(3R,4S)-ethyl 9-acetyl-3-benzyl-6-methyl-2-oxo-2,3,4,9-tetrahydropyrano[2,3-b]indole-4-carboxylate | 1377322-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3R,4S)-ethyl 9-acetyl-3-benzyl-6-methyl-2-oxo-2,3,4,9-tetrahydropyrano[2,3-b]indole-4-carboxylate
• 英文别名: ethyl (3R,4S)-9-acetyl-3-benzyl-6-methyl-2-oxo-3,4-dihydropyrano[2,3-b]indole-4-carboxylate
• CAS: 1377322-10-5
• 化学式: C₂₄H₂₃NO₅
• 分子量: 405.45
• InChiKey: TZYSUSMIMPBKHB-NQIIRXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-chloro-3-phenyl-propionaldehyde 、 ethyl 2-(1-acetyl-5-methyl-2-oxoindolin-3-ylidene)acetate 在 (-)-(5aS,10bR)-5a,10b-二氢-2-(2,4,6-三甲基苯基)-4H,6H-茚并[2,1-b][1,2,4]三唑[4,3-d][1,4]氯化恶唑鎓一水合物 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.6h， 以82%的产率得到(3R,4S)-ethyl 9-acetyl-3-benzyl-6-methyl-2-oxo-2,3,4,9-tetrahydropyrano[2,3-b]indole-4-carboxylate
  参考文献：
  名称：

  N-Heterocyclic Carbene (NHC)-Catalyzed Highly Diastereo- and Enantioselective Oxo-Diels–Alder Reactions for Synthesis of Fused Pyrano[2,3-b]indoles

  摘要：

  A chiral N-heterocyclic carbene (NHC)-catalyzed Diels-Alder reaction of 2-oxoindolin-3-ylidenes and alpha-chloroaldehydes was developed for the synthesis of fused pyrano[2,3-b]indoles in good to excellent yields (up to 99%) with high cis-diastereoselectivities (>99:1 dr) and enantioselectivities (up to >99% ee).

  DOI：

  10.1021/ol301175z

文献信息

• <i>N</i>-Heterocyclic Carbene (NHC)-Catalyzed Highly Diastereo- and Enantioselective Oxo-Diels–Alder Reactions for Synthesis of Fused Pyrano[2,3-<i>b</i>]indoles
  作者：Limin Yang、Fei Wang、Pei Juan Chua、Yunbo Lv、Liang-Jun Zhong、Guofu Zhong

  DOI：10.1021/ol301175z

  日期：2012.6.1

  A chiral N-heterocyclic carbene (NHC)-catalyzed Diels-Alder reaction of 2-oxoindolin-3-ylidenes and alpha-chloroaldehydes was developed for the synthesis of fused pyrano[2,3-b]indoles in good to excellent yields (up to 99%) with high cis-diastereoselectivities (>99:1 dr) and enantioselectivities (up to >99% ee).