(5R,6S)-(tert-butyl) 5-hydroxy-4-oxo-6-phenyl-3-[(S)-1-phenylethyl]-3,4,5,6-tetrahydro-1H-azocino[5,4-b]indole-7(2H)-carboxylate | 1431767-79-1

• 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: (5R,6S)-(tert-butyl) 5-hydroxy-4-oxo-6-phenyl-3-[(S)-1-phenylethyl]-3,4,5,6-tetrahydro-1H-azocino[5,4-b]indole-7(2H)-carboxylate
• 英文别名: tert-butyl (5R,6S)-5-hydroxy-4-oxo-6-phenyl-3-[(1S)-1-phenylethyl]-1,2,5,6-tetrahydroazocino[5,4-b]indole-7-carboxylate
• CAS: 1431767-79-1
• 化学式: C₃₂H₃₄N₂O₄
• 分子量: 510.633
• InChiKey: BKSNCFCEIUBFQH-DGYBNRFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R,6S)-(tert-butyl) 5-hydroxy-4-oxo-6-phenyl-3-[(S)-1-phenylethyl]-3,4,5,6-tetrahydro-1H-azocino[5,4-b]indole-7(2H)-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以80%的产率得到(5R,6S)-5-hydroxy-6-phenyl-3-[(S)-1-phenylethyl]-2,3,5,6-tetrahydro-1H-azocino[5,4-b]indol-4(7H)-one
  参考文献：
  名称：

  The Use of Sodium Chlorite in the Direct Synthesis of Glycidic Amides: Enantiopure Synthesis of Both Enantiomers of Norbalasubramide

  摘要：

  Recently, the first direct method for preparing 2,3-epoxyamides (glycidic amides) was disclosed. Now in this letter, the enantiopure synthesis of both enantiomers of norbalasubramide featuring this synthetic method is reported. To this end, chiral N-allyltryptamine 12 was prepared and transformed into an inseparable mixture of diastereomeric epoxyamides 13a/13b, which were submitted to intramolecular cyclization with Cu(OTf)(2) to afford a separable mixture of eight-membered ring lactams 14a and 14b. Finally, after removal of the protective group and the chiral auxiliary an enantiopure synthesis of the title compounds was completed.

  DOI：

  10.1055/s-0032-1316893
• 作为产物：
  描述：

  3-(2-溴乙基)吲哚 在 4-二甲氨基吡啶 、 sodium dihydrogenphosphate dihydrate 、 copper(II) bis(trifluoromethanesulfonate) 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 14.75h， 生成 (5R,6S)-(tert-butyl) 5-hydroxy-4-oxo-6-phenyl-3-[(S)-1-phenylethyl]-3,4,5,6-tetrahydro-1H-azocino[5,4-b]indole-7(2H)-carboxylate
  参考文献：
  名称：

  The Use of Sodium Chlorite in the Direct Synthesis of Glycidic Amides: Enantiopure Synthesis of Both Enantiomers of Norbalasubramide

  摘要：

  Recently, the first direct method for preparing 2,3-epoxyamides (glycidic amides) was disclosed. Now in this letter, the enantiopure synthesis of both enantiomers of norbalasubramide featuring this synthetic method is reported. To this end, chiral N-allyltryptamine 12 was prepared and transformed into an inseparable mixture of diastereomeric epoxyamides 13a/13b, which were submitted to intramolecular cyclization with Cu(OTf)(2) to afford a separable mixture of eight-membered ring lactams 14a and 14b. Finally, after removal of the protective group and the chiral auxiliary an enantiopure synthesis of the title compounds was completed.

  DOI：

  10.1055/s-0032-1316893

文献信息

• Synthesis of the indoloazocine derivatives from a chiral indol amide-stabilized sulfur ylide
  作者：Maira Juárez-Calderón、David M. Aparicio、Dino Gnecco、Jorge R. Juárez、Laura Orea、Angel Mendoza、Fernando Sartillo-Piscil、Esther del Olmo、Joel L. Terán

  DOI：10.1016/j.tetlet.2013.03.068

  日期：2013.5

  We present here a synthetic route for the access to a series of diverse indoloazocine derivatives through selective epoxidation of chiral sulfonium salt 4, which reacts with diverse aromatic and aliphatic aldehydes to give trans-glycidic amides, followed by an intramolecular electrophilic aromatic substitution promoted by Cu(OTf)(2) giving the desired heterocyclic compound in a high chemical yield. Using this strategy, the total synthesis of (S,R)-(+)-norbalasubramide was achieved. (c) 2013 Elsevier Ltd. All rights reserved.