2-hydroxymethyl-2-methyl-3-phenylpropanoic acid | 594837-44-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-hydroxymethyl-2-methyl-3-phenylpropanoic acid
• 英文别名: β-Phenyl-β-hydroxy-pivalinsaeure；2-benzyl-3-hydroxy-2-methyl-propionic acid；2-benzyl-3-hydroxy-2-methylpropanoic acid；2-Benzyl-3-hydroxy-2-methylpropanoic acid
• CAS: 594837-44-2
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: MJQBDRKBBFVTCN-UHFFFAOYSA-N

物化性质

• 熔点：
  109-110 °C
• 沸点：
  355.2±30.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-hydroxymethyl-2-methyl-3-phenylpropanoic acid 在 氢溴酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (R)-2-acetylsulfanylmethyl-2-methyl-3-phenylpropanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of α,α-disubstituted-3-mercaptopropanoic acids as inhibitors for carboxypeptidase A and implications with respect to enzyme inhibitor design

  摘要：

  2-Ethyl-2-meth% 1-3-mercaptopropanoic acid (6) and 2-benzyl-2-methyl-3-mercaptopropanoic acid (7) were synthesized and evaluated as inhibitors for carboxypeptidase A (CPA), a prototypical zinc protease with the expectation that the binding affinities of these inhibitors would be augmented over those of 2-ethyl-3-methylsuccinic acid (2) and 2-benzyl-3-methylsuccinic acid (3), respectively, in light of the fact that the sulfhydryl group is a better zinc coordinating moiety than the carboxylate group. Contrary to the expectation. however. the inhibitory potency of 6 was not improved and that of 7 was rather attenuated by the replacement. A probable explanation for the unexpected results is offered. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.017
• 作为产物：
  描述：

  N-[2,2-dimethyl-3-phenylpropanoyl]-S-methyl-S-2-pyridylsulfoximine 在 盐酸 、 碘苯二乙酸 、 水 、 palladium diacetate 作用下， 反应 38.0h， 生成 2-hydroxymethyl-2-methyl-3-phenylpropanoic acid
  参考文献：
  名称：

  Pd(II)-Catalyzed Primary-C(sp³)–H Acyloxylation at Room Temperature

  摘要：

  With the aid of a novel S-methyl-S-2-pyridyl-sulfoximine (MPyS) directing group (DG), the unactivated primary beta-C(sp(3))-H bond of MPyS-N-amides oxidizes at room temperature. The catalytic conditions are applicable to the diacetoxylation of primary beta,beta'-C(sp(3))-H bonds, and the carboxylic acid solvent is pivotal in the formation of the C-O bond. The MPyS-DG cleaves from the oxidation products and is recovered. This method provides convenient access to alpha,alpha'-disubstituted-beta-hydroxycarboxylic acids.

  DOI：

  10.1021/ol301579q

文献信息

• Selective Reductions of Cyclic 1,3-Diesters by Using SmI₂and H₂O
  作者：Karl D. Collins、Juliana M. Oliveira、Giuditta Guazzelli、Brice Sautier、Sara De Grazia、Hiroshi Matsubara、Madeleine Helliwell、David J. Procter

  DOI：10.1002/chem.201000632

  日期：2010.9.3

  SmI2/H2O reduces cyclic 1,3‐diesters to 3‐hydroxyacids with no over reduction. Furthermore, the reagent system is selective for cyclic 1,3‐diesters over acyclic 1,3‐diesters, and esters. Radicals formed by one‐electron reduction of the ester carbonyl group have been exploited in intramolecular additions to alkenes. The ketal unit and the reaction temperature have a marked impact on the diastereoselectivity

  SmI 2 / H 2 O可以将环状1,3-二酯还原为3-羟基酸，且不会过度还原。此外，该试剂系统对环状1,3-二酯的选择要高于非环状1,3-二酯和酯的选择。通过单电子还原酯羰基形成的自由基已在分子内加成烯烃中得到利用。缩酮单元和反应温度对环化的非对映选择性具有显着影响。当起始环二酯中存在两个烯烃并导致形成两个具有良好立体控制性的环和四个立体中心时，可能会发生级联级联反应。
• Guazzelli, Giuditta; Grazia, Sara De; Collins, Karl D., Journal of the American Chemical Society, 2009, vol. 131, p. 7214 - 7215
  作者：Guazzelli, Giuditta、Grazia, Sara De、Collins, Karl D.、Matsubara, Hiroshi、Spain, Malcolm、Procter, David J.

  DOI：——

  日期：——