N-benzyl-2-hydroxy-2-(thiophen-2-yl)acetamide | 143217-43-0

• 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-(thiophen-2-yl)acetamide
• 英文别名: N-benzyl-2-hydroxy-2-thiophen-2-ylacetamide
• CAS: 143217-43-0
• 化学式: C₁₃H₁₃NO₂S
• 分子量: 247.318
• InChiKey: UHSOFRPWDLNLBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  77.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-hydroxy-2-(thiophen-2-yl)acetamide 在 氧气 作用下， 以 氯仿 为溶剂， 反应 22.0h， 以35%的产率得到(S)-N-benzyl-2-hydroxy-2-thiophen-2-yl-acetamide
  参考文献：
  名称：

  可重复使用的聚苯乙烯负载的手性N-水杨基氧杂钒叔亮氨酸酯催化的α-羟基衍生物的不对称好氧氧化

  摘要：

  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。

  DOI：

  10.1002/adsc.201100062
• 作为产物：
  描述：

  2-噻吩乙酰氯 在 三乙胺 、 乙腈 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 N-benzyl-2-hydroxy-2-(thiophen-2-yl)acetamide
  参考文献：
  名称：

  Base-promoted reaction of O-sulfonylated hydroxamic acids with nucleophiles. A new method for the synthesis of .alpha.-substituted amides

  摘要：

  Treatment of a series of hydroxamic acids 2 with mesyl chloride in the presence of 2 equiv of triethylamine at 0-degrees-C gives 2-chloroamides 3 in good yields. Use of a single equivalent of triethylamine gives the (N-mesyl-oxy)amides 1, which are versatile synthetic intermediates as they can be readily converted to 2-bromoamides 4 with lithium bromide and triethylamine and to 2-hydroxyamides 5 with triethylamine in aqueous acetonitrile.

  DOI：

  10.1021/jo00047a024

文献信息

• 催化前手性α-酮酰胺合成手性α-羟基酰胺的方法
  申请人：凯特立斯（深圳）科技有限公司

  公开号：CN107417562A

  公开（公告）日：2017-12-01

  本发明提供了一种全新制备手性α‑羟基酰胺的方法，通过使用新型的三齿氮膦配体对具有前手性的α‑酮酰胺进行不对称氢化反应制备一系列的手性α‑羟基酰胺化合物，方法包括：在氢气氛围下，在催化剂的存在下，加入前手性α‑酮酰胺和碱进行不对称氢化反应，得到手性α‑羟基酰胺；所述催化剂是由金属铱盐与手性配体络合得到。所述方法所使用的配体容易合成，反应具有高对映选择性、高收率、高转化数的特点，绝大多数底物在催化剂用量万分之一的情况下取得99％以上的转化率和97％‑99％以上的ee值，最高转化数达到100000，具有极高的工业化价值。
• 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).
• An efficient boric acid-mediated preparation of α-hydroxyamides
  作者：J. Sravan Kumar、Subash C. Jonnalagadda、Venkatram R. Mereddy

  DOI：10.1016/j.tetlet.2009.12.008

  日期：2010.2

  An efficient methodology for the preparation of alpha-hydroxyamides via boric acid-mediated addition of isonitriles onto aldehydes has been developed. The reaction of isonitriles with alpha-boronobenzaldehyde takes place under intramolecular catalysis conditions to provide functionalized benzoxaboroles. (c) 2009 Elsevier Ltd. All rights reserved.
• Base-promoted reaction of O-sulfonylated hydroxamic acids with nucleophiles. A new method for the synthesis of .alpha.-substituted amides
  作者：Robert V. Hoffman、Naresh K. Nayyar、Wenting Chen

  DOI：10.1021/jo00047a024

  日期：1992.10

  Treatment of a series of hydroxamic acids 2 with mesyl chloride in the presence of 2 equiv of triethylamine at 0-degrees-C gives 2-chloroamides 3 in good yields. Use of a single equivalent of triethylamine gives the (N-mesyl-oxy)amides 1, which are versatile synthetic intermediates as they can be readily converted to 2-bromoamides 4 with lithium bromide and triethylamine and to 2-hydroxyamides 5 with triethylamine in aqueous acetonitrile.
• 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。