(R)-2-bromo-3-phenylpropionic acid methyl ester | 73136-26-2

• 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-bromo-3-phenylpropionic acid methyl ester
• 英文别名: methyl (R)-2-bromo-3-phenylpropionate；methyl (2R)-2-bromo-3-phenylpropanoate
• CAS: 73136-26-2
• 化学式: C₁₀H₁₁BrO₂
• 分子量: 243.1
• InChiKey: OUCLVXLFVUBZAV-SECBINFHSA-N

物化性质

• 沸点：
  271.4±20.0 °C(Predicted)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-bromo-3-phenylpropionic acid methyl ester 在 palladium on activated charcoal sodium azide 、 hemin copolymer 1 、 氢气 作用下， 反应 18.0h， 生成 D-苯丙氨酸甲酯
  参考文献：
  名称：

  使用含血红素的新型聚合物负载试剂进行烷基卤的亲核取代反应

  摘要：

  通过悬浮共聚反应合成了一种由氯化血红素、二乙烯基苯和2-甲基-5-乙烯基吡啶组成的新型高分子试剂。伯、仲和叔烷基卤与氯化血红素共聚物与氰化物、叠氮化物和硫氰酸根离子的取代反应得到了令人满意的产率。根据立体化学研究，该反应机理被揭示为 SNi 型。氯化血红素共聚物不仅是具有功能性的聚合物负载试剂，而且还用于将产物与反应混合物分离。

  DOI：

  10.1246/bcsj.62.2562
• 作为产物：
  描述：

  D-苯丙氨酸 在 potassium bromide 、 sodium nitrite 作用下， 以 硫酸 为溶剂， 反应 1.0h， 生成 (R)-2-bromo-3-phenylpropionic acid methyl ester
  参考文献：
  名称：

  使用含血红素的新型聚合物负载试剂进行烷基卤的亲核取代反应

  摘要：

  通过悬浮共聚反应合成了一种由氯化血红素、二乙烯基苯和2-甲基-5-乙烯基吡啶组成的新型高分子试剂。伯、仲和叔烷基卤与氯化血红素共聚物与氰化物、叠氮化物和硫氰酸根离子的取代反应得到了令人满意的产率。根据立体化学研究，该反应机理被揭示为 SNi 型。氯化血红素共聚物不仅是具有功能性的聚合物负载试剂，而且还用于将产物与反应混合物分离。

  DOI：

  10.1246/bcsj.62.2562

文献信息

• 环氧基取代的氧代吡啶类衍生物、其制备方法 及其在医药上的应用
  申请人：江苏恒瑞医药股份有限公司

  公开号：CN107793396B

  公开（公告）日：2021-02-26

  本发明涉及环氧基取代的氧代吡啶类衍生物、其制备方法及其在医药上的应用。具体而言，本发明涉及一种通式(I)所示的环氧基取代的氧代吡啶类衍生物、其制备方法及含有该衍生物的药物组合物以及其作为治疗剂，特别是作为抑制凝血因子XIa(Faxtor XIa，简称FXIa)的抑制剂和在制备治疗血栓栓塞等疾病的药物中的用途，其中通式(I)中的各取代基的定义与说明书中的定义相同。
• A Substrate-Driven Approach to Determine Reactivities of α,β-Unsaturated Carboxylic Esters Towards Asymmetric Bioreduction
  作者：Gábor Tasnádi、Christoph K. Winkler、Dorina Clay、Nargis Sultana、Walter M. F. Fabian、Mélanie Hall、Klaus Ditrich、Kurt Faber

  DOI：10.1002/chem.201200990

  日期：2012.8.13

  The degree of CC bond activation in the asymmetric bioreduction of α,β‐unsaturated carboxylic esters by ene‐reductases was studied, and general recommendations to render these “borderline‐substrates” more reactive towards enzymatic reduction are proposed. The concept of “supported substrate activation” was developed. In general, an additional α‐halogenated substituent proved to be beneficial for enzymatic

  研究了烯还原酶对α，β-不饱和羧酸酯的不对称生物还原中CC键的活化程度，并提出了一般建议，以使这些“边界底物”对酶促还原反应更具活性。开发了“支持的底物活化”的概念。通常，另外一个α-卤代取代基被证明对酶活性有益，而β-烷基或β-芳基取代基对非卤代底物的反应性有害，而α-氰基几乎没有作用。发现酯官能度的醇部分对反应速率具有强烈影响。总体而言，活动取决于空间效果和电子效果。
• Enantioselective protonation of α-hetero carboxylic acid-derived ketene disilyl acetals under chiral ionic Brønsted acid catalysis
  作者：Daisuke Uraguchi、Tomohito Kizu、Yuki Ohira、Takashi Ooi

  DOI：10.1039/c4cc06081d

  日期：——

  P-Spiro chiral diaminodioxaphosphonium ion discriminates the enantiofaces of α-halo and alkoxy carboxylic acid-derived ketene disilyl acetals by the recognition of the electronic difference between two substituents of the ketene disilyl acetal in the proton-transfer event.

  P-Spiro手性二氨基二氧磷离子通过识别酮二硅基乙酸酯的两个取代基之间的电子差异，在质子转移事件中区分α-卤代和烷氧基羧酸衍生的酮二硅基乙酸酯的对映面。
• Synthesis and activity of HIV protease inhibitors
  作者：Patrick Garrouste、Macek Pawlowski、Thierry Tonnaire、Sames Sicsic、Pascal Dumy、Eve de Rosny、Michèle Reboud-Ravaux、Pierre Fulcrand、Jean Martinez

  DOI：10.1016/s0223-5234(98)80043-3

  日期：1998.6

  We report here the synthesis and activity of HIV protease inhibitors. Ln the first stage hydrophobic compounds incorporating a 'carba' bond surrogate or a beta-homologated residue were synthesized. Secondly, we synthesized cyclic compounds in which we incorporated 2-quinoline carboxylic acid in the P3 position and the amino-hydroxyindane moiety in the P'3. The last part of this work was dedicated to a structure/activity study of a peptide substrate. These modifications allowed us to work up the synthesis of new pseudopeptide bonds: amino-amide and hydroxy-amide, Compounds with activity in the micromolar range were actually a starting point for the synthesis of new protease inhibitors. (C) Elsevier, Paris.
• Direct Catalytic Asymmetric Aldol Reaction
  作者：Naoki Yoshikawa、Yoichi M. A. Yamada、Jagattaran Das、Hiroaki Sasai、Masakatsu Shibasaki

  DOI：10.1021/ja990031y

  日期：1999.5.1

  The direct catalytic asymmetric aldol reaction using aldehydes and unmodified ketones is described for the first time herein. This reaction was first found to be promoted by 20 mol % of anhydrous (R)-LLB (L = lanthanum, L = lithium, B = (R)-binaphthol moiety) at -20 OC, giving a variety of aldol products in ee's ranging from 44 to 94%. This asymmetric reaction has been greatly improved by developing a new heteropolymetallic asymmetric catalyst [(R)-LLB, KOH, and H2O]. Using 3-8 mol % of this catalyst, a variety of direct catalytic asymmetric aldol reactions were again found to proceed smoothly, affording aldol products in ee's ranging from 30 to 93% and in good to excellent yields. Interestingly, the use of this new heteropolymetallic asymmetric catalyst has realized a diastereoselective and enantioselective aldol reaction using cyclopentanone for the first time. It is also noteworthy that a variety of aldehydes, including hexanal, can be utilized for the current direct catalytic asymmetric aldol reaction. Chiral aldehydes containing alpha-hydrogen including (S)-hydrocinnamaldehyde-alpha-d have been found to produce the corresponding aldol products with negligible racemization (0-4%) at the a-position One of the aldol products has been successfully converted to the key synthetic intermediates of epothilone A and bryostatin 7. The possible structure of the heteropolymetallic catalyst is also discussed. Finally, mechanistic studies have revealed a characteristic reaction pathway, namely that the reaction is kinetically controlled and the rate-determining step is the deprotonation of the ketone. This is consistent with the fact that the reaction rate is independent of the concentration of the aldehyde.