3-(2-bromobenzoyl)acrylic acid | 90767-22-9

• 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: 3-(2-bromobenzoyl)acrylic acid
• 英文别名: (E)-4-(2'-bromophenyl)-4-oxobut-2-enoic acid；(2E)-4-(bromophenyl)-4-oxo-2-butenoic acid；(E)-4-(2-bromophenyl)-4-oxobut-2-enoic acid
• CAS: 90767-22-9
• 化学式: C₁₀H₇BrO₃
• 分子量: 255.068
• InChiKey: HCOALQSLDQLCBD-AATRIKPKSA-N

物化性质

• 熔点：
  88-89 °C(Solvent: Carbon tetrachloride)
• 沸点：
  399.1±42.0 °C(Predicted)
• 密度：
  1.610±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-bromobenzoyl)acrylic acid 在 potassium carbonate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.75h， 生成 methyl 7-(2-bromophenyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-5-carboxylate
  参考文献：
  名称：

  尿嘧啶衍生的六和四氢吡啶并[2,3-d]嘧啶的有效合成

  摘要：

  6-氨基-1,3-二甲基尿嘧啶与 3-（杂）芳酰基丙烯酸及其甲酯的反应生成六氢吡啶并[2,3-d]嘧啶-5-羧酸或相应的甲酯，收率高至极好. 酸衍生物用 CAN 的一锅氧化伴随着脱羧作用得到四氢吡啶并[2,3-d]嘧啶，而用溴氧化导致形成四氢吡啶并[2,3-d]嘧啶-5-羧酸。在环境条件下通过 K2CO3 介导的空气氧化实现了甲基六氢吡啶并 [2,3-d]pyrimidine-5-carboxylates 的芳构化。

  DOI：

  10.1002/ejoc.201300683
• 作为产物：
  描述：

  2'-溴苯乙酮 、 乙醛酸 在 溶剂黄146 作用下， 生成 3-(2-bromobenzoyl)acrylic acid
  参考文献：
  名称：

  基于异氰化物的MCR：全氟烷基化吡喃并[3,4- c ]吡咯衍生物的非对映选择性级联合成

  摘要：

  含全氟烷基的吡喃并[3,4- c ]吡咯的高度非对映选择性合成是通过级联过程完成的，该过程涉及迈克尔加成，Passerini型反应，Mumm重排和羰基-狄尔斯-阿尔德反应。异氰酸酯，全氟烷-2-甲基丙烯酸甲酯和3-芳酰基（或杂芳基）丙烯酸的多米诺骨转化在室温下平稳进行，并导致形成具有高官能团相容性的高非对映选择性目标化合物，并具有良好的产率。

  DOI：

  10.1016/j.jfluchem.2021.109723

文献信息

• Studies on antirheumatic agents. 3-Benzoylpropionic acid derivatives.
  作者：KAZUYA KAMEO、KUNIO OGAWA、KIMIYO TAKESHITA、SHIRO NAKAIKE、KAZUYUKI TOMISAWA、KAORU SOTA

  DOI：10.1248/cpb.36.2050

  日期：——

  As part of the search for new antirheumatic agents, three types of 3-benzoylpropionic acid derivatives having a mercapto moiety in their structures were prepared, and tested for suppressing activity on adjuvant arthritis in Sprague-Dawley rats. A structure-activity relationship study showed that substitution on the phenyl ring contributed to the activity and the most favorable substituent was different in each type of derivative.

  作为寻找新型抗风湿药物的一部分，制备了三种含有巯基结构单元的3-苯甲酰丙酸衍生物，并测试了它们对Sprague-Dawley大鼠佐剂性关节炎的抑制活性。结构-活性关系研究表明，苯环上的取代基对活性有贡献，且每种衍生物中最有利的取代基各不相同。
• Benzoxazepine Compound
  申请人：Marui Shogo

  公开号：US20080227770A1

  公开（公告）日：2008-09-18

  A compound represented by the formula [1]: wherein ring A and ring B each represent an optionally substituted benzene ring; ring C represents an optionally further substituted aromatic ring; R 1 represents a lower alkyl group optionally substituted with an optionally substituted hydroxyl group; X 1a represents a bond or optionally substituted lower alkylene; X 1b represents a bond or optionally substituted lower alkylene; x 2 represents a bond, —O— or —S—; X 3 represents a bond or an optionally substituted divalent hydrocarbon group; Y represents an optionally esterified or amidated carboxyl group, or a salt thereof. The compound of the formula [I] is safer and has more potent lipid lowering activity such as squalene synthase inhibitory activity (cholesterol lowering activity) and triglyceride lowering activity, and thus it is a compound useful as an agent for preventing or treating hyperlipemia.

  一种由公式[1]表示的化合物：其中环A和环B分别表示可选择性取代的苯环；环C表示可选择性进一步取代的芳香环；R1表示可选择性取代的较低的烷基，其中还可选择性地取代有一个或多个羟基基团；X1a表示一个键或可选择性取代的较低的烷基烯；X1b表示一个键或可选择性取代的较低的烷基烯；x2表示一个键，-O-或-S-；X3表示一个键或可选择性取代的双价碳氢基团；Y表示可选择性酯化或酰胺化的羧基，或其盐。公式[I]的化合物更安全，并具有更强的降脂活性，如角鲨烷合酶抑制活性（降低胆固醇活性）和三酰甘油降低活性，因此它是一种有用的化合物，可用作预防或治疗高脂血症的药物。
• BENZOXAZEPINE COMPOUND
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1650201A1

  公开（公告）日：2006-04-26

  A compound represented by the formula [1]: wherein ring A and ring B each represent an optionally substituted benzene ring; ring C represents an optionally further substituted aromatic ring; R1 represents a lower alkyl group optionally substituted with an optionally substituted hydroxyl group; X1a represents a bond or optionally substituted lower alkylene; X1b represents a bond or optionally substituted lower alkylene; X2 represents a bond, -O- or -S-; X3 represents a bond or an optionally substituted divalent hydrocarbon group; Y represents an optionally esterified or amidated carboxyl group, or a salt thereof. The compound of the formula [I] is safer and has more potent lipid lowering activity such as squalene synthase inhibitory activity (cholesterol lowering activity) and triglyceride lowering activity, and thus it is a compound useful as an agent for preventing or treating hyperlipemia.

  由式 [1] 表示的化合物： 其中，环 A 和环 B 各代表一个任选取代的苯环；环 C 代表一个任选进一步取代的芳环；R1 代表一个任选被羟基取代的低级烷基；X1a 代表一个键或任选取代的低级亚烷基；X1b 代表一个键或任选取代的低级亚烷基；X2 代表一个键、-O- 或-S-；X3 代表一个键或任选取代的二价烃基；Y 代表一个任选酯化或酰胺化的羧基或其盐。式[I]化合物更安全，具有更强的降脂活性，如角鲨烯合成酶抑制活性（降胆固醇活性）和降甘油三酯活性，因此它是一种可用于预防或治疗高脂血症的化合物。
• EP1650201
  申请人：——

  公开号：——

  公开（公告）日：——
• CoA Adducts of 4-Oxo-4-phenylbut-2-enoates: Inhibitors of MenB from the <i>M. tuberculosis</i> Menaquinone Biosynthesis Pathway
  作者：Xiaokai Li、Nina Liu、Huaning Zhang、Susan E. Knudson、Huei-Jiun Li、Cheng-Tsung Lai、Carlos Simmerling、Richard A. Slayden、Peter J. Tonge

  DOI：10.1021/ml200141e

  日期：2011.11.10

  A high-throughput screen led to the discovery of 2-amino-4-oxo-4-phenylbutanoate inhibitors of the 1,4-dihydroxy-2-naphthoyl-CoA synthase (MenB) from the menaquinone biosynthesis pathway in Mycobacterium tuberculosis. However, these compounds are unstable in solution and eliminate to form the corresponding 4-oxo-4-phenylbut-2-enoates that then react with CoA in situ to form nanomolar inhibitors of MenB. The potency of these compounds results from interaction of the CoA adduct carboxylate with the MenB oxyanion hole, a conserved structural motif in the crotonase superfamily. 4-Oxo-4-chlorophenylbutenoyl methyl ester has minimum inhibitory concentrations of 0.6 and 1.5 mu g/mL against replicating and nonreplicating M. tuberculosis, respectively, and it is proposed that the methyl ester penetrates the cell where it is hydrolyzed and reacts with CoA to generate the active antibacterial. The CoA adducts thus represent an important foundation for the development of novel MenB inhibitors and suggest a general approach to the development of potent inhibitors of acyl-CoA binding enzymes.