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 | 253448-74-7

• 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: 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
• CAS: 253448-74-7
• 化学式: C₂₅H₂₄N₄O₄
• 分子量: 444.49
• InChiKey: GRDGTAWQXSXMPC-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  N^α-Ac-L-Trp-D-Trp-OMe 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 17.0h， 以55%的产率得到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
  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