3-[N-(4-甲基苯基)氨基]丁酸乙酯 | 100618-27-7

• 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
• 中文名称: 3-[N-(4-甲基苯基)氨基]丁酸乙酯
• 英文名称: ethyl 3-[N-(4-methylphenyl)amino]butanoate
• 英文别名: Ethyl 3-p-toluidinobutyrate；3-p-toluidino-butyric acid ethyl ester；3-p-Toluidino-buttersaeure-aethylester；β-p-Toluidino-buttersaeure-aethylester；Ethyl 3-(4-methylanilino)butanoate
• CAS: 100618-27-7
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: YYKAEYKYACRTMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[N-(4-甲基苯基)氨基]丁酸乙酯 在 二硫化碳 、 五氯化磷 作用下， 生成 2,6-dimethyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-quinolin-4-one
  参考文献：
  名称：

  The Alkaloids of Tabernanthe iboga. Part VI.¹ The Synthesis of the Selenium Dehydrogenation Products from Ibogamine

  摘要：

  DOI：

  10.1021/ja01542a035
• 作为产物：
  描述：

  (Z)-ethyl 3-(p-tolylamino)but-2-enoate 在 三乙酰氧基硼氢化钠 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以65%的产率得到3-[N-(4-甲基苯基)氨基]丁酸乙酯
  参考文献：
  名称：

  Chemo- and Diastereoselective Reduction of .beta.-Enamino Esters: A Convenient Synthesis of Both cis- and trans-.gamma.-Amino Alcohols and .beta.-Amino Esters

  摘要：

  Convenient procedures for the chemo- and diastereoselective reduction of beta-enamino esters 1 are described. Both cis- and trans-gamma-amino alcohols 2 or beta-amino esters 3 can be prepared by reduction of beta-enamino esters 1, readily available starting materials, with the use of inexpensive reagents Nali-PrOH or NaHbB(OAc)(3)/AcOH, respectively, and the appropriate reduction conditions. The mechanisms and diastereoselectivities for the reductions are discussed. The relative configurations and conformations of the diastereoisomeric gamma-amino alcohols 2 and beta-amino esters 3 obtained are established by H-1 and C-13 NMR study and unequivocally set by their cyclic derivatives tetrahydro-1,3-oxazines 4.

  DOI：

  10.1021/jo00097a039

文献信息

• A one-pot synthesis of N-alkylaminobenzenes from nitroaromatics: reduction followed by reductive amination using B10H14
  作者：Jong Woo Bae、Young Jin Cho、Seung Hwan Lee、Choon-Ock Maing Yoon、Cheol Min Yoon

  DOI：10.1039/b005194m

  日期：——

  N-Alkylaminobenzenes were prepared in a simple and efficient one-pot synthesis by reduction of nitrobenzenes followed by reductive amination with decaborane (B10H14) in the presence of 10% Pd/C.

  通过还原硝基苯并随后在10% Pd/C存在下与癸硼烷（B10H14）进行还原胺化，简单高效地实现了N-烷基氨基苯的一锅法合成。
• Synthesis of Indole-3-carboxylic Acid Derivatives by Pd(0)-Catalyzed Intramolecular α-Arylation of β-(2-Iodoanilino) Esters
  作者：Daniel Solé、Olga Serrano

  DOI：10.1021/jo800034m

  日期：2008.3.1

  beta-(2-Iodoanilino) esters undergo intramolecular alpha-arylation in the presence of Pd(PPh3)(4) and potassium phenoxide. The reaction is a useful methodology for the preparation of indole-3-carboxylic acid ester derivatives.
• The Alkaloids of Tabernanthe iboga. Part VI.¹ The Synthesis of the Selenium Dehydrogenation Products from Ibogamine
  作者：H. B. MacPhillamy、R. L. Dziemian、R. A. Lucas、M. E. Kuehne

  DOI：10.1021/ja01542a035

  日期：1958.5
• Chemo- and Diastereoselective Reduction of .beta.-Enamino Esters: A Convenient Synthesis of Both cis- and trans-.gamma.-Amino Alcohols and .beta.-Amino Esters
  作者：Giuseppe Bartoli、Cristina Cimarelli、Enrico Marcantoni、Gianni Palmieri、Marino Petrini

  DOI：10.1021/jo00097a039

  日期：1994.9

  Convenient procedures for the chemo- and diastereoselective reduction of beta-enamino esters 1 are described. Both cis- and trans-gamma-amino alcohols 2 or beta-amino esters 3 can be prepared by reduction of beta-enamino esters 1, readily available starting materials, with the use of inexpensive reagents Nali-PrOH or NaHbB(OAc)(3)/AcOH, respectively, and the appropriate reduction conditions. The mechanisms and diastereoselectivities for the reductions are discussed. The relative configurations and conformations of the diastereoisomeric gamma-amino alcohols 2 and beta-amino esters 3 obtained are established by H-1 and C-13 NMR study and unequivocally set by their cyclic derivatives tetrahydro-1,3-oxazines 4.