N-methyl-N-(2,2-diethoxyethyl)aniline | 32431-43-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-methyl-N-(2,2-diethoxyethyl)aniline
• 英文别名: (N-Methyl-N-phenyl-amino)-acetaldehyd-diaethylacetal；N-Methyl-N-phenylaminoacetal；N-(2,2-diethoxyethyl)-N-methylaniline
• CAS: 32431-43-9
• 化学式: C₁₃H₂₁NO₂
• mdl: MFCD18848380
• 分子量: 223.315
• InChiKey: MSHBPVQTBOBZJM-UHFFFAOYSA-N

物化性质

• 沸点：
  150-152 °C(Press: 13 Torr)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methyl-N-(2,2-diethoxyethyl)aniline 在 propylsulfonic acid-functionalized silica 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以96%的产率得到1-甲基吲哚
  参考文献：
  名称：

  General and efficient synthesis of 2,3-unsubstituted indoles catalyzed by acidic mesoporous molecular sieves

  摘要：

  A general and efficient method for the synthesis of 2,3-unsubstituted indoles has been established by the intramolecular cyclization of N-benzyl 2-anilinoacetals. Acidic mesoporous molecular sieve (MCM-41-SO3H) has shown excellent catalytic activity on this transformation, and the 2,3-unsubstituted indoles bearing 7-substituent or strong electron-withdrawing substituents also could be achieved by this protocol. Moreover, the heterogeneous catalyst, MCM-41-SO3H, could be conveniently recovered and reused without obvious loss of the catalytic activity. This work will provide an economic and environmental-benign method for the construction of various indole derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.026
• 作为产物：
  描述：

  2-溴-1,1-二乙氧基乙烷 、 N-甲基苯胺 生成 N-methyl-N-(2,2-diethoxyethyl)aniline
  参考文献：
  名称：

  在三氟乙酸酐中使用三氟化硼通过改进的Pomeranz-Fritsch反应合成异喹啉，吲哚和苯并噻吩

  摘要：

  据报道，使用一种新的三氟化硼-三氟乙酸酐试剂进行了Pomeranz-Fritsch环化反应。带有7-OMe基团的异喹啉已经以高收率制备，并且该方法扩展到由相应的缩醛形成N-取代的吲哚和苯并噻吩。用这种方法不能得到苯并呋喃，也不能诱导Bischler-Napieralski型环化反应。在后一种情况下，当适当活化时，起始酰胺的芳环被乙酰化。

  DOI：

  10.1016/s0040-4020(01)90874-9

文献信息

• BOBBITT J. M.; BOURQUE A. J., HETEROCYCLES, 35,(1987) SPEC. ISSUE, 601-616
  作者：BOBBITT J. M.、 BOURQUE A. J.

  DOI：——

  日期：——
• General and efficient synthesis of 2,3-unsubstituted indoles catalyzed by acidic mesoporous molecular sieves
  作者：Nan Sun、Lingfen Hong、Fang Huang、Hong Ren、Weimin Mo、Baoxiang Hu、Zhenlu Shen、Xinquan Hu

  DOI：10.1016/j.tet.2013.03.026

  日期：2013.5

  A general and efficient method for the synthesis of 2,3-unsubstituted indoles has been established by the intramolecular cyclization of N-benzyl 2-anilinoacetals. Acidic mesoporous molecular sieve (MCM-41-SO3H) has shown excellent catalytic activity on this transformation, and the 2,3-unsubstituted indoles bearing 7-substituent or strong electron-withdrawing substituents also could be achieved by this protocol. Moreover, the heterogeneous catalyst, MCM-41-SO3H, could be conveniently recovered and reused without obvious loss of the catalytic activity. This work will provide an economic and environmental-benign method for the construction of various indole derivatives. (C) 2013 Elsevier Ltd. All rights reserved.
• The synthesis of isoquinolines, indoles and benzthiophen by an improved Pomeranz-Fritsch reaction, using boron trifluoride in trifluoroacetic anhydride
  作者：M.J. Bevis、E.J. Forbes、N.N. Naik、B.C. Uff

  DOI：10.1016/s0040-4020(01)90874-9

  日期：1971.1

  Pomeranz-Fritsch cyclisations are reported using a new reagent boron trifluoride-trifluoroacetic anhydride. Isoquinolines carrying 7-OMe groups have been prepared in good yields and the method extended to the formation of N-substituted indoles and of benzthiophen from the corresponding acetals. Benzofuran could not be obtained by this procedure nor could a Bischler-Napieralski type cyclisation be induced

  据报道，使用一种新的三氟化硼-三氟乙酸酐试剂进行了Pomeranz-Fritsch环化反应。带有7-OMe基团的异喹啉已经以高收率制备，并且该方法扩展到由相应的缩醛形成N-取代的吲哚和苯并噻吩。用这种方法不能得到苯并呋喃，也不能诱导Bischler-Napieralski型环化反应。在后一种情况下，当适当活化时，起始酰胺的芳环被乙酰化。