N-[(12S,15S)-12-(tert-butylcarbamoylamino)-14-oxo-3,13,24-triazapentacyclo[15.7.0.02,10.04,9.018,23]tetracosa-1(17),2(10),4,6,8,18,20,22-octaen-15-yl]acetamide | 253448-76-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(12S,15S)-12-(tert-butylcarbamoylamino)-14-oxo-3,13,24-triazapentacyclo[15.7.0.02,10.04,9.018,23]tetracosa-1(17),2(10),4,6,8,18,20,22-octaen-15-yl]acetamide
• CAS: 253448-76-9
• 化学式: C₂₈H₃₂N₆O₃
• 分子量: 500.6
• InChiKey: FLBGBKMDJOUIES-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  131
• 氢给体数：
  6
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(12S,15S)-12-(tert-butylcarbamoylamino)-14-oxo-3,13,24-triazapentacyclo[15.7.0.02,10.04,9.018,23]tetracosa-1(17),2(10),4,6,8,18,20,22-octaen-15-yl]acetamide 在 三氟乙酸 作用下， 反应 15.0h， 以10%的产率得到(S)-2-Acetylamino-3-(12H-pyrido[1,2-a;3,4-b']diindol-13-yl)-propionamide
  参考文献：
  名称：

  Synthesis of Homofascaplysin C and Indolo[2,3-a]carbazole from Ditryptophans

  摘要：

  The 2,2'-biindole core of ditryptophan cross-links is prominent in the fascaplysins and the indolocarbazole glycoside natural products. N-Acyliminium ions derived from the C-terminus of ditryptophan peptides cyclize in one of two modes: N-alkylation or C-alkylation. The surrounding peptide offers some control over the course of the cyclization and allows the preparation of homofascaplysin C or indolo[2,3-alpha]carbazole. These targets are modest, but they are generated through carbocyclic intermediates rich in stereochemistry, and decidedly non-peptide in character.

  DOI：

  10.1021/jo9909249
• 作为产物：
  描述：

  methyl (12R,15S)-15-acetamido-14-oxo-3,13,24-triazapentacyclo[15.7.0.02,10.04,9.018,23]tetracosa-1(17),2(10),4,6,8,18,20,22-octaene-12-carboxylate 在 盐酸 、 肼 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 20.5h， 生成 N-[(12S,15S)-12-(tert-butylcarbamoylamino)-14-oxo-3,13,24-triazapentacyclo[15.7.0.02,10.04,9.018,23]tetracosa-1(17),2(10),4,6,8,18,20,22-octaen-15-yl]acetamide
  参考文献：
  名称：

  Synthesis of Homofascaplysin C and Indolo[2,3-a]carbazole from Ditryptophans

  摘要：

  The 2,2'-biindole core of ditryptophan cross-links is prominent in the fascaplysins and the indolocarbazole glycoside natural products. N-Acyliminium ions derived from the C-terminus of ditryptophan peptides cyclize in one of two modes: N-alkylation or C-alkylation. The surrounding peptide offers some control over the course of the cyclization and allows the preparation of homofascaplysin C or indolo[2,3-alpha]carbazole. These targets are modest, but they are generated through carbocyclic intermediates rich in stereochemistry, and decidedly non-peptide in character.

  DOI：

  10.1021/jo9909249

文献信息

• Synthesis of Homofascaplysin C and Indolo[2,3-<i>a</i>]carbazole from Ditryptophans
  作者：David S. Carter、David L. Van Vranken

  DOI：10.1021/jo9909249

  日期：1999.11.1

  The 2,2'-biindole core of ditryptophan cross-links is prominent in the fascaplysins and the indolocarbazole glycoside natural products. N-Acyliminium ions derived from the C-terminus of ditryptophan peptides cyclize in one of two modes: N-alkylation or C-alkylation. The surrounding peptide offers some control over the course of the cyclization and allows the preparation of homofascaplysin C or indolo[2,3-alpha]carbazole. These targets are modest, but they are generated through carbocyclic intermediates rich in stereochemistry, and decidedly non-peptide in character.