2-sultam
• 英文别名: [(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-pyridin-3-ylmethanone；[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-pyridin-3-ylmethanone
• CAS: 603953-48-6
• 化学式: C₁₆H₂₀N₂O₃S
• 分子量: 320.412
• InChiKey: FXMPLKKPXBXUMY-XJKCOSOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-N-nicotinoylbornane-10,2-sultam 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 25.0h， 生成 methyl (1R,11S,12S)-15-benzyl-13-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-9-methyl-9,15-diazatetracyclo[10.3.1.02,10.03,8]hexadeca-2(10),3,5,7,13-pentaene-11-carboxylate
  参考文献：
  名称：

  Asymmetric synthesis of tetracyclic substructures of Strychnos indole alkaloids

  摘要：

  The addition of the enolate of methyl 1-methyl-2-indoleacetate 1 and lithium 2-(lithiomethyl)indole-1-carboxyl ate 5 to pyridines and N-alkylpyridinium salts bearing a chiral auxiliary at the 3-position (tolylsulfinyl, acyl iron complexes, bornane-10,2-sultam), with subsequent acid cyclization of the resulting dihydropyridines, is investigated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00251-9
• 作为产物：
  描述：

  氯化烟碱盐酸盐 、 (2R)-bornane-10,2-sultam 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以92%的产率得到(2R)-N-nicotinoylbornane-10,2-sultam
  参考文献：
  名称：

  Asymmetric synthesis of tetracyclic substructures of Strychnos indole alkaloids

  摘要：

  The addition of the enolate of methyl 1-methyl-2-indoleacetate 1 and lithium 2-(lithiomethyl)indole-1-carboxyl ate 5 to pyridines and N-alkylpyridinium salts bearing a chiral auxiliary at the 3-position (tolylsulfinyl, acyl iron complexes, bornane-10,2-sultam), with subsequent acid cyclization of the resulting dihydropyridines, is investigated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00251-9

文献信息

• Asymmetric synthesis of tetracyclic substructures of Strychnos indole alkaloids
  作者：Mercedes Amat、M.-Dolors Coll、Núria Llor、Carmen Escolano、Elies Molins、Carles Miravitlles、Joan Bosch

  DOI：10.1016/s0957-4166(03)00251-9

  日期：2003.6

  The addition of the enolate of methyl 1-methyl-2-indoleacetate 1 and lithium 2-(lithiomethyl)indole-1-carboxyl ate 5 to pyridines and N-alkylpyridinium salts bearing a chiral auxiliary at the 3-position (tolylsulfinyl, acyl iron complexes, bornane-10,2-sultam), with subsequent acid cyclization of the resulting dihydropyridines, is investigated. (C) 2003 Elsevier Science Ltd. All rights reserved.