2-phenylethylmalonic acid | 3709-21-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenylethylmalonic acid
• 英文别名: 2-phenethylmalonic acid；Phenaethyl-malonsaeure；Propanedioic acid, (2-phenylethyl)-；2-(2-phenylethyl)propanedioic acid
• CAS: 3709-21-5
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: IUZIGXNXWJEZLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2917190090

反应信息

• 作为反应物：
  描述：

  2-phenylethylmalonic acid 生成 4-苯基丁酸
  参考文献：
  名称：

  Fischer,E.; Schmitz, Chemische Berichte, 1906, vol. 39, p. 2210

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 4-phenyl-2-((phenylsulfonyl)(pyridin-2-ylsulfinyl)methyl)butanoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 2-phenylethylmalonic acid
  参考文献：
  名称：

  由羧酸产生的碳自由基合成取代的丙二酸

  摘要：

  各种烯烃与通过Barton-酯的光解而产生的碳自由基的反应完成了适用于转化为相应丙二酸的加合物。

  DOI：

  10.1016/s0040-4039(00)60171-5

文献信息

• Discovery of Oxygen α-Nucleophilic Addition to α,β-Unsaturated Amides Catalyzed by Redox-Neutral Organic Photoreductant
  作者：Zi-Hong Luan、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/jacs.0c10707

  日期：2020.12.16

  addition) products. On the contrary, the formation of α-hydroxyl or alkoxyl amides through conjugate addition needs an α,β-inverse addition. Nevertheless, a regio-inversed nucleophilic α-addition of oxygen-centered nucleophiles to α,β-unsaturated carbonyl compounds still remains less explored because of the electronic mismatch. In this research, we discovered the first α-specific nucleophilic addition

  以氧为中心的亲核试剂与共轭受体的共轭加成是最强大的 CO 键形成反应之一。共轭加成通常发生在吸电子基团的 β 位碳上，导致形成稳定的碳负离子中间体，该中间体可以被质子或亲电试剂淬灭以形成 β-加成（即杂迈克尔加成）产品。相反，通过共轭加成形成α-羟基或烷氧基酰胺需要α，β-逆加成。然而，由于电子失配，以氧为中心的亲核试剂与 α,β-不饱和羰基化合物的区域反转亲核 α-加成仍然很少被探索。在这项研究中，我们发现了第一个 α 特异性亲核加成，β-不饱和酰胺与氧和氟亲核试剂。这种区域反转的亲核加成是通过新型氧化还原中性非供体受体有机光还原剂 (CBZ6) 的催化实现的。使用低至 0.5 mol% 的可见光光还原剂。还探讨了机械方面的见解。CBZ6 激发态的氧化电位在 -1.92 V（vs SCE）下获得，呈现出比代表性金属核或有机光氧化还原催化剂更强的还原电位。这一特征使 α,β-不饱和酰胺的 umpolung
• Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids
  作者：D. J. Abraham、P. E. Kennedy、A. S. Mehanna、D. C. Patwa、F. L. Williams

  DOI：10.1021/jm00374a006

  日期：1984.8

  small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds

  在本文中，我们进一步确立了两类小分子，即苄氧基和苯氧基酸的活性，它们是血红蛋白S（HbS）凝胶化的有效抑制剂。每个类别都有大量结构修饰，这证实了我们较早的工作，即发现含有带有连接的极性侧链的二卤代芳环的化合物具有最高的活性。我们还发现卤代芳族丙二酸衍生物非常活泼。将本文报道的化合物与我们实验室研究的其他抗胶凝剂进行了比较。关于四种衍生物的抗胶凝活性和结合位点及其对血红蛋白（Hb）功能的变构机制的影响进行了评论。
• α-Substituted norstatines as the transition-state mimic in inhibitors of multiple digestive vacuole malaria aspartic proteases
  作者：Kristina M. Orrling、Melissa R. Marzahn、Hugo Gutiérrez-de-Terán、Johan Åqvist、Ben M. Dunn、Mats Larhed

  DOI：10.1016/j.bmc.2009.06.065

  日期：2009.8

  compounds provided Ki values in the nanomolar range for all PM4, with a best value of 110 nM in PM4 from Plasmodium ovale. In addition, excellent selectivity over the closely related human aspartic protease Cathepsin D was achieved. The loss of affinity to Plasmodium falciparum PM4, which was experienced upon the move of the P1 substituent, was rationalized by the calculation of inhibitor–protein binding

  研究了含降nor素的纤溶酶抑制剂中P1侧链从β位置移动到α位置的影响，产生了两类新的含叔醇的α-苄基去甲他汀和α-苯基去甲他汀。设计，合成和评估了十二种α-取代的诺他汀类药物对所有四种导致人类疟疾的疟原虫的消化液中存在的纤溶酶II和纤溶酶IV直向同源物（PM4）的抑制作用。已开发出新的合成路线来生产所需的α-取代的诺他汀类药物，为纯立体异构体。最好的化合物为所有PM4提供的K i值都在纳摩尔范围内，椭圆疟原虫的PM4的最佳值为110 nM。另外，获得了与密切相关的人天冬氨酸蛋白酶组织蛋白酶D的优异的选择性。通过使用线性相互作用能法（LIE）计算抑制剂与蛋白质的结合亲和力，可以合理化丧失P1取代基后对恶性疟原虫PM4的亲和力。
• .beta.-thiopropionyl-aminoacid derivatives and their use as
  申请人：SmithKline Beecham p.l.c.

  公开号：US06048852A1

  公开（公告）日：2000-04-11

  A method of treatment of bacterial infections in humans or animals which comprises administering, in combination with a .beta.-lactam antibiotic, a therapeutically effective amount of an amino acid derivative of Formula (I) or a pharmaceutically acceptable salt, solvate or in vivo hydrolysable ester thereof, ##STR1## wherein: R is hydrogen, a salt forming cation or an in vivo hydrolysable ester-forming group; R.sub.1 is hydrogen, (C.sub.1-6)alkyl optionally substituted by up to three halogen atoms or by a mercapto, (C.sub.1-6)alkoxy, hydroxy, amino, nitro, carboxy, (C.sub.1-6)alkylcarbonyloxy, (C.sub.1-6)alkoxycarbonyl, formyl or (C.sub.1-6)alkylcarbonyl group, (C.sub.3-7)cycloalkyl, (C.sub.3-7)cycloalkyl(C.sub.2-6)alkyl, (C.sub.2-6)alkenyl, (C.sub.2-6)alkynyl, aryl, aryl(C.sub.1-6)alkyl, heterocyclyl or heterocyclyl(C.sub.1-6)alkyl; R.sub.2 is hydrogen, (C.sub.1-6)alkyl or aryl(C.sub.1-6)alkyl; R.sub.3 is hydrogen, (C.sub.1-6)alkyl optionally substituted by up to three halogen atoms, (C.sub.3-7)cycloalkyl, fused aryl(C.sub.3-7)cycloalkyl, (C.sub.3-7)cycloalkyl(C.sub.2-6)alkyl, (C.sub.2-6)alkenyl, (C.sub.2-6)alkynyl, aryl, aryl-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n, heterocyclyl or heterocyclyl-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n, where m is 0 to 3, n is 1 to 3, each R.sub.10 and R.sub.11 is independently hydrogen or (C.sub.1-4)alkyl and X is O, S(O).sub.x where x is 0-2, or a bond; R.sub.4 is hydrogen, or an in vivo hydrolysable acyl group; and R.sub.5 and R.sub.6 are independently hydrogen and (C.sub.1-6)alkyl or together represent (CH.sub.2).sub.p where p is 2 to 5. Some compounds are claimed per se.

  一种治疗人类或动物细菌感染的方法，包括与β-内酰胺类抗生素联合给药，给予公式(I)的氨基酸衍生物的治疗有效量或其药用可接受的盐、溶剂化合物或体内可水解酯的治疗有效量，其中：R为氢、形成盐的阳离子或体内可水解酯形成基团；R.sub.1为氢、(C.sub.1-6)烷基，可选地被高达三个卤素原子或巯基、(C.sub.1-6)烷氧基、羟基、氨基、硝基、羧基、(C.sub.1-6)烷基羰氧基、(C.sub.1-6)烷氧羰基、甲酰基或(C.sub.1-6)烷基羰基取代，(C.sub.3-7)环烷基，(C.sub.3-7)环烷基(C.sub.2-6)烷基，(C.sub.2-6)烯基，(C.sub.2-6)炔基，芳基，芳基(C.sub.1-6)烷基，杂环烷基或杂环烷基(C.sub.1-6)烷基；R.sub.2为氢，(C.sub.1-6)烷基或芳基(C.sub.1-6)烷基；R.sub.3为氢，(C.sub.1-6)烷基，可选地被高达三个卤素原子取代，(C.sub.3-7)环烷基，融合的芳基(C.sub.3-7)环烷基，(C.sub.3-7)环烷基(C.sub.2-6)烷基，(C.sub.2-6)烯基，(C.sub.2-6)炔基，芳基，芳基-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n，杂环烷基或杂环烷基-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n，其中m为0至3，n为1至3，每个R.sub.10和R.sub.11独立地为氢或(C.sub.1-4)烷基，X为O，S(O).sub.x，其中x为0-2，或键；R.sub.4为氢，或体内可水解的酰基；R.sub.5和R.sub.6独立地为氢和(C.sub.1-6)烷基，或一起代表(CH.sub.2).sub.p，其中p为2至5。一些化合物本身被要求。
• Synthesis of Cyclopentenones through Rhodium-Catalyzed C–H Annulation of Acrylic Acids with Formaldehyde and Malonates
  作者：Shuling Yu、Chao Hong、Zhanxiang Liu、Yuhong Zhang

  DOI：10.1021/acs.orglett.1c01569

  日期：2021.7.2

  An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C–H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a Na2CO3/MeOH solution. Excess formaldehyde and

  报道了一种有效的铑催化合成环戊烯酮的方案，该方案基于丙烯酸、甲醛和丙二酸酯通过乙烯基 C-H 活化的三组分反应。探索性研究表明，通过用 Na 2 CO 3 /MeOH 溶液处理各种烷基卤化物，可以顺利地实现所制备的环戊烯酮的 5-烷基化。过量的甲醛和丙二酸酯导致多组分反应，通过迈克尔加成得到多取代的环戊烯酮。