3-Methyl-5-oxo-7-trimethylsilylhept-6-ynoic acid | 187085-85-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-Methyl-5-oxo-7-trimethylsilylhept-6-ynoic acid
• CAS: 187085-85-4
• 化学式: C₁₁H₁₈O₃Si
• 分子量: 226.348
• InChiKey: DSXRKIYSODHNGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Methyl-5-oxo-7-trimethylsilylhept-6-ynoic acid 在 N-甲基吗啉 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 、 lithium iodide 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 (2S)-1-(3-methyl-5-oxo-7-trimethylsilylhept-6-ynoyl)pyrrolidine-2-carboxylic acid
  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
• 作为产物：
  描述：

  3-甲基戊二酸酐 、 二(三甲基甲硅烷基)乙炔 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到3-Methyl-5-oxo-7-trimethylsilylhept-6-ynoic acid
  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

• 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.