2-benzyl-3-hydroxypropanoic acid | 6811-98-9

• 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-benzyl-3-hydroxypropanoic acid
• 英文别名: (RS)-2-hydroxymethyl-3-phenylpropionic acid；BHPA
• CAS: 6811-98-9
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: RDUHFHDKXQBHMH-UHFFFAOYSA-N

物化性质

• 熔点：
  60-62 °C
• 沸点：
  352.5±30.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-benzyl-3-hydroxypropanoic acid 在 sodium hydroxide 、 phosphate buffer 、 乙酰氯 、 α-chymotrypsin 作用下， 反应 42.0h， 生成 (S)-2-benzyl-3-hydroxypropanoic acid methyl ester
  参考文献：
  名称：

  Cleavage of β-lactone ring by serine protease. Mechanistic implications

  摘要：

  Both enantiomers of 3-benzyl-2-oxctanone (1) were found to be slowly hydrolyzed substrates of a-chymotrypsin having k(cat) values of 0.134 +/- 0.008 and 0.105 +/- 0.004min(-1) for (R)-1 and (S)-1, respectively, revealing that alpha-CT is virtually unable to differentiate the enantiomers in the hydrolysis of 1. The initial step to form the acyl-enzyme intermediate by the attack of Ser-195 hydroxyl on the beta-lactone ring at the 2-position in the hydrolysis reaction may not be enzymatically driven, but the relief of high ring strain energy of beta-lactone may constitute a major driving force. The deacylation step is also attenuated, which is possibly due to the hydrogen bond that would be formed between the imidazole nitrogen of His-57 and the hydroxyl group generated during the acylation in the case of (R)-1, but in the alpha-CT catalyzed hydrolysis of (S)-1 the imidazole nitrogen may form a hydrogen bond with the ester carbonyl oxygen. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00108-6
• 作为产物：
  描述：

  methyl 2-(acetoxymethyl)-3-phenylprop-2-enoate 在 palladium-carbon 盐酸 、 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 正己烷 、 水 、 乙酸乙酯 为溶剂， 生成 2-benzyl-3-hydroxypropanoic acid
  参考文献：
  名称：

  Method for producing optically active phenylpropionic acid derivative

  摘要：

  具有光学活性的N-(S-2-乙酰硫甲基-1-氧代-3-苯基丙基)-甘氨酸苄酯可作为一种脑啡肽抑制剂或ACE抑制剂，在工业上可以以低成本生产，其方法包括将具有光学活性的2-羟甲基-3-苯基丙酸和甘氨酸苄酯进行缩合，随后将羟基转化为一个消除基团，并用乙酰硫基团替代消除基团。

  公开号：

  US06031121A1

文献信息

• 14-Membered cyclodepsipeptides with alternating β-hydroxy and α-amino acids by cyclodimerization
  作者：Boyan Iliev、Anthony Linden、Roland Kunz、Heinz Heimgartner

  DOI：10.1016/j.tet.2005.11.002

  日期：2006.2

  cyclodimer 10. In all cases, when starting with racemic material, only the trans-substituted cyclodepsipeptides were isolated. Simple molecular modeling revealed that the formation of the cyclodimer is thermodynamically slightly more favorable than that of the cyclomonomer. The proposal that cyclodimer formation is preferred because of the presence of intramolecular H-bonds could not be confirmed by X-ray

  描述了在“直接酰胺环化”（DAC）条件下1型β-羟基酰胺的环二聚（孪生）。尽管其他偶联方法也可得出中等结果，但通过DAC可获得最佳收率，环二聚体10可达88％。在所有情况下，当从外消旋物质开始时，仅分离出反式取代的环二肽。简单的分子模型表明，环二聚体的形成在热力学上比环聚单体的形成稍微更有利。由于分子内氢键的存在，优选形成环二聚体的提议不能通过X射线晶体学证实。还研究了取代基在氨基酸和羟基酸部分中的影响。结果表明，仅当羟基酸部分被α，α-二取代时，环二聚作用才成功。
• Direct β-Selective Hydrocarboxylation of Styrenes with CO₂ Enabled by Continuous Flow Photoredox Catalysis
  作者：Hyowon Seo、Aofei Liu、Timothy F. Jamison

  DOI：10.1021/jacs.7b05942

  日期：2017.10.11

  The direct β-selective hydrocarboxylation of styrenes under atmospheric pressure of CO2 has been developed using photoredox catalysis in continuous flow. The scope of this methodology was demonstrated with a range of functionalized terminal styrenes, as well as α-substituted and β-substituted styrenes.

  已经在连续流动中使用光氧化还原催化开发了在 CO2 大气压下苯乙烯的直接 β-选择性加氢羧化反应。该方法的范围通过一系列官能化的末端苯乙烯以及 α-取代和 β-取代的苯乙烯进行了证明。
• 인자 ＸＩａ 억제 활성을 가지는 신규한 화합물
  申请人：LEGOCHEM BIOSCIENCES, INC. 주식회사 레고켐 바이오사이언스(120060498483) Corp. No ▼ 160111-0206866BRN ▼314-81-82268

  公开号：KR20150136294A

  公开（公告）日：2015-12-07

  본 발명은 인자 XIa (Factor XIa, FXIa)에 대해 억제 활성을 가지는 약리학적 유효량의 하기 화학식 1로 표시되는 신규한 화합물 및 이의 제조방법과, 이의 약제학적으로 허용되는 염, 수화물, 용매화물, 이성질체 및 프로드럭을 유효성분으로 함유하는 혈액 응고 예방 및 각종 혈전증의 치료를 위한 약제 조성물에 관한 것이다. (1) 상기 화학식 1에서, A, L, X, Y, Z 및 n은 본 명세서에 정의된 바와 동일하다.

  This is the translation of the text you provided: This invention relates to a novel compound represented by the chemical formula 1 having pharmacologically effective amounts inhibiting the activity of Factor XIa (Factor XIa, FXIa), its preparation method, and pharmaceutical compositions for the prevention of blood coagulation and the treatment of various thrombotic disorders, comprising the compound as an active ingredient. In the chemical formula 1, A, L, X, Y, Z, and n are as defined in this specification.
• Photoinduced Hydrocarboxylation via Thiol-Catalyzed Delivery of Formate Across Activated Alkenes
  作者：Sara N. Alektiar、Zachary K. Wickens

  DOI：10.1021/jacs.1c07562

  日期：2021.8.25

  Herein we disclose a new photochemical process to prepare carboxylic acids from formate salts and alkenes. This redox-neutral hydrocarboxylation proceeds in high yields across diverse functionalized alkene substrates with excellent regioselectivity. This operationally simple procedure can be readily scaled in batch at low photocatalyst loading (0.01% photocatalyst). Furthermore, this new reaction can

  在此，我们公开了一种从甲酸盐和烯烃制备羧酸的新光化学方法。这种氧化还原中性的加氢羧化反应在多种功能化烯烃底物上以高产率进行，具有优异的区域选择性。这种操作简单的程序可以很容易地在低光催化剂负载（0.01% 光催化剂）下批量缩放。此外，这种新反应可以利用市售的甲酸盐碳同位素来直接合成同位素标记的羧酸。机理研究支持涉及硫醇催化自由基链过程的工作模型，其中来自甲酸盐的原子通过CO 2 •–作为关键的反应中间体传递穿过烯烃底物。
• [EN] SERINE/THREONINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE SÉRINE/THRÉONINE KINASE
  申请人：GENENTECH INC

  公开号：WO2015085007A1

  公开（公告）日：2015-06-11

  Compounds having the formula I wherein R1, X1, X2, X3 and X4 as defined herein are inhibitors of ERK kinase. Also disclosed are compositions and methods for treating hyperproliferative disorders.

  具有公式I的化合物，在此处定义的R1、X1、X2、X3和X4为ERK激酶的抑制剂。还公开了用于治疗过度增殖性疾病的组合物和方法。