N-acetylglutamic acid ethyl ester | 1907-89-7

• 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
• 英文名称: N-acetylglutamic acid ethyl ester
• 英文别名: diethyl acetylglutamate；N-Acetyl-glutaminsaeure-diaethylester；N-Acetyl-DL-glutaminsaeure-diaethylester；N-acetyl-glutamic acid diethyl ester；diethyl N-acetyl-glutamate；Glutamic acid, N-acetyl-, diethyl ester, L-；diethyl 2-acetamidopentanedioate
• CAS: 1907-89-7
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: FBAOQDIATMHNAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-acetylglutamic acid ethyl ester 在 sodium hydroxide 、 sodium chloride 、 α-chymotrypsin 作用下， 生成 (S)-N-acetyl glutamic acid ο-ethyl ester
  参考文献：
  名称：

  Kinetics of Hydrolysis of Dicarboxylic Esters and Their α-Acetamido Derivatives by α-Chymotrypsin

  摘要：

  DOI：

  10.1021/ja01076a053
• 作为产物：
  描述：

  Methyl-2-amino-4-aethoxycarbonylbutyrat 在 吡啶 、 sodium methylate 作用下， 生成 N-acetylglutamic acid ethyl ester
  参考文献：
  名称：

  面包酵母的对映体选择性水解-II：正乙酰基氨基酸的酯1

  摘要：

  DN-乙酰基氨基酸酯是通过使用发酵酵母通过其外消旋物的对映体选择性水解而获得的。有证据表明蛋白酶是所涉及的酶。

  DOI：

  10.1016/s0040-4020(01)90011-0

文献信息

• Metal-Free Decarboxylative Hetero-Diels–Alder Synthesis of 3-Hydroxypyridines: A Rapid Access to <i>N</i>-Fused Bicyclic Hydroxypiperidine Scaffolds
  作者：Laurie-Anne Jouanno、Vincent Di Mascio、Vincent Tognetti、Laurent Joubert、Cyrille Sabot、Pierre-Yves Renard

  DOI：10.1021/jo402729a

  日期：2014.2.7

  A complete experimental and theoretical study of the thermally controlled metal-free decarboxylative hetero-Diels–Alder (HDA) reaction of 5-alkoxyoxazoles with acrylic acid is reported. This strategy offers a new entry to valuable 2,6-difunctionalized 3-hydroxypyridines from readily available 2- and 4-disubstituted 5-alkoxyoxazoles. The reaction conditions proved compatible with, among others, ketone

  报道了5-烷氧基恶唑与丙烯酸热控制的无金属脱羧杂狄尔斯-阿尔德（HDA）反应的完整实验和理论研究。该策略为易于获得的2-和4-二取代的5-烷氧基恶唑提供了有价值的2,6-二官能化的3-羟基吡啶的新入口。证明该反应条件尤其与酮，酰胺，酯，醚和腈基相容。该方案具有广泛的官能团耐受性，可通过吡啶脱芳构化策略快速而通用地获得羟基吲哚并咪唑和羟基喹oli嗪衍生物。
• Enantioselective hydrolysis by baker's yeast
  作者：B.I. Glänzer、K. Faber、H. Griengl

  DOI：10.1016/s0040-4039(00)94256-4

  日期：——

  Optically active N-acetylamino acid esters were obtained by enantioselective hydrolysis of their racemates using fermenting baker's yeast.

  光学活性的N-乙酰基氨基酸酯是通过使用发酵酵母进行对映体的对映体水解而获得的。
• ANTI-ODOR COMPOSITIONS AND THERAPEUTIC USE
  申请人：Yu J. Ruey

  公开号：US20060251597A1

  公开（公告）日：2006-11-09

  This application discloses a composition comprising a malodor compound and an anti-odor ingredient effective for reducing the presence or production of malodor. The composition may be topically applied to a subject and is useful for cosmetic conditions, pharmaceutical indications, or other objectives.

  本申请公开了一种包含恶臭化合物和抑臭成分的组合物，用于减少恶臭的存在或产生。该组合物可以局部应用于一个对象，并且适用于化妆条件、药用指示或其他目的。
• Site-Specific Functionalization of 1,3-Dioxolane with Imines: A Radical Chain Approach to Masked α-Amino Aldehydes
  作者：Haipeng Zeng、Sen Yang、Haotian Li、Dengfu Lu、Yuefa Gong、Jin-Tao Zhu

  DOI：10.1021/acs.joc.8b00715

  日期：2018.5.4

  A thiol-promoted site-specific addition of 1,3-dioxolane to imines through a radical chain process is described. This process represents a metal-free and redox-neutral way to convert inexpensive materials to a broad range of protected α-amino aldehydes in good to excellent yields using only a catalytic amount of radical precursor. Control experiments revealed that both the thiol and a small amount

  描述了通过自由基链过程向亚胺的硫醇促进的位点特异性加成的1，3-二氧戊环。该方法代表了一种无金属和氧化还原中性的方法，该方法仅使用催化量的自由基前体即可将廉价的材料以良好或优异的收率转化为多种受保护的α-氨基醛。对照实验表明，硫醇和空气中的少量氧气对于该反应的成功是必不可少的。
• New processes for the production of di-alkyl esters and optically active mono-alkyl esters of 3-aminoglutaric acid
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0050799A1

  公开（公告）日：1982-05-05

  A new process is provided for the production of a di-alkyl 3-aminoglutarate which are found useful as intermediates for the synthesis of β-lactam antibiotics of carbapenem type such as thienamycin. The new process comprises reacting an ammonium salt or ammonia with a di-alkyl ester of 3- ketoglutaric acid to form unsaturated amine compounds and reducing the latter with an alkali metal cyanoborohydride. The N-protected derivative of di-alkyl 3-aminoglutarate prepared may be converted into the optically active p-(S)-mono-alkyl half ester by treatment with esterase to hydrolyze only one of the esters (pro-R ester), followed by conventional N-deprotection. Further, di-alkyl 3-aminoglutarate itself may immediately be converted into the optically active β-(R)-mono-alkyl half ester of 3-aminoglutaric acid by treatment with esterase to hydrolyze preferentially one ester-forming alkyl group (pro-S ester).

  本发明提供了一种生产 3-酮戊二酸二烷基酯的新工艺，这种二烷基酯可用作合成碳青霉烯类 β-内酰胺抗生素（如噻那霉素）的中间体。新工艺包括铵盐或氨与 3- 酮戊二酸的二烷基酯反应生成不饱和胺化合物，并用碱金属氰硼氢化物还原后者。制备的 3-氨基戊二酸二烷基酯的 N 保护衍生物可以通过酯酶处理，仅水解其中一个酯（原-R 酯），然后进行常规的 N-脱保护，转化为具有光学活性的对-(S)-单烷基半酯。此外，3-氨基戊二酸二烷基酯本身也可以立即转化为具有光学活性的 3-氨基戊二酸 β-(R)-单烷基半酯，方法是用酯酶优先水解一个成酯烷基（pro-S 酯）。