N-(4-甲基苯甲酰)-甘氨酸乙酯 | 122081-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-甲基苯甲酰)-甘氨酸乙酯
• 英文名称: N-(4-methyl)benzoyl glycine ethylester
• 英文别名: ethyl 2-(4-methylbenzamido)acetate；N-p-toluoyl-glycine ethyl ester；N-p-Toluoyl-glycin-aethylester；Ethyl 2-[(4-methylbenzoyl)amino]acetate
• CAS: 122081-29-2
• 化学式: C₁₂H₁₅NO₃
• mdl: MFCD00793748
• 分子量: 221.256
• InChiKey: PQHQYXFXTGCTNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 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

反应信息

• 作为反应物：
  描述：

  N-(4-甲基苯甲酰)-甘氨酸乙酯 以88%的产率得到
  参考文献：
  名称：

  Singh Kumar K., Singh Radhey M., Indian. J. Chem. B, 33 (1994) N 3, S 232-235

  摘要：

  DOI：
• 作为产物：
  描述：

  HONC(CH3)C(CH3)NNHC(O)C6H4CH3-p 在 lead(IV) acetate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 0.52h， 生成 N-(4-甲基苯甲酰)-甘氨酸乙酯
  参考文献：
  名称：

  1-芳酰氧基-4,5-二甲基-1,2,3-三唑的合成，结构和酰化性能

  摘要：

  联乙酰的α-羟基亚氨基芳酰基hydr的四乙酸铅氧化（1）得到1-芳酰氧基-4,5-二甲基-1,2,3-三唑（2），其结构通过X射线分析证实。讨论了该反应的机理。产物（2）是在温和条件下对氨基官能团有效的芳香化剂。

  DOI：

  10.1039/p19890000619

文献信息

• The α-Effect in Hydrazinolysis of 4-Chloro-2-Nitrophenyl X-Substituted-Benzoates: Effect of Substituent X on Reaction Mechanism and the α-Effect
  作者：Min-Young Kim、Tae-Eun Kim、Jieun Lee、Ik-Hwan Um

  DOI：10.5012/bkcs.2014.35.8.2271

  日期：2014.8.20

  Second-order rate constants ($k_N$) have been measured spectrophotometrically for the reaction of 4-chloro-2-nitrophenyl X-substituted-benzoates (6a-6h) with a series of primary amines including hydrazine in 80 mol % $H_2O$/20 mol % DMSO at $25.0^\circ}C$. The Br$\o}$nsted-type plot for the reaction of 4-chloro-2-nitrophenyl benzoate (6d) is linear with $\beta}_nuc}$ = 0.74 when hydrazine is excluded from the correlation. Such a linear Br$\o}$nsted-type plot is typical for reactions reported previously to proceed through a stepwise mechanism in which expulsion of the leaving group occurs in the rate-determining step (RDS). The Hammett plots for the reactions of 6a-6h with hydrazine and glycylglycine are nonlinear. In contrast, the Yukawa-Tsuno plots exhibit excellent linear correlations with $\rho}_X$ = 1.29-1.45 and r = 0.53-0.56, indicating that the nonlinear Hammett plots are not due to a change in RDS but are caused by resonance stabilization of the substrates possessing an electron-donating group (EDG). Hydrazine is ca. 47-93 times more reactive than similarly basic glycylglycine toward 6a-6h (e.g., the $\alpha}$-effect). The $\alpha}$-effect increases as the substituent X in the benzoyl moiety becomes a stronger electron-withdrawing group (EWG), indicating that destabilization of the ground state (GS) of hydrazine through the repulsion between the nonbonding electron pairs on the two N atoms is not solely responsible for the substituent-dependent $\alpha}$-effect. Stabilization of transition state (TS) through five-membered cyclic TSs, which would increase the electrophilicity of the reaction center or the nucleofugality of the leaving group, contributes to the $\alpha}$-effect observed in this study.

  二次速率常数（$k_N$）已通过分光光度法测定，用于4-氯-2-硝基苯基X取代苯甲酸酯（6a-6h）与一系列伯胺（包括80摩尔% $H_2O$/20摩尔% DMSO中的25.0°C下的联氨）的反应。当联氨被排除在相关性之外时，4-氯-2-硝基苯基苯甲酸酯（6d）反应的Br$\o}$nsted型图是线性的，$\beta}_nuc}$ = 0.74。这种线性Br$\o}$nsted型图是典型的反应，先前报道这些反应通过逐步机制进行，其中离去基团的排出发生在速率决定步骤（RDS）中。6a-6h与联氨和甘氨酰甘氨酸反应的Hammett图是非线性的。相比之下，Yukawa-Tsuno图显示出极佳的线性相关性，$\rho}_X$ = 1.29-1.45，r = 0.53-0.56，表明非线性Hammett图并非由于RDS的变化，而是由于具有供电子基团（EDG）的底物的共振稳定化所导致。联氨对6a-6h的反应性大约是同样碱性的甘氨酰甘氨酸的47-93倍（例如，$\alpha}$效应）。随着苯甲酰基中取代基X成为更强的吸电子基团（EWG），$\alpha}$效应增加，表明通过两个N原子上的非键电子对之间的排斥来破坏联氨的基态（GS）并不是唯一导致取代基依赖的$\alpha}$效应的原因。通过五元环过渡态（TS）的稳定化，这将增加反应中心的亲电性或离去基团的离核性，有助于在本研究中观察到的$\alpha}$效应。
• Microwave-Assisted Ruthenium-Catalysed <i>ortho</i> -C−H Functionalization of <i>N</i> -Benzoyl <i>α</i> -Amino Ester Derivatives
  作者：Nandini Sharma、Vijay Bahadur、Upendra K. Sharma、Debasmita Saha、Zhenghua Li、Yogesh Kumar、Jona Colaers、Brajendra K Singh、Erik V. Van der Eycken

  DOI：10.1002/adsc.201800458

  日期：2018.8.17

  A microwave‐assisted highly efficient intermolecular C−H functionalization sequence has been developed to access substituted isoquinolones using α‐amino acid esters as a directing group. This methodology enables a wide range of N‐benzoyl α‐amino ester derivatives to react via a Ru‐catalysed C−H bond activation sequence, to form isoquinolones with moderate to excellent yields. As an additional advantage

  微波辅助高效分子间C-H官能化序列已经发展到使用访问取代的异喹诺酮化合物α -氨基乙酸酯定向基团。这种方法可以使大量的N-苯甲酰基α-氨基酯衍生物通过Ru催化的CH键激活序列反应，以中等到极好的收率形成异喹诺酮类化合物。作为一个额外的优势，我们的策略被证明具有广泛的适用性，并且还使烯烃的反应能够提供链烯基化的苯甲酰胺的途径。该方法还扩展到异喹啉生物碱衍生物的合成，即。氧鸟嘌呤和二肽。所开发的方案既简单又便宜，避免了繁琐的后处理程序，并在MW辐射下有效地工作。
• Therapy for urolithiasis with hydroxamic acids. I. Synthesis of new N-(aroyl)glycinohydroxamic acid derivatives and related compounds.
  作者：KEIICHI MUNAKATA、SATORU TANAKA、SHOJI TOYOSHIMA

  DOI：10.1248/cpb.28.2045

  日期：——

  With the aim of finding a therapeutic agent for urolithiasis, forty-three new N-(aroyl)-glycinohydroxamic acid derivatives and related compounds were synthesized and examined for urease inhibitory activity. Their urinary excretion in rats was also determined.

  为了寻找针对尿路结石的治疗药物，我们合成了四十三种新的N-(芳酰基)-甘氨酸羟肟酸衍生物及相关化合物，并检测了它们的脲酶抑制活性。同时，我们还确定了这些化合物在大鼠体内的尿液排泄情况。
• Copper-Catalyzed Aerobic Oxidative [2 + 3] Cyclization/Aromatization Cascade Reaction: Atom-Economical Access to Tetrasubstituted 4,5-Biscarbonyl Imidazoles
  作者：Jialin Xie、Yuanqiong Huang、Hongjian Song、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.7b02767

  日期：2017.11.17

  An atom-economical method for accessing tetrasubstituted 4,5-biscarbonylimidazoles by reaction between glycine derivatives and 5-alkoxyoxazoles is reported. The method, which involves a copper-catalyzed aerobic oxidative [2 + 3] cyclization/aromatization cascade process, starts from readily available and inexpensive materials, uses molecular oxygen as a co-oxidant, and has a broad substrate scope.

  报道了通过甘氨酸衍生物和5-烷氧基恶唑之间的反应获得四取代的4，5-双羰基咪唑的原子经济方法。该方法涉及铜催化的好氧氧化[2 + 3]环化/芳香化反应级联过程，从容易获得且廉价的材料开始，使用分子氧作为助氧化剂，具有广泛的底物范围。
• Highly Efficient Oxidative Amidation of Aldehydes with Amine Hydrochloride Salts
  作者：Woo-Jin Yoo、Chao-Jun Li

  DOI：10.1021/ja064315b

  日期：2006.10.1

  A mild and efficient copper-catalyzed oxidative amidation of aldehydes was developed using amine HCl salts and tert-butyl hydroperoxide as an oxidant.

  使用胺盐酸盐和叔丁基氢过氧化物作为氧化剂开发了一种温和而有效的铜催化的醛氧化酰胺化。