(l)-3-(Benzoylamino)-2-methylbuttersaeure-methylester | 112979-44-9

• 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: (l)-3-(Benzoylamino)-2-methylbuttersaeure-methylester
• 英文别名: methyl (2R,3R)-3-benzamido-2-methylbutanoate
• CAS: 112979-44-9；112979-52-9；121054-38-4；139344-73-3；147126-18-9
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: BYZNUXXGADAARK-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (l)-3-(Benzoylamino)-2-methylbuttersaeure-methylester 在 sodium hexamethyldisilazane 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 (4S,5R)-4,5-Dimethyl-2-phenyl-4,5-dihydro-oxazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  A facile and stereocontrolled synthesis of syn-α-alkyl α-hydroxy β-amino acids

  摘要：

  The diastereoselective synthesis of syn-alpha-alkyl alpha-hydroxy beta-amino acids 4a-h was easily accomplished by reaction of the sodium dianion of the corresponding anti alpha-alkyl beta-benzoylamino acid methyl eaters with iodine. The intermediate alpha-iodo derivatives spontaneously afforded cis-oxazolines which, upon hydrolysis, provided the desired products, with diastereoselectivities up to 99:1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01772-4
• 作为产物：
  描述：

  N-苯甲酰基-3-氨基丁酸 在 三甲基氯硅烷 作用下， 生成 (l)-3-(Benzoylamino)-2-methylbuttersaeure-methylester
  参考文献：
  名称：

  在2-位上的3-氨基丁酸非对映选择性烷基化†

  摘要：

  2位非对映选择性烷基化3-氨基丁酸

  DOI：

  10.1002/hlca.19880710724

文献信息

• Diastereoselektive Alkylierung von 3-Aminobutansäure in der 2-Stellung
  作者：Heinrich Estermann、Dieter Seebach

  DOI：10.1002/hlca.19880710724

  日期：1988.11.2

  Diastereoselective Alkylation 3-Aminobutanoic Acid in the 2-Position

  2位非对映选择性烷基化3-氨基丁酸
• Synthesis and Ring Opening of Methyl 2-Alkyl-3-(alkyl/aryl)-1-benzoylaziridine-2-carboxylates: Synthesis of Polysubstituted Amino Acids
  作者：Carmela Papa、Claudia Tomasini

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1569::aid-ejoc1569>3.0.co;2-x

  日期：2000.4

  A new method for the preparation of 2,2,3-trisubstituted methyl 1-benzoylaziridine-2-carboxylates is reported. These compounds have been obtained starting from α-alkyl β-amino acids by formation of the lithium dianion and reaction with iodine. The aziridines undergo ring expansion or ring opening, depending on the substituents of the aziridine ring and on the reaction conditions. Following these methods

  报道了一种制备 2,2,3-三取代甲基 1-benzoylaziridine-2-carboxylates 的新方法。这些化合物是从α-烷基β-氨基酸开始，通过形成锂二价阴离子并与碘反应获得的。氮丙啶会发生扩环或开环，这取决于氮丙啶环的取代基和反应条件。按照这些方法，已经合成了α-取代的α-羟基β-氨基酸和α-取代的β-羟基α-氨基酸。
• α-Alkylation of β-aminobutanoates with lk-1.2-induction
  作者：Dieter Seebach、Heinrich Estermann

  DOI：10.1016/s0040-4039(00)96296-8

  日期：1987.1
• Grassypeptolides A−C, Cytotoxic Bis-thiazoline Containing Marine Cyclodepsipeptides
  作者：Jason C. Kwan、Ranjala Ratnayake、Khalil A. Abboud、Valerie J. Paul、Hendrik Luesch

  DOI：10.1021/jo1013564

  日期：2010.12.3

  Grassypeptolides A-C (1-3), a group of closely related bis-thiazoline containing cyclic depsipeptides, have been isolated from extracts of the marine cyanobacterium Lyngbya confervoides. Although structural differences between the analogues are minimal, comparison of the in vitro cytotoxicity of the series revealed a structure-activity relationship. When the ethyl substituent of 1 is changed to a methyl substituent in 2, activity is only slightly reduced (3-4-fold), whereas inversion of the Phe unit flanking the bis-thiazoline moiety results in 16-23-fold greater potency. We show that both 1 and 3 cause G1 phase cell cycle arrest at lower concentrations, followed at higher concentrations by G2/M phase arrest, and that these compounds bind Cu2+. and Zn2+. The three-dimensional structure of 2 was determined by MS, NMR, and X-ray crystallography, and the structure of 3 was established by MS, NMR, and chemical degradation. The structure of 3 was explored by in silico molecular modeling, revealing subtle differences in overall conformation between 1 and 3. Attempts to interconvert 1 and 3 with base were unsuccessful, but enzymatic conversion may be possible and could be a novel form of activation for chemical defense.
• SEEBACH, D.;ESTERMANN, H., TETRAHEDRON LETT., 28,(1987) N 27, 3103-3106
  作者：SEEBACH, D.、ESTERMANN, H.

  DOI：——

  日期：——