(S)-2-Amino-3-(12H-pyrido[1,2-a;3,4-b']diindol-13-yl)-propionic acid | 253448-65-6

• 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: (S)-2-Amino-3-(12H-pyrido[1,2-a;3,4-b']diindol-13-yl)-propionic acid
• 英文别名: (2S)-2-amino-3-(3,13-diazapentacyclo[11.7.0.02,10.04,9.014,19]icosa-1(20),2(10),4,6,8,11,14,16,18-nonaen-20-yl)propanoic acid
• CAS: 253448-65-6
• 化学式: C₂₁H₁₇N₃O₂
• 分子量: 343.385
• InChiKey: NTJLQUUZGFVOLP-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-3-(12H-pyrido[1,2-a;3,4-b']diindol-13-yl)-propionic acid 在 三氯化铁 作用下， 以 水 、 xylene 为溶剂， 以23%的产率得到homofascaplysin C
  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：

  (S)-2-Acetylamino-3-[3'-((S)-2-acetylamino-2-methoxycarbonyl-ethyl)-1H,1'H-[2,2']biindolyl-3-yl]-propionic acid methyl ester 在 盐酸 、 lithium hydroxide 、 sodium hydroxide 、 1-羟基苯并三唑 、 溶剂黄146 、 乙酰氯 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 43.67h， 生成 (S)-2-Amino-3-(12H-pyrido[1,2-a;3,4-b']diindol-13-yl)-propionic acid
  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.