(R)-2-methyl-2-hydroxypentanoic acid | 135362-80-0

• 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)-2-methyl-2-hydroxypentanoic acid
• 英文别名: (2R)-2-hydroxy-2-methylpentanoic acid
• CAS: 135362-80-0
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: BIEZUWIUHAKFHZ-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-methyl-2-hydroxypentanoic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 甲苯 为溶剂， 生成 (R)-2-methyl-2-hydroxypentanoic acid methyl ester
  参考文献：
  名称：

  Screening for New Hydroxynitrilases from Plants

  摘要：

  我们建立了一种简单的高效液相色谱法来测定由苯甲醛和氰化物合成的手性扁桃腈的活性和立体化学性质，并将其用于筛选植物来源的羟腈裂解酶（HNL）活性。该方法共检测了 74 个科 163 种植物的 (R)- 和 (S)-HNL 活性。我们发现，百里香叶片的匀浆显示出（S）-HNL 活性，而西番莲的叶片和种子以及枇杷、柴胡、山梨、梅和柿的种子显示出（R）-HNL 活性。从西番莲和枇杷中部分纯化的（R）-HNLs 不仅对苯甲醛有作用，而且对脂肪族酮也有作用。利用西番莲叶片匀浆由 2-戊酮合成的(R)-甲基丙酮氰醇的对映体过量率为 87.0%，利用枇杷叶种子匀浆合成的(R)-扁桃腈的对映体过量率为 85.0%。

  DOI：

  10.1271/bbb.69.2349
• 作为产物：
  描述：

  (2R)-2-hydroxy-N,2-dimethylpentanamide 在 硫酸 作用下， 反应 30.0h， 以55%的产率得到(R)-2-methyl-2-hydroxypentanoic acid
  参考文献：
  名称：

  Asymmetric Allylation and Reduction on an Ephedrine-Derived Template:  Stereoselective Synthesis of α-Hydroxy Acids and Derivatives

  摘要：

  DOI：

  10.1021/jo9722820

文献信息

• METHOD FOR SYNTHESIS OF HALOPYRIDYL-ACYCLOPENTANE DERIVATIVE AND INTERMEDIATE THEREOF
  申请人：——

  公开号：US20020010339A1

  公开（公告）日：2002-01-24

  The present invention relates to a method for synthesis of an optically active halopyridyl-azacyclo-pentane derivative and the intermediate thereof which comprises preparing an optically active allene-1,3-dicarboxylic acid ester derivative from an optically active acetonedicarboxylic acid ester derivative and then proceeding through a 7-azabicyclo[2.2.1]heptane derivative to obtain the objective product.

  本发明涉及一种合成光学活性卤代吡啶-氮杂环戊烷衍生物及其中间体的方法，包括从光学活性丙酮二羧酸酯衍生物制备光学活性联二烯-1,3-二羧酸酯衍生物，然后通过7-氮杂双环[2.2.1]庚烷衍生物进行反应，以获得目标产物。
• Enzyme-catalyzed synthesis or (R)-ketone-cyanohydrins and their hydrolysis to (R)-α-hydroxy-α-methyl-carboxylic acids
  作者：Franz Effenberger、Brigitte Hörsch、Franz Weingart、Thomas Ziegler、Stefan Kühner

  DOI：10.1016/s0040-4039(00)78796-x

  日期：1991.6

  (R)-Ketone-cyanohydrins (R)-2 are obtained with high enantioselectivity from aliphatic ketones 1 and HCN in organic solvents using (R)-oxynitrilase (EC 4.1.2.10) as catalyst. Acid catalyzed hydrolysis of the cyanohydrins (R)-2 affords the corresponding (R)-alpha-hydroxy-alpha-methyl-carboxylic acids (R)-3 without measurable racemization.
• A General Strategy to Enantiomerically Pure Aliphatic and Olefinic Ketone Cyanohydrins by Stereoselective Alkylation of Umpoled Aldehyde Derivatives
  作者：Christian N. Kirsten、Michael Herm、Thomas H. Schrader

  DOI：10.1021/jo970854a

  日期：1997.10.1

  We present the first general synthesis of optically pure (R)- and (S)-ketone cyanohydrins with olefinic and aliphatic substituents. Consecutive condensations of POCl3 with pseudoephedrine (1) and racemic crotonaldehyde cyanohydrin (3, R = 1-propenyl) lead to the respective cyanohydrin phosphate 4c. Deprotonation, followed by highly stereoselective alkylation and a single chromatographic purification step, afford diastereomerically pure ketone cyanohydrin phosphates 5a-e. From these, enantiomerically pure tertiary cyanohydrins 6a-e can be obtained by mild Lewis acid-assisted hydrolysis. Pseudoephedrine is simultaneously recovered without loss of optical purity. The unsaturated alkylation products 5a-d are readily hydrogenated with diimide to aliphatic cyanohydrin phosphates 5f-i, which can be cleaved to furnish the free optically pure cyanohydrins 6f-i. Thus a broad variety of both saturated and unsaturated ketone cyanohydrins with R > Et becomes accessible in optically pure form for the first time. The free cyanohydrins are easily converted to optically pure alpha-branched alpha-hydroxy acids.
• Process for synthesizing cyclic depsipeptides
  申请人：TAKARA SHUZO CO. LTD.

  公开号：EP0581429B1

  公开（公告）日：1997-09-03
• EP0581429A2
  申请人：——

  公开号：EP0581429A2

  公开（公告）日：1994-02-02