methyl 1-chloro-N-(methoxymethyl)pyrido[3,4-b]indole-3-carboxylate | 1040742-81-1

• 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: methyl 1-chloro-N-(methoxymethyl)pyrido[3,4-b]indole-3-carboxylate
• 英文别名: Methyl 1-chloro-9-(methoxymethyl)pyrido[3,4-b]indole-3-carboxylate
• CAS: 1040742-81-1
• 化学式: C₁₅H₁₃ClN₂O₃
• 分子量: 304.733
• InChiKey: RJMMNEKHVBEMOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-chloro-N-(methoxymethyl)pyrido[3,4-b]indole-3-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 三氟甲磺酸 、 四乙基氯化铵 、 原甲酸三甲酯 作用下， 以 甲醇 、 硝基甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 methyl 1-acetyl-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  First Total Syntheses of 1,3-Disubstituted β-Carboline Alkaloids, Dichotomide I and Marinacarbolines A-D

  摘要：

  The first total syntheses of dichotomide I (1), and marinacarbolines A-D (3-6) were achieved in four steps from methyl 1-chloro-beta-carboline-3-carboxlyate (9), which was previously used as a synthetic intermediate of dichotomine C. The required compound 9 was prepared in a six-step sequence including a microwave-assisted thermal electrocyclic reaction of a 1-azahexatriene system.

  DOI：

  10.3987/com-12-12630
• 作为产物：
  描述：

  3-iodo-1-(methoxymethyl)indole-2-carboxaldehyde 在 草酰氯 、 盐酸羟胺 、 sodium acetate 、 palladium diacetate 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 11.5h， 生成 methyl 1-chloro-N-(methoxymethyl)pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  First Total Syntheses of 1,3-Disubstituted β-Carboline Alkaloids, Dichotomide I and Marinacarbolines A-D

  摘要：

  The first total syntheses of dichotomide I (1), and marinacarbolines A-D (3-6) were achieved in four steps from methyl 1-chloro-beta-carboline-3-carboxlyate (9), which was previously used as a synthetic intermediate of dichotomine C. The required compound 9 was prepared in a six-step sequence including a microwave-assisted thermal electrocyclic reaction of a 1-azahexatriene system.

  DOI：

  10.3987/com-12-12630

文献信息

• The Enantioselective Total Synthesis of a .BETA.-Carboline Alkaloid, (S)-(-)-Dichotomine C
  作者：Kana Omura、Tominari Choshi、Shiroh Watanabe、Yuhsuke Satoh、Junko Nobuhiro、Satoshi Hibino

  DOI：10.1248/cpb.56.237

  日期：——

  The first enantioselective synthesis of a β-carboline alkaloid, dichotomine C, possessing antiallergic effects, was achieved by constructing a β-carboline framework based on the microwave-assisted thermal electrocyclic reaction of a 1-azahexatriene system, followed by the Sharpless asymmetric dihydroxylation.

  通过构建基于 1-azahexatriene 体系微波辅助热电环反应的 β-咔啉框架，然后进行 Sharpless 不对称二羟基化反应，首次对映选择性合成了具有抗过敏作用的 β-咔啉生物碱--二氢托明 C。
• First Total Syntheses of 1,3-Disubstituted β-Carboline Alkaloids, Dichotomide I and Marinacarbolines A-D
  作者：Satoshi Hibino、Tominari Choshi、Shinji Tagawa、Asuka Okamoto、Takashi Nishiyama、Shiroh Watanabe、Noriyuki Hatae

  DOI：10.3987/com-12-12630

  日期：——

  The first total syntheses of dichotomide I (1), and marinacarbolines A-D (3-6) were achieved in four steps from methyl 1-chloro-beta-carboline-3-carboxlyate (9), which was previously used as a synthetic intermediate of dichotomine C. The required compound 9 was prepared in a six-step sequence including a microwave-assisted thermal electrocyclic reaction of a 1-azahexatriene system.