(3aS,4R,11S,11aR)-4-methyl-11-((R)-N-methyl-S-phenylsulfonimidoyl)-2,3,3a,4,8,9,10,11-octahydrocyclopenta[d]pyrido[1,2-c][1,3]oxazin-6(1H)-one | 942598-47-2

• 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: (3aS,4R,11S,11aR)-4-methyl-11-((R)-N-methyl-S-phenylsulfonimidoyl)-2,3,3a,4,8,9,10,11-octahydrocyclopenta[d]pyrido[1,2-c][1,3]oxazin-6(1H)-one
• CAS: 942598-47-2
• 化学式: C₁₉H₂₆N₂O₃S
• 分子量: 362.493
• InChiKey: XTUNQEFVHFKPPK-HDQIGCSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  58.97
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3aS,4R,11S,11aR)-4-methyl-11-((R)-N-methyl-S-phenylsulfonimidoyl)-2,3,3a,4,8,9,10,11-octahydrocyclopenta[d]pyrido[1,2-c][1,3]oxazin-6(1H)-one 在 1-氯乙基氯甲酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以74%的产率得到(3aS,4R,11S,11aR)-11-chloro-4-methyl-2,3,3a,4,8,9,10,11-octahydrocyclopenta[d]pyrido[1,2-c][1,3]oxazin-6(1H)-one
  参考文献：
  名称：

  Modular Asymmetric Synthesis of Functionalized Azaspirocycles Based on the Sulfoximine Auxiliary

  摘要：

  A modular asymmetric synthesis of the functionalized azaspirocycles 6 (m = 2, n = 1), 7 (m = 1, n = 2), 8 (m = n = 2), 12, 20, and 24 from the cyclic allylic sulfoximines 1 is described. The synthetic strategy is based on the stereoselective construction of the carbocycle 4 containing the amino-substituted tertiary C atom from 1 followed by the generation of the azaspirocycle. Three different routes have been followed for the synthesis of the heterocyclic ring: N,C-dianion cycloalkylation, ring-closing metathesis, and N-acyl iminium ion formation.

  DOI：

  10.1021/ol0706410
• 作为产物：
  描述：

  (R)-1-((1S,Z)-2-{[(R)-N-methylphenylsulfonimidoyl]methylene}cyclopentyl)ethanol 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 (3aS,4R,11S,11aR)-4-methyl-11-((R)-N-methyl-S-phenylsulfonimidoyl)-2,3,3a,4,8,9,10,11-octahydrocyclopenta[d]pyrido[1,2-c][1,3]oxazin-6(1H)-one
  参考文献：
  名称：

  Modular Asymmetric Synthesis of Functionalized Azaspirocycles Based on the Sulfoximine Auxiliary

  摘要：

  A modular asymmetric synthesis of the functionalized azaspirocycles 6 (m = 2, n = 1), 7 (m = 1, n = 2), 8 (m = n = 2), 12, 20, and 24 from the cyclic allylic sulfoximines 1 is described. The synthetic strategy is based on the stereoselective construction of the carbocycle 4 containing the amino-substituted tertiary C atom from 1 followed by the generation of the azaspirocycle. Three different routes have been followed for the synthesis of the heterocyclic ring: N,C-dianion cycloalkylation, ring-closing metathesis, and N-acyl iminium ion formation.

  DOI：

  10.1021/ol0706410