(R)-N-benzyl-2-hydroxy-3-methylbutanamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-N-benzyl-2-hydroxy-3-methylbutanamide
• 英文别名: (R)-N-benzyl-2-hydroxy-3-methylbutyramide；N-benzyl-2-hydroxy-3-methylbutanamide；D-2-Hydroxy-isovaleriansaeure-benzylamid；(2R)-N-benzyl-2-hydroxy-3-methylbutanamide
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: AQSYWTVVFDMHSQ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  D-α-羟基异戊酸 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 (R)-N-benzyl-2-hydroxy-3-methylbutanamide
  参考文献：
  名称：

  Schroeder,E.; Luebke,K., Justus Liebigs Annalen der Chemie, 1962, vol. 655, p. 211 - 218

  摘要：

  DOI：

文献信息

• 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。
• Biocatalytic reduction of α-keto amides to (R)-α-hydroxy amides using Candida parapsilosis ATCC 7330
  作者：Selvaraj Stella、Anju Chadha

  DOI：10.1016/j.cattod.2012.03.081

  日期：2012.12

  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.
• Massive Parallel Catalyst Screening:  Toward Asymmetric MCRs
  作者：Ulrike Kusebauch、Barbara Beck、Kim Messer、Eberhardt Herdtweck、Alexander Dömling

  DOI：10.1021/ol035010u

  日期：2003.10.1

  [GRAPHIC]Hundreds of Lewis acid/ligand combinations have been screened for stereochemical induction in the Passerini multicomponent reaction. The combination of titan tetraisopropylate and (4S,5S)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyidioxolane was found to give enantiomeric excesses between 32% and 42% in several examples. The absolute stereo induction of one example was determined chemically and by means of X-ray crystallography. This comprises the first asymmetric Passerini reaction and the first example of a stereochernical induction in an isocyanide based multicomponent reaction by a chiral Lewis acid.