1-methyl-2-(2',2',5',5'-tetramethyl-tetrahydro-1',3',4',6',8'-pentaxocyclopenta[a]indene-8'a-carbonyl)-1,2,3,4-tetrahydro-9-methyl-pyrido[3,4]indole | 393781-06-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-methyl-2-(2',2',5',5'-tetramethyl-tetrahydro-1',3',4',6',8'-pentaxocyclopenta[a]indene-8'a-carbonyl)-1,2,3,4-tetrahydro-9-methyl-pyrido[3,4]indole
• 英文别名: [(1R)-1,9-dimethyl-3,4-dihydro-1H-pyrido[3,4-b]indol-2-yl]-[(1R,2S,6R,8S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecan-6-yl]methanone
• CAS: 393781-06-1
• 化学式: C₂₅H₃₂N₂O₆
• 分子量: 456.539
• InChiKey: NVQLGXCJRBMXKX-NTFFJPLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-methyl-2-(2',2',5',5'-tetramethyl-tetrahydro-1',3',4',6',8'-pentaxocyclopenta[a]indene-8'a-carbonyl)-1,2,3,4-tetrahydro-9-methyl-pyrido[3,4]indole 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以70%的产率得到1-methyl-1,2,3,4-tetrahydro-9-methyl-pyrido[3,4-b]indole
  参考文献：
  名称：

  Diastereoselective Alkylation of 2,3,4,6-Di-O-isopropylidene-2-keto-l-gulonic Amides. Application to the Asymmetric Synthesis of 1-Substituted-1,2,3,4-tetrahydroisoquinolines and 1-Substituted-1,2,3,4,-tetrahydro-β-carbolines

  摘要：

  The diastereoselective alkylation of amides 3a,b and 7a,b derived from gulonic acid is described. Substituted compounds are obtained in good yield and high diastereoselectivity. A mechanistic investigation establishes that the diastereoselectivity did not arise from an initial asymmetric deprotonation. The stereochemistry is then determined during the alkylation step.

  DOI：

  10.1021/jo0155658
• 作为产物：
  描述：

  1,2,3,4-四氢-9H-吡啶[3,4-B]并吲哚 在 N-甲基吗啉 、 四甲基乙二胺 、 叔丁基锂 、 potassium hydride 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.25h， 生成 1-methyl-2-(2',2',5',5'-tetramethyl-tetrahydro-1',3',4',6',8'-pentaxocyclopenta[a]indene-8'a-carbonyl)-1,2,3,4-tetrahydro-9-methyl-pyrido[3,4]indole
  参考文献：
  名称：

  Diastereoselective Alkylation of 2,3,4,6-Di-O-isopropylidene-2-keto-l-gulonic Amides. Application to the Asymmetric Synthesis of 1-Substituted-1,2,3,4-tetrahydroisoquinolines and 1-Substituted-1,2,3,4,-tetrahydro-β-carbolines

  摘要：

  The diastereoselective alkylation of amides 3a,b and 7a,b derived from gulonic acid is described. Substituted compounds are obtained in good yield and high diastereoselectivity. A mechanistic investigation establishes that the diastereoselectivity did not arise from an initial asymmetric deprotonation. The stereochemistry is then determined during the alkylation step.

  DOI：

  10.1021/jo0155658