2-乙酰氨基-2-苯基乙酸甲酯 | 36061-00-4

• 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: 2-乙酰氨基-2-苯基乙酸甲酯
• 英文名称: methyl 2-acetamido-2-phenylacetate
• 英文别名: N-Ac-phenylglycine-OMe
• CAS: 36061-00-4
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: SAPRVTLHJXZROQ-UHFFFAOYSA-N

物化性质

• 熔点：
  115.2-117.3 °C
• 沸点：
  368.4±30.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  2-乙酰氨基-2-苯基乙酸甲酯 在 盐酸 、 水 作用下， 反应 18.0h， 以85%的产率得到2-氨基-2-苯基乙酸
  参考文献：
  名称：

  Synthesis of Arylglycines from CO₂through α-Amino Organomanganese Species

  摘要：

  In the presence of three readily available chemicals, Mn powder, BF3 center dot OEt2, and LiCl, N-acyl-N,O-acetals were successfully converted into the corresponding alpha-amino acids (arylglycine derivatives) under 1 atm of a CO2 atmosphere in high yields. The LiCl additive is necessary in order to increase the solubility and the nucleophilicity of an organomanganese intermediate. The products thus obtained were transformed into free alpha-amino acids in two steps.

  DOI：

  10.1021/ol500701n
• 作为产物：
  描述：

  苯甲酰甲酸甲酯 在 palladium on activated charcoal 吡啶 、 甲酸铵 作用下， 以 乙二醇 为溶剂， 反应 0.17h， 生成 2-乙酰氨基-2-苯基乙酸甲酯
  参考文献：
  名称：

  Microwave-Assisted Rapid and Simplified Hydrogenation^1,

  摘要：

  Catalytic transfer hydrogenation has been conducted under microwave irradiation in open vessels using high-boiling solvents such as ethylene glycol (bp 198 degrees C) as the microwave energy transfer agent. Reduction of double bonds and hydrogenolysis of several functional groups were carried out safely and rapidly (3-5 min) at about 110-130 degrees C with 10% Pd/C as an efficient catalyst and ammonium formate as the hydrogen donor. Diverse types of beta-lactam synthons were prepared by the reduction of ring substituents containing alkene and alkylidene groups or conjugated unsaturated esters, Cleavage of the beta-lactam ring by hydrogenolysis of the N-C-4 bond of 4-aryl-2-azetidinones was a facile reaction with 10% Pd/C as the catalyst; but no ring scission occurred when Raney nickel catalyst was employed. Dehalogenation of aromatic compounds was also successful with ammonium formate and Pd/C catalyst. Hydrogenolysis of phenylhydrazone of methyl benzoylformate gave the methyl ester of phenylglycine in excellent yield. The techniques described here for microwave assisted hydrogenation are safe, rapid, and efficient and are suitable for research investigation as well as for undergraduate and high school laboratory exercises.

  DOI：

  10.1021/jo981516s

文献信息

• A general and accurate nmr determination of the enantiomeric purity of α-aminoacids and α-aminoacid derivatives
  作者：Monique Calmes、Jacques Daunis、Robert Jacquier、Jean Verducci

  DOI：10.1016/s0040-4020(01)86812-5

  日期：——

  Derivatization of α-aminoacids, α-aminoesters and α-aminolactones as N-acetyl derivatives allow the accurate NMR determination of the enantiomeric purity. In these conditions the major coordination site with a chiral shift reagent will correspond to the NMR observation site. Experimental factors leading to the highest ΔΔδ values are ascertained. No straightforward correlation with absolute configurations

  作为N-乙酰基衍生物的α-氨基酸，α-氨基酯和α-氨基内酯的衍生化可以对对映体纯度进行准确的NMR测定。在这些条件下，具有手性移位试剂的主要配位点将对应于NMR观察位点。确定导致最高ΔΔδ值的实验因素。无法建立与绝对配置的直接关联。
• Acyl Transfer Catalysis with 1,2,4-Triazole Anion
  作者：Xing Yang、Vladimir B. Birman

  DOI：10.1021/ol900098q

  日期：2009.4.2

  1,2,4-Triazole anion has been identified as an active acyl transfer catalyst suitable for the aminolysis and transesterification of esters.

  1,2,4-三唑阴离子已被确定为一种活性酰基转移催化剂，适用于酯的氨解和酯交换。
• Enzymes in organic synthesis: use of subtilisin and a highly stable mutant derived from multiple site-specific mutations
  作者：Chi Huey Wong、S. T. Chen、William J. Hennen、Jeffrey A. Bibbs、Y. F. Wang、Jennifer L. C. Liu、Michael W. Pantoliano、Marc Whitlow、Philip N. Bryan

  DOI：10.1021/ja00159a006

  日期：1990.1

  wild-type enzyme to organic synthesis has been demonstrated in the regioselective acylation of nucleosides in anhydrous dimethylformamide (with 65-100% regioselectivity at the 5'-position), in the enantioselective hydrolysis of N-protected and unprotected common and uncommon amino acid esters inmore » water (with 85-98% enantioselectivity for the L-isomer), and in the synthesis of di- and oligopeptides

  发现通过六个位点特异性突变（Met50Phe、Gly169Ala、Asn76Asp、Gln206Cys、Tyr2l7Lys 和 Asn2l8Ser）衍生自枯草杆菌蛋白酶 BPN' 的枯草杆菌蛋白酶突变体（枯草杆菌蛋白酶 8350）在水溶液中比野生溶液中的稳定性高 100 倍在无水二甲基甲酰胺中比野生型稳定 50 倍。使用酯、硫酯和酰胺底物以及过渡态类似物抑制剂 Boc-Ala-Val-Phe-CFsub 3} 的动力学研究表明，野生型和突变型酶具有非常相似的特异性和催化作用特性。野生型酶的抑制常数 (Ki = 5.0 mu}M) 是突变酶 (Ki = 1.1 mu}M) 的约 5 倍，表明突变酶与反应过渡态的结合比野生型酶。该结果与观察到的相应酯和酰胺底物的速率常数一致；即，突变体的 ksub cat}/Ksub m} 值大于野生型酶的值。突变酶和野生型酶在有机合成中的应用已在无
• Organocatalytic Deuteration Induced by the Dynamic Covalent Interaction of Imidazolium Cations with Ketones
  作者：Konstantin I. Galkin、Evgeniy G. Gordeev、Valentine P. Ananikov

  DOI：10.1002/adsc.202001507

  日期：2021.3.2

  organocatalytic approach based on the dynamic covalent interaction of imidazolium cations with ketones. A reaction of N‐alkyl imidazolium salts with acetone‐d6 in the presence of oxygenated bases generates a dynamic organocatalytic system with a mixture of protonated carbene/ketone adducts acting as H/D exchange catalysts. The developed methodology of the pH‐dependent deuteration showed high selectivity of labeling

  在本文中，我们提出了一种基于咪唑鎓阳离子与酮的动态共价相互作用的新的有机催化方法。N-烷基咪唑鎓盐与丙酮d 6在含氧碱的存在下反应生成动态有机催化体系，质子化的卡宾/酮加合物作为H / D交换催化剂。已开发的pH依赖性氘代方法显示出较高的标记选择性和良好的手性官能团耐受性。在这里，我们报告了一种有效的无金属氘化的独特方法，该方法可以标记各种类型的α-酸性化合物而不会造成痕量金属污染。
• Iridium Porphyrin Catalyzed N–H Insertion Reactions: Scope and Mechanism
  作者：Bernie J. Anding、L. Keith Woo

  DOI：10.1021/om400098v

  日期：2013.5.13

  Ir(TTP)CH3 catalyzed N–H insertion reactions between ethyl diazoacetate (EDA) or methyl phenyldiazoacetate (MPDA) and a variety of aryl, aliphatic, primary, and secondary amines to generate substituted glycine esters with modest to high yields. Aniline substrates generally gave yields above 80%, with up to 105 catalyst turnovers, and without slow addition of the diazo reagent. Good yields were also achieved

  Ir（TTP）CH 3催化重氮乙酸乙酯（EDA）或苯基重氮乙酸甲酯（MPDA）与各种芳基，脂肪族，伯和仲胺之间的N–H插入反应，以中等至高收率生成取代的甘氨酸酯。苯胺底物的收率通常超过80％，催化剂的转化率高达10 5，并且没有缓慢添加重氮试剂。尽管在某些情况下需要更高的催化剂负载量和胺的缓慢添加，但脂肪族胺也能获得良好的收率。伯胺与EDA反应生成单，双-插入产品，其中任一个的可在高产率下的化学计量比和反应温度的适当选择有选择地来制备。值得注意的是，混合三取代胺RN（CH通过在伯胺中插入1当量的EDA和1当量的MPDA生成2 CO 2 Et）（CHPhCO 2 Me）。使用底物竞争研究，捕获实验和多种光谱技术检查了N–H插入机制。使用具有EDA或MPDA的成对胺进行的底物竞争研究显示HammeTT相关性分别具有ρ= 0.15和ρ + = -0.56的斜率以及k H / k D的动力学同位素比=