Methyl 2-[2-(4-nitrophenyl)ethyl-(5-oxo-7-trimethylsilylhept-6-ynoyl)amino]propanoate | 187085-65-0

• 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 2-[2-(4-nitrophenyl)ethyl-(5-oxo-7-trimethylsilylhept-6-ynoyl)amino]propanoate
• CAS: 187085-65-0
• 化学式: C₂₂H₃₀N₂O₆Si
• 分子量: 446.575
• InChiKey: WYKVPZZFVAMRHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2-[2-(4-nitrophenyl)ethyl-(5-oxo-7-trimethylsilylhept-6-ynoyl)amino]propanoate 在 lithium iodide 作用下， 以 乙酸乙酯 为溶剂， 生成 2-[2-(4-Nitrophenyl)ethyl-(5-oxo-7-trimethylsilylhept-6-ynoyl)amino]propanoic acid
  参考文献：
  名称：

  通过新颖的分子内1,3-偶极环加成方法轻松合成4-氧代-4,5,6,7-四氢吲哚

  摘要：

  使用新的分子内1,3-偶极环加成方法可分两步实现4-酮-4,5,6,7-四氢吲哚6-12的一般合成，产率中等（45-60％）。这种方法的潜力通过丝裂霉素骨架（15）和拓扑异构酶-1抑制剂骨架（17）的合成得到证明。

  DOI：

  10.1016/0040-4039(96)00426-1
• 作为产物：
  描述：

  4-硝基苯乙胺盐酸盐 在 N-甲基吗啉 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 、 氨 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 48.33h， 生成 Methyl 2-[2-(4-nitrophenyl)ethyl-(5-oxo-7-trimethylsilylhept-6-ynoyl)amino]propanoate
  参考文献：
  名称：

  New Approach for the General Synthesis of Oxotetrahydroindoles via Intramolecular Cycloadditions of Azomethine Ylides with Tethered Alkynes

  摘要：

  A new method for the synthesis of oxotetrahydroindoles has been achieved employing an intramolecular dipolar cycloaddition approach involving mesoionic species (munchnones) with electron-deficient alkynes. The methodology is quite general and convergent as shown by the synthesis of a variety of tri- and tetrasubstituted oxotetrahydroindoles 18, 21, 24, 27, 30, and 34. LiI-based ester cleavage in the presence of an electrophilic acetylenic ketone was critical for formation of the requisite cycloaddition substrates. The cycloaddition is virtually unaffected by the presence of gem-dimethyl groups in the side chain (cf. 38). The presence of a substituted benzyl or a phenethyl moiety on nitrogen, a polarized acetylene, and an appropriate tether between dipole and dipolarophile are essential for obtaining optimal efficiency.

  DOI：

  10.1021/jo9614598

文献信息

• A simple and general synthesis of 4-oxo-4,5,6,7-tetrahydroindoles via a novel intramolecular 1,3-dipolar cycloaddition approach
  作者：Darrell R. Hutchison、Naresh K. Nayyar、Michael J. Martinelli

  DOI：10.1016/0040-4039(96)00426-1

  日期：1996.4

  A general synthesis of 4-keto-4,5,6,7-tetrahydroindoles 6–12 has been achieved in two steps using a new intramolecular 1,3-dipolar cycloaddition approach in moderate yields (45–60%). The potential of this methodology is demonstrated by the synthesis of a mitomycin skeleton (15) and a topoisomerase-1 inhibitor skeleton (17).

  使用新的分子内1,3-偶极环加成方法可分两步实现4-酮-4,5,6,7-四氢吲哚6-12的一般合成，产率中等（45-60％）。这种方法的潜力通过丝裂霉素骨架（15）和拓扑异构酶-1抑制剂骨架（17）的合成得到证明。
• New Approach for the General Synthesis of Oxotetrahydroindoles via Intramolecular Cycloadditions of Azomethine Ylides with Tethered Alkynes
  作者：Naresh K. Nayyar、Darrell R. Hutchison、Michael J. Martinelli

  DOI：10.1021/jo9614598

  日期：1997.2.1

  A new method for the synthesis of oxotetrahydroindoles has been achieved employing an intramolecular dipolar cycloaddition approach involving mesoionic species (munchnones) with electron-deficient alkynes. The methodology is quite general and convergent as shown by the synthesis of a variety of tri- and tetrasubstituted oxotetrahydroindoles 18, 21, 24, 27, 30, and 34. LiI-based ester cleavage in the presence of an electrophilic acetylenic ketone was critical for formation of the requisite cycloaddition substrates. The cycloaddition is virtually unaffected by the presence of gem-dimethyl groups in the side chain (cf. 38). The presence of a substituted benzyl or a phenethyl moiety on nitrogen, a polarized acetylene, and an appropriate tether between dipole and dipolarophile are essential for obtaining optimal efficiency.