(3E)-3-[4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)butylidene]piperidine-2,6-dione | 1027201-99-5

• 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: (3E)-3-[4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)butylidene]piperidine-2,6-dione
• CAS: 1027201-99-5
• 化学式: C₂₀H₂₃N₃O₂
• 分子量: 337.422
• InChiKey: XPXRTAHEIXMAAD-WLRTZDKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3E)-3-[4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)butylidene]piperidine-2,6-dione 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 Hg(OAc)2*EDTA 、 三氟乙酸吡啶 、 二异丁基氢化铝 、 sodium cyanoborohydride 、 sodium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 54.92h， 生成
  参考文献：
  名称：

  Stereoselective Synthesis of the Indole Alkaloids Nitrarine, Nitramidine, and Isomers. A Biomimetic Approach

  摘要：

  Starting from tryptamine and dimeric piperidine derivative 8, the synthesis of 4, an immediate precursor in the biosynthesis of the Nitraria alkaloids, was accomplished. Cyclization of this achiral intermediate in aqueous solution produced a mixture of natural nitramidine 17 and one of its stereoisomers. Stereoselective reductions of these iminium salts with several reductors produced nitrarine (1), isonitrarine (2), and two new isomeric Nitraria indole alkaloids.

  DOI：

  10.1021/jo00103a048
• 作为产物：
  描述：

  (5E)-5-(2,6-dioxopiperidin-3-ylidene)pentanal 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (3E)-3-[4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)butylidene]piperidine-2,6-dione
  参考文献：
  名称：

  Stereoselective Synthesis of the Indole Alkaloids Nitrarine, Nitramidine, and Isomers. A Biomimetic Approach

  摘要：

  Starting from tryptamine and dimeric piperidine derivative 8, the synthesis of 4, an immediate precursor in the biosynthesis of the Nitraria alkaloids, was accomplished. Cyclization of this achiral intermediate in aqueous solution produced a mixture of natural nitramidine 17 and one of its stereoisomers. Stereoselective reductions of these iminium salts with several reductors produced nitrarine (1), isonitrarine (2), and two new isomeric Nitraria indole alkaloids.

  DOI：

  10.1021/jo00103a048

文献信息

• Stereoselective Synthesis of the Indole Alkaloids Nitrarine, Nitramidine, and Isomers. A Biomimetic Approach
  作者：Martin J. Wanner、Gerrit-Jan Koomen

  DOI：10.1021/jo00103a048

  日期：1994.12

  Starting from tryptamine and dimeric piperidine derivative 8, the synthesis of 4, an immediate precursor in the biosynthesis of the Nitraria alkaloids, was accomplished. Cyclization of this achiral intermediate in aqueous solution produced a mixture of natural nitramidine 17 and one of its stereoisomers. Stereoselective reductions of these iminium salts with several reductors produced nitrarine (1), isonitrarine (2), and two new isomeric Nitraria indole alkaloids.