α-(acetyl-methyl-amino)-isobutyric acid | 190602-97-2

• 英文名称: α-(acetyl-methyl-amino)-isobutyric acid
• 英文别名: α-(Acetyl-methyl-amino)-isobuttersaeure；2-methyl-2-(N-methylacetamido)propanoic acid；2-[acetyl(methyl)amino]-2-methylpropanoic acid
• CAS: 190602-97-2
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: ZUGVBQSJDWCALN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Ac-NMeAib-Phe-OMe 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 生成 α-(acetyl-methyl-amino)-isobutyric acid
  参考文献：
  名称：

  Mechanistic Studies of an Unusual Amide Bond Scission

  摘要：

  Unusual acid cleavage reactions are reported for derivatives containing acylated N-methyl-alpha-aminoisobutyryl (NMeAib) residues. The bond linking the NMeAib residue to the following amino acid is cleaved. Through X-ray diffraction studies of the NMeAib containing molecules, we have shown that the carbonyl oxygen atom of the preceding residue is in proximity to the carbonyl carbon of the NMeAib residue. Thus, it can act as an internal nucleophile leading to a cleavage reaction by way of an oxazolinium ion intermediate. Kinetic experiments for the cleavage reaction were carried out on a series of benzoyl dipeptide derivatives (p-X-C6H4C(O)-NMeAib-Phe-OMe) where X is varied from NO2 to Cl. The value of rho = -1.335 for the Hammett linear free-energy relationship strongly supports the intermolecular oxazolinium intermediate proposed.

  DOI：

  10.1021/ja9913131

文献信息

• [EN] CRF RECEPTOR ANTAGONISTS AND METHODS OF USE<br/>[FR] ANTAGONISTES DU RÉCEPTEUR CRF ET MÉTHODES D'UTILISATION
  申请人：NEUROCRINE BIOSCIENCES INC

  公开号：WO2021062246A1

  公开（公告）日：2021-04-01

  Compounds are provided herein, as well as related preparations, compositions and methods for treating diseases and/or disorders that would benefit from the same such as congenital adrenal hyperplasia (CAH).

  本文提供了化合物，以及相关的制剂、组合物和治疗方法，用于治疗需要这些治疗的疾病和/或疾病，例如先天性肾上腺皮质增生症（CAH）。
• Steiger, Helvetica Chimica Acta, 1934, vol. 17, p. 579
  作者：Steiger

  DOI：——

  日期：——