N-benzyl-2-hydroxy-2-(4'-chlorophenyl)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-2-hydroxy-2-(4'-chlorophenyl)acetamide
• 英文别名: N-benzyl-2-(4-chlorophenyl)-2-hydroxyacetamide
• 化学式: C₁₅H₁₄ClNO₂
• 分子量: 275.735
• InChiKey: XCIPCQBNKIFHJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-hydroxy-2-(4'-chlorophenyl)acetamide 在 2,2,6,6-四甲基哌啶氧化物 、 calcium methylate 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到N-benzyl-2-(4-chlorophenyl)-2-oxoacetamide
  参考文献：
  名称：

  TEMPO 催化氧化的简化程序：使用 TEMPO 和次氯酸钙选择性氧化醇、α-羟基酯和酰胺

  摘要：

  摘要 在温和的反应条件下，使用 2,2,6,6-四甲基哌啶将多种伯多官能团醇、α-羟基酰胺和 α-羟基酯氧化成相应的醛、酮、α-酮酰胺和 α-酮酯。 -1-氧基作为催化剂，次氯酸钙作为氧化剂[TEMPO-Ca(OCl)2]。这种简化的方法不需要任何过渡金属、酸或碱，并且展示了结构多样的醇的受控和选择性氧化，在室温下提供中等至极好的收率。图形概要

  DOI：

  10.1080/00397911.2011.584650
• 作为产物：
  描述：

  对氯扁桃酸 、 苄胺 生成 N-benzyl-2-hydroxy-2-(4'-chlorophenyl)acetamide
  参考文献：
  名称：

  Biocatalytic reduction of α-keto amides to (R)-α-hydroxy amides using Candida parapsilosis ATCC 7330

  摘要：

  Biocatalytic reduction of primary and secondary alpha-keto amides was accomplished using whole cells of Candida parapsilosis ATCC 7330. The primary (R)-alpha-hydroxy amides were obtained in good enantiomeric excess (up to 94%) and conversion (88-99%) as compared to the secondary (R)-alpha-hydroxy amides. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cattod.2012.03.081

文献信息

• [EN] REAGENTS AND METHODS FOR ESTERIFICATION<br/>[FR] RÉACTIFS ET PROCÉDÉS D'ESTÉRIFICATION
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2016164622A1

  公开（公告）日：2016-10-13

  Methods and reagents for esterification of biological molecules including proteins, polypeptides and peptides. Diazo compounds of formula (I): where R is hydrogen, an alkyl, an alkenyl or an alkynyl, RA represents 1-5 substituents on the indicated phenyl ring and RM is an organic group, which includes a label, a cell penetrating group, a cell targeting group, or a reactive group or latent reactive group for reaction to bond to a label, a cell penetrating group, or a cell targeting group, among other organic groups are useful for esterification of biological molecules. Also provided are diazo compounds which are bifunctional and trifunctional coupling reagents as well as reagents for the synthesis of compounds of formula (I).

  用于酯化生物分子，包括蛋白质、多肽和肽的方法和试剂。式(I)的重氮化合物：其中R为氢、烷基、烯基或炔基，RA代表指定苯环上的1-5个取代基，RM为有机基团，其中包括标记、穿透细胞基团、靶向细胞基团、或用于与标记、穿透细胞基团或靶向细胞基团结合的反应基团或潜在反应基团，等其他有机基团，对于生物分子的酯化是有用的。还提供了具有双功能和三功能偶联试剂以及合成式(I)化合物的试剂的重氮化合物。
• Asymmetric Aerobic Oxidation of α-Hydroxy Acid Derivatives Catalyzed by Reusable, Polystyrene-Supported Chiral N-Salicylidene Oxidovanadium tert-Leucinates
  作者：Santosh B. Salunke、N.Seshu Babu、Chien-Tien Chen

  DOI：10.1002/adsc.201100062

  日期：2011.5

  The direct immobilization of two different C‐5‐propargyl ether‐modified, chiral N‐salicylidene vanadyl(V) tert‐leucinates onto 4‐azidomethyl‐substituted polystyrene by click chemistry was examined. Among the eight different solvents investigated, the resulting polystyrene‐supported catalysts promote the asymmetric, aerobic oxidation of α‐hydroxy (thio)esters and amides with enantioselectivities of

  通过点击化学方法研究了将两种不同的C-5-炔丙基醚改性的手性N-水杨基亚烷基钒（V）叔亮氨酸酯直接固定在4-叠氮基甲基取代的聚苯乙烯上的方法。在所研究的八种不同溶剂中，所得的聚苯乙烯负载催化剂促进了α-羟基（硫代）酯和酰胺的不对称，好氧氧化，其在氯仿中的对映选择性高达99％ee（选择性高达41）。这些聚苯乙烯负载的催化剂可以很容易地通过过滤回收，并至少连续四次重复使用，而不会损失反应性和对映选择性。
• Reagents and methods for esterification
  申请人：Wisconsin Alumni Research Foundation

  公开号：US10428323B2

  公开（公告）日：2019-10-01

  Methods and reagents for esterification of biological molecules including proteins, polypeptides and peptides. Diazo compounds of formula I: where R is hydrogen, an alkyl, an alkenyl or an alkynyl, RA represents 1-5 substituents on the indicated phenyl ring and RM is an organic group, which includes a label, a cell penetrating group, a cell targeting group, or a reactive group or latent reactive group for reaction to bond to a label, a cell penetrating group, or a cell targeting group, among other organic groups are useful for esterification of biological molecules. Also provided are diazo compounds which are bifunctional and trifunctional coupling reagents as well as reagents for the synthesis of compounds of formula I.

  生物分子（包括蛋白质、多肽和肽类）酯化的方法和试剂。式 I 的重氮化合物： 其中 R 是氢、烷基、烯基或炔基，RA 代表所示苯基环上的 1-5 个取代基，RM 是有机基团，其中包括标签、细胞渗透基团、细胞靶向基团或反应基团或潜伏反应基团，用于与标签、细胞渗透基团或细胞靶向基团等有机基团反应结合，可用于生物分子的酯化。此外，还提供了双官能和三官能偶联试剂的重氮化合物以及用于合成式 I 化合物的试剂。
• Optimized Diazo Scaffold for Protein Esterification
  作者：Kalie A. Mix、Ronald T. Raines

  DOI：10.1021/acs.orglett.5b00840

  日期：2015.5.15

  The O-alkylation of carboxylic acids with diazo compounds provides a means to esterify carboxylic acids in aqueous solution. A Hammett analysis of the reactivity of diazo compounds derived from phenylglycinamide revealed that the (p-methylphenyl)glycinamide scaffold has an especially high reaction rate and ester/alcohol product ratio and esterifies protein carboxyl groups more efficiently than any known reagent.
• Asymmetric Aerobic Oxidation of α-Hydroxy Acid Derivatives by <i>C</i>₄-Symmetric, Vanadate-Centered, Tetrakisvanadyl(V) Clusters Derived from <i>N</i>-Salicylidene-α-aminocarboxylates
  作者：Chien-Tien Chen、Sampada Bettigeri、Shiue-Shien Weng、Vijay D. Pawar、Ya-Hui Lin、Cheng-Yuan Liu、Way-Zen Lee

  DOI：10.1021/jo070575f

  日期：2007.10.1

  A series of chiral vanadyl(V) methoxides bearing 3-t-butyl-5-substituted N-salicylene-L-valinate and L-t-leucinate as chiral auxiliaries has been prepared. In all cases except the 3,5-di-t-butyl analogue, they exist as monomers both in solution and in the single crystal state. In the case of the 3,5-di-t-butyl analogue, the architectural nature of the vanadyl(V) complex highly depends on the base used during the complex formation event. A pentanuclear C-4-symmetric complex was formed when potassium salts were employed instead of the corresponding sodium salts. A central vanadate(V) unit serves to grip four identical chiral monomeric vanadyl(V) units together, by which a potassium ion sits on top of the four flanking units through carbonyl coordinations and serves to hold the whole cluster by cooperation with the central vanadate(V) unit. In comparison with the corresponding monomeric vanadyl(V) methoxide complex, the cluster complex was utilized to facilitate the asymmetric aerobic oxidations of various racemic alpha-hydroxyesters, -amides, and -thioesters with excellent selectivity factors (k(rel) 40 to >500).