methyl 1-benzyl-5-ethyl-2-(1H-indol-3-yl)piperidine-4-carboxylate | 95533-03-2

• 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-benzyl-5-ethyl-2-(1H-indol-3-yl)piperidine-4-carboxylate
• CAS: 95533-03-2
• 化学式: C₂₄H₂₈N₂O₂
• 分子量: 376.499
• InChiKey: FNEGBSVTINNFNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 1-benzyl-5-ethyl-2-(1H-indol-3-yl)piperidine-4-carboxylate 在 palladium dihydroxide barium dihydroxide 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 dimethyl(methylthio)sulfonium tetrafluoroborate 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 67.0h， 生成 6α-(methylthio)-20-epitubifoline
  参考文献：
  名称：

  A new synthetic entry to pentacyclic Strychnos alkaloids. Total synthesis of (.+-.)-tubifolidine, (.+-.)-tubifoline, and (.+-.)-19,20-dihydroakuammicine

  摘要：

  A new strategy for the synthesis of pentacyclic Strychnos alkaloids has been developed. It consists in the closure of the five-membered E ring by cyclization upon the indole 3-position from a suitably N-substituted tetracyclic system embodying rings ABCD of the alkaloids. Attempts to effect the key cyclization either by Pummerer rearrangement of sulfinylacetamides 4 and 6, from chloroacetamide 12, or from bis(methylthio)acetamide 10b (exocyclic amide carbonyl group) resulted in failure. In the first case dithioacetals 9 and 10, respectively, were formed in good yields. Cyclization from alcohol 13 or from the indole-deactivated acetal 15 and dithiocetal 18 were also unsuccessful: noncyclized products coming from the initially formed oxonium or thionium intermediates 16 were obtained. Cyclization was satisfactorily accomplished in 49% yield by treatment of the N-unsubstituted indole dithioacetal 23 with DMTSF. The resulting pentacycle 25 was converted to 20-deethyltubifolidine (27). A similar treatment from dithioacetal 41a, prepared from the secondary amine 32a, afforded pentacycle 42a, from which the alkaloids tubifoline, tubifolidine, and 19,20-dihydroakuammicine were synthesized.

  DOI：

  10.1021/jo00313a017

文献信息

• A new strategy for the synthesis of pentacyclic Strychnos alkaloids: synthesis of (±)-tubifolidine
  作者：Mercedes Amat、Ana Linares、M.-Luisa Salas、Mercedes Alvarez、Joan Bosch

  DOI：10.1039/c39880000420

  日期：——

  The hexahydro-1,5-methanoazocino[4,3-b]indole (2a) was converted into (±)-tubifolidine (6a)via a four-step synthetic sequence which involves cyclization of a thionium ion upon the 3-position of a 2,3-disubstituted indole as the crucial step.

  通过四步合成序列将六氢-1,5-甲亚氮并吲哚并[4,3- b ]吲哚（2a）转化为（±）-tubifolidine（6a），该过程涉及在硫醇离子的3位上环化硫鎓离子。 2,3-二取代的吲哚是关键步骤。
• AMAT, MERCEDES;LINARES, ANA;SALAS, M. -LUISA;ALVAREZ, MERCEDES;BOSCH, JOA+, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 6, 420-421
  作者：AMAT, MERCEDES、LINARES, ANA、SALAS, M. -LUISA、ALVAREZ, MERCEDES、BOSCH, JOA+

  DOI：——

  日期：——