N-(3,4-dimethoxybenzyl)alanine methyl ester | 187085-94-5

• 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-(3,4-dimethoxybenzyl)alanine methyl ester
• 英文别名: Methyl 2-[(3,4-dimethoxyphenyl)methylamino]propanoate
• CAS: 187085-94-5
• 化学式: C₁₃H₁₉NO₄
• mdl: MFCD13473015
• 分子量: 253.298
• InChiKey: PFYKRTWJBWUKNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3,4-dimethoxybenzyl)alanine methyl ester 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 2-[(3,4-Dimethoxyphenyl)methyl-(5-oxo-7-trimethylsilylhept-6-ynoyl)amino]propanoic 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：

  2-溴丙酸甲酯 、 3,4-二甲氧基苄胺 以 四氢呋喃 为溶剂， 反应 24.0h， 以90%的产率得到N-(3,4-dimethoxybenzyl)alanine methyl ester
  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.