Z-(Me)Aib-OMe | 445396-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Z-(Me)Aib-OMe
• CAS: 445396-26-9
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: DBGYLCIAOKXRTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Z-(Me)Aib-OMe 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以100%的产率得到H-(Me)Aib-OMe*HBr
  参考文献：
  名称：

  Synthesis and Use of 2H-Azirin-3-amines as Dipeptide Synthons

  摘要：

  The synthesis of the new 2H-azirin-3-amines ('3-amino-2H-azirines') 11, 20, 28, and 33 as dipeptide synthons is described. The reactions of the starting amides with Lawesson reagent gave the corresponding thioamides, and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to the desired products. It is shown that these 2H-azirin-3-amines can conveniently be used as building blocks of the dipeptides Aib-(Me)Axx (Axx = alanine, valine), Aib-Homoproline, and Iva-Pro in the synthesis of several model peptides. However, some limitations apply for the synthesis of such 2H-azirin-3-amines. The starting material for the azirine synthesis, the corresponding thioamides, cannot generally be synthesized, and the 2H-azirin-3-amines could not be obtained in all cases from the thioamides prepared.

  DOI：

  10.1002/1522-2675(200203)85:3<885::aid-hlca885>3.0.co;2-z
• 作为产物：
  描述：

  N-苄氧羰酰基-2-甲基丙氨酸 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 以96%的产率得到Z-(Me)Aib-OMe
  参考文献：
  名称：

  Synthesis and Use of 2H-Azirin-3-amines as Dipeptide Synthons

  摘要：

  The synthesis of the new 2H-azirin-3-amines ('3-amino-2H-azirines') 11, 20, 28, and 33 as dipeptide synthons is described. The reactions of the starting amides with Lawesson reagent gave the corresponding thioamides, and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to the desired products. It is shown that these 2H-azirin-3-amines can conveniently be used as building blocks of the dipeptides Aib-(Me)Axx (Axx = alanine, valine), Aib-Homoproline, and Iva-Pro in the synthesis of several model peptides. However, some limitations apply for the synthesis of such 2H-azirin-3-amines. The starting material for the azirine synthesis, the corresponding thioamides, cannot generally be synthesized, and the 2H-azirin-3-amines could not be obtained in all cases from the thioamides prepared.

  DOI：

  10.1002/1522-2675(200203)85:3<885::aid-hlca885>3.0.co;2-z

文献信息

• Synthesis of N-alkyl-Cα,α-dimethylglycine derivatives
  作者：Luís S. Monteiro、Silvia M.M.A. Pereira-Lima、Sofia Pereira、João N. Machado

  DOI：10.3998/ark.5550190.p008.622

  日期：——

  Foundation for Science and Technology (FCT) – Portugal and Fundo Europeu de Desenvolvimento Regional (FEDER) for financial support to Chemistry Centre of University of Minho. The NMR spectrometer Bruker Avance II+ 400 is part of the National NMR Network and was purchased in the framework of the National Program for Scientific Re-equipment; contract REDE/1517/RMN/2005, with funds from POCI 2010, FEDER

  科学技术基金会 (FCT) – 葡萄牙和欧洲发展基金会 (FEDER) 为米尼奥大学化学中心提供财政支持。NMR 波谱仪 Bruker Avance II+ 400 是 National NMR Network 的一部分，是在 National Program for Scientific Re-equipment 的框架内购买的；合同 REDE/1517/RMN/2005，资金来自 POCI 2010、FEDER 和 FCT。