N-Phth-Trp-Gly-O-pClPh | 1508263-21-5

• 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-Phth-Trp-Gly-O-pClPh
• 英文别名: (4-chlorophenyl) 2-[[(2S)-2-(1,3-dioxoisoindol-2-yl)-3-(1H-indol-3-yl)propanoyl]amino]acetate
• CAS: 1508263-21-5
• 化学式: C₂₇H₂₀ClN₃O₅
• 分子量: 501.926
• InChiKey: LZZWUSLFUTZXSM-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Phth-Trp-Gly-O-pClPh 在 碳酸氢钠 、 Selectfluor 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以60.784%的产率得到
  参考文献：
  名称：

  Double Annulative Cascade of Tryptophan-Containing Peptides Triggered by Selectfluor

  摘要：

  A common dearomative strategy toward the kapakahines B/F and chaetominine natural products is reported. The proposed biomimetic strategy generates the tetracyclic alpha-carboline core in a single step, featuring a selectfluor-mediated dearomatization of preactivated N-Phth-Trp-Xaa-OR dipeptides at the C-terminus. The pivotal cascade includes a double annulation and the formation of three carbon-heteroatom bonds while gaining, for the first time, some insight on the diastereoselectivity outcome during the formation of the alpha-carboline fragment.

  DOI：

  10.1021/ol403281t
• 作为产物：
  描述：

  N-酞酰-L-色氨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 氘代四氢呋喃 、 水 为溶剂， 反应 42.0h， 生成 N-Phth-Trp-Gly-O-pClPh
  参考文献：
  名称：

  Double Annulative Cascade of Tryptophan-Containing Peptides Triggered by Selectfluor

  摘要：

  A common dearomative strategy toward the kapakahines B/F and chaetominine natural products is reported. The proposed biomimetic strategy generates the tetracyclic alpha-carboline core in a single step, featuring a selectfluor-mediated dearomatization of preactivated N-Phth-Trp-Xaa-OR dipeptides at the C-terminus. The pivotal cascade includes a double annulation and the formation of three carbon-heteroatom bonds while gaining, for the first time, some insight on the diastereoselectivity outcome during the formation of the alpha-carboline fragment.

  DOI：

  10.1021/ol403281t

文献信息

• Double Annulative Cascade of Tryptophan-Containing Peptides Triggered by Selectfluor
  作者：Bret Tréguier、Stéphane P. Roche

  DOI：10.1021/ol403281t

  日期：2014.1.3

  A common dearomative strategy toward the kapakahines B/F and chaetominine natural products is reported. The proposed biomimetic strategy generates the tetracyclic alpha-carboline core in a single step, featuring a selectfluor-mediated dearomatization of preactivated N-Phth-Trp-Xaa-OR dipeptides at the C-terminus. The pivotal cascade includes a double annulation and the formation of three carbon-heteroatom bonds while gaining, for the first time, some insight on the diastereoselectivity outcome during the formation of the alpha-carboline fragment.