(R)-methyl 2-hydroxy-4-methylpentanoate | 112529-90-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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)-methyl 2-hydroxy-4-methylpentanoate
• 英文别名: methyl L-2-hydroxy-4-methylpentanoate；methyl (2R)-2-hydroxy-4-methylpentanoate
• CAS: 112529-90-5
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: JOSNYUDSMPILKL-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 储存条件：
  密封于干燥常温环境

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-hydroxy-4-methylpentanoate 在 2,6-二甲基吡啶 、 sodium hydroxide 、 三甲基溴硅烷 、 1,8-双二甲氨基萘 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 164.0h， 生成 N--O-methyl-(S)-tyrosine N-methyl amide
  参考文献：
  名称：

  Synthesis of novel N-phosphonoalkyl dipeptide inhibitors of human collagenase

  摘要：

  The synthesis of a series of N-phosphonoalkyl dipeptides 6 is described. Syntheses were devised that allowed the preparation of single diastereoisomers and the assignment of stereochemistry. The compounds were evaluated in vitro for their ability to inhibit the degradation of radiolabeled collagen by purified human lung fibroblast collagenase. Several of the compounds were potent collagenase inhibitors and were at least l0-fold more potent than their corresponding N-carboxyalkyl analogues. Activity was lost when the phosphonic acid group P(O)(OH)(2) was replaced by the phosphinic acid groups P(O)(H)(OH) and P(O)(Me)(OH). At the P-1 position, (R)- or (S)-allkyl groups, especially ethyl and methyl (e.g., 12a,b, 52a,b, and 53a,b), or an (R)-phenethyl moiety (55a) conferred high potency (IC50 values in the range 0.23-0.47 mu M). (S)-Stereochemistry was preferred for the P-1(') isobutyl side chain. Structure-activity relationships were also investigated at the P-2(') site, and interestingly, compounds with basic side chains such as the guanidine 57a, were equipotent with more lipophilic compounds, such as 52a. As with other series of collagenase inhibitors, potency was enhanced by introducing bicyclic aromatic P-2(') substituents. The most potent phosphonic acid of the series was the bicyclic aromatic P-2(') tryptophan analogue 59a (IC50 0.05 mu M).

  DOI：

  10.1021/jm00027a020
• 作为产物：
  描述：

  D-亮氨酸 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 3.0h， 生成 (R)-methyl 2-hydroxy-4-methylpentanoate
  参考文献：
  名称：

  通过有机催化共轭添加α-氰基乙酸酯到甲基丙烯酸甲酯上的全碳叔/季不相邻立体中心的不对称组装

  摘要：

  基于布朗斯台德碱催化的迈克尔加成/α-质子化序列，涉及α-氰基乙酸酯和2,4-二甲基-4-基羟基戊烯-3-一作为新的甲基丙烯酸酯等同物。

  DOI：

  10.1002/chem.201603082
• 作为试剂：
  描述：

  1-acetoxy-2-benzylcyclohexene 在 甲基锂 、 (R)-methyl 2-hydroxy-4-methylpentanoate 作用下， 生成 (S)-2-benzylcyclohexanone 、 (R)-2-benzylcyclohexanone
  参考文献：
  名称：

  通过前手性烯醇的对映体分化质子化制备旋光性酮

  摘要：

  开发了2-苄基环己酮（3）的手性烯醇锂（2）的对映选择性质子化。2与作为手性质子源的（S）-α-羟基异己酸甲酯（15）的反应以高光学收率得到（R）-3。该反应可广泛用于制备各种α-取代的光学活性酮。

  DOI：

  10.1016/s0040-4039(00)92293-7

文献信息

• Substituted Pyrazinone Amides
  申请人：Benbow John William

  公开号：US20100184777A1

  公开（公告）日：2010-07-22

  The present invention provides compounds of Formula (I) that act as glucokinase activators; pharmaceutical compositions thereof; and methods of treating diseases, disorders, or conditions mediated by glucokinase. The variables R 1 , R 2 , R 3 and R 4 are as described herein.

  本发明提供了式(I)的化合物，这些化合物作为葡萄糖激酶激活剂；其药物组合物；以及治疗由葡萄糖激酶介导的疾病、障碍或状况的方法。变量R1、R2、R3和R4如本文所述。
• Heterocyclic derivatives as modulators of ion channels
  申请人：Martinborough Esther

  公开号：US20080027067A1

  公开（公告）日：2008-01-31

  The present invention relates to heterocyclic derivatives useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及用作离子通道抑制剂的杂环衍生物。该发明还提供了包括本发明化合物的药用可接受组合物，以及使用这些组合物治疗各种疾病的方法。
• Enantioselective total synthesis of (+)-rubrobramide, (+)-talaramide A, and (−)-berkeleyamide D by a skeletal diversification strategy
  作者：Kosaku Tanaka、Kenichi Kobayashi、Hiroshi Kogen

  DOI：10.1039/d1cc04290d

  日期：——

  A unified synthesis of (+)-rubrobramide, (+)-talaramide A, and (−)-berkeleyamide D was achieved from the vinylogous esters by a skeletal diversification strategy based on regioselective 5-exo or 6-endo cyclization. This report describes the first enantioselective total synthesis of (+)-rubrobramide and (+)-talaramide A. Additionally, synthetic spirocyclic lactam compounds, including (−)-berkeleyamide

  (+)-rubrobramide、(+)-talaramide A 和 (-)-berkeleyamide D 的统一合成是通过基于区域选择性 5- exo或 6- end环化的骨架多样化策略从乙烯基酯中实现的。本报告描述了 (+)-rubrobramide 和 (+)-talaramide A 的首次对映选择性全合成。 此外，合成的螺环内酰胺化合物，包括 (-)-berkeleyamide D，对潜在治疗的淀粉样蛋白-β 聚集显示出中等抑制活性阿尔茨海默病。
• Interconversion of (R) and (S)-α-hydroxy esters: precursors of (S) and (R)-o-benzyl-α-hydroxylamino acid esters of high optical purity
  作者：R.W. Feenstra、E.H.M. Stokkingreef、R.J.F. Nivard、H.C.J. Ottenheijm

  DOI：10.1016/s0040-4020(01)86063-4

  日期：1988.1

  (R)- and (S)-α-hydroxy esters 5 are interconverted via their triflates 6 in high chemical as well as optical yields by reaction with dimethylformamide. The same triflates are efficiently converted into N-hydroxy-α-amino acid derivatives 7 of high optical purity.

  （R）-和（S）-α-羟基酯5通过它们的三氟甲磺酸酯6与二甲基甲酰胺反应以高化学产率和光学产率被转化。相同的三氟甲磺酸酯被有效地转化为高光学纯度的N-羟基-α-氨基酸衍生物7。
• Solid-Phase Synthesis of Tetrahydropyridazinedione-Constrained Peptides
  作者：Chang Won Kang、Sujeewa Ranatunga、Matthew P. Sarnowski、Juan R. Del Valle

  DOI：10.1021/ol5026684

  日期：2014.10.17

  acids suitable for chemoselective incorporation into growing peptide chains. Acid-catalyzed cyclization to form the Tpd ring during cleavage affords the target peptidomimetics in good yield and purity. The scope of Tpd incorporation is demonstrated through the synthesis of constrained peptides featuring nucleophilic/electrophilic side chains and sterically encumbered α-substituted hydrazino acid residues

  报道了衍生自骨架胺化肽的四氢哒嗪-3,6-二酮 (Tpd) 肽模拟物的设计和固相合成。所描述的协议的特点是手性 α-肼酸的合成适用于化学选择性掺入不断增长的肽链。在裂解过程中酸催化环化形成 Tpd 环以良好的产率和纯度提供目标肽模拟物。Tpd 掺入的范围通过合成具有亲核/亲电侧链和空间位阻的 α-取代肼酸残基的受限肽来证明。