methyl 2-acetyl-3-(2-thienyl)acrylate | 136814-19-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 2-acetyl-3-(2-thienyl)acrylate
• 英文别名: methyl 2-(thienylmethylene)acetoacetate；methyl 2-acetyl-3-(thien-2-yl)acrylate；methyl (2Z)-3-oxo-2-(thiophen-2-ylmethylidene)butanoate
• CAS: 136814-19-2
• 化学式: C₁₀H₁₀O₃S
• 分子量: 210.254
• InChiKey: XFNYIZNTVJXDQI-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl N-(2-hydroxyethylamino)crotonate 、 methyl 2-acetyl-3-(2-thienyl)acrylate 以 甲醇 为溶剂， 反应 24.0h， 以25%的产率得到dimethyl 7-(2-thienyl)-5,8a-dimethyl-2,3,7,8-tetrahydro-7H-oxazolo<3,2-a>pyridin-6,8-dicarboxylate
  参考文献：
  名称：

  2,3,8,8a-Tetrahydro-7H-oxazolo[3,2-a]pyridine: A new heterocyclic system

  摘要：

  Compounds with the previously unreported skeleton of 2,3,8,8a-tetrahydro-7H-oxazolo [3,2-a]pyridine were prepared by reactions between alpha,beta-unsaturated ketones or aldehydes and N-hydroxyethylenamines of acetoacetate esters. Other compounds like 1,4-dihydropyridines, aminocyclohexene and cyclohexadiene derivatives were also formed as minor products.

  DOI：

  10.1016/s0040-4020(01)86577-7
• 作为产物：
  描述：

  哌啶 、 2-噻吩甲醛 、 乙酰乙酸甲酯 在 溶剂黄146 作用下， 以 苯 为溶剂， 生成 methyl 2-acetyl-3-(2-thienyl)acrylate
  参考文献：
  名称：

  Polyazaheterocycle compounds

  摘要：

  一种多氮杂环化合物，其化学式为：##STR1## 或其药学上可接受的盐，其中每个符号如规范中所定义。该化合物表现出钙拮抗和/或钙激动活性。

  公开号：

  US04918074A1

文献信息

• Enantioselective Catalytic Hantzsch Dihydropyridine Synthesis
  作者：Xinyue Hu、Long Chen、Hongye Li、Qifan Xu、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/acscatal.2c05888

  日期：2023.5.19

  obtained through the asymmetric catalytic cascade reaction between 3-amino-2-butenoates and (Z)-2-arylidene-3-oxobutanoates. The N,N′-dioxide/NiII or NdIII complex catalysts were disclosed to be efficient, furnishing a variety of the products, including drugs like nitrendipine, nimodipine, and felodipine, in high yields (up to 99% yield) with excellent enantioselectivities (up to 99% ee). Two enantiomers

  通过 3-amino-2-butenoates 和 ( Z )-2-arylidene-3-oxobutanoates 之间的不对称催化级联反应，获得了带有不同酯基的光学富集的 Hantzsch 二氢吡啶。N ，N'-二氧化物/Ni II或 Nd III络合物催化剂据称是高效的，以高产率（高达 99% 的产率）和优异的性能提供多种产品，包括尼群地平、尼莫地平和非洛地平等药物对映选择性（高达 99% ee）。通过两种反应物酯基的交换，很容易得到产物的两种对映异构体。此外，还通过氧化过程提供了轴向手性 4-芳基吡啶。
• POLYAZAHETEROCYCLIC DERIVATIVES, PROCESS FOR THEIR PREPARATION, AND PHARMACEUTICAL COMPOSITION
  申请人：Yoshitomi Pharmaceutical Industries, Ltd.

  公开号：EP0183848A1

  公开（公告）日：1986-06-11

  Polyazaheterocyclic derivatives represented by the general formula (1), pharmaceutically acceptable salts thereof process for their preparation, and pharmaceutical compositions containing them. In the general formula, R represents hydrogen, lower alkyl, cycloalkyl, furyl, thienyl, pyridyl, or phenyl optionally having one to two substituents of halogen, tower alkyl, trifluoromethyl, alkoxy, aralkyloxy, alkylthio, aralkylthio, acyl, hydroxy, amino, nitro or cyano; R1 represents hydrogen, cyano, carbamoyl, carboxyl, alkoxycarbonyl having optionally one to two substituents of alkoxy, cyano, - N(Ra)(Rb) (wherein Ra and Rb each represents alkyl or aralkyl or, when taken together, represent a 5 to 7- membered heterocyclic ring), nitro, phenyl or heteroaryl, or alkanoyl; R2 represents lower alkyl, hydroxyalkyl, acetoxyalkyl, haloalkyl, dihaloalkyl, trifluoromethyl, alkoxyalkyl, di-alkoxymethyl, lower alkylcarbamoyloxyalkyl, lower alkyl-thiocarbamoyloxyalkyl, formyl, hydroxyiminomethyl or cyano; and X, Y, and Z each represents a member of ring A and each represents N or CH. These compounds possess hypotensive, coronary vasodilating, cerebrovasodilating and cardiotonic effects, and an effect of preventing peroxidation of lipid, and are useful as agents for prevention and treatment of circulatory organ diseases.

  通式(1)代表的多氮杂环衍生物、其药学上可接受的盐及其制备工艺，以及含有它们的药物组合物。通式中，R 代表氢、低级烷基、环烷基、呋喃基、噻吩基、吡啶基或苯基，可任选具有一至两个卤素、塔烷基、三氟甲基、烷氧基、芳基氧基、烷硫基、芳基硫基、酰基、羟基、氨基、硝基或氰基取代基；R1 代表氢、氰基、氨基甲酰基、羧基、烷氧基羰基（可选择具有一至两个烷氧基、氰基、-N(Ra)(Rb)取代基）（其中 Ra 和 Rb 各自代表烷基或芳烷基，或共同代表 5 至 7 位杂环）、硝基、苯基或杂芳基或烷酰基；R2 代表低级烷基、羟基烷基、乙酰氧基烷基、卤代烷基、二卤代烷基、三氟甲基、烷氧基烷基、二烷氧基甲基、低级烷基氨基甲酰氧基烷基、低级烷基-硫代氨基甲酰氧基烷基、甲酰基、羟基亚氨基甲基或氰基；以及 X、Y 和 Z 各自代表环 A 的一个成员，且各自代表 N 或 CH。这些化合物具有降血压、扩张冠状血管、扩张脑血管和强心作用，以及防止脂质过氧化的作用，可作为预防和治疗循环器官疾病的药物。
• Optical active 1,4-dihydropyridine derivates
  申请人：FUJIREBIO INC.

  公开号：EP0403957A2

  公开（公告）日：1990-12-27

  Optical active 1,4-dihydropyridine derivatives of formula: wherein Ar¹ represents an aromatic hydrocarbon group or an aromatic heteromonocyclic or heterobicyclic group containing therein 1 to 3 atoms selected from the group consisting of oxygen, sulfur and nitrogen; R¹ represents a hydrocarbon group which may have one or more substituents; A represents (i) a straight chain or branched chain unsaturated hydrocarbon group, (ii) a cyclic unsaturated hydrocarbon group, or (iii) a group selected from the group consisting of -R-O-N=CH-, -R-N=N-, -R-CH=N- and -R-N=CH-, in which R is an alkylene group having 1 to 6 carbon atoms; B represents an alkylene or alkenylene group having 1 to 3 carbon atoms, which may have a substituent; Ar² represents an aromatic hydrocarbon group or a heterocyclic group; Ar³ represents a heterocyclic group which may have one or more substituents; and n is 0 or 1, and * indicates an optically active cite.

  式中具有光学活性的 1,4-二氢吡啶衍生物： 其中 Ar¹ 代表芳香烃基团或芳香杂单环基团或杂环基团，其中包含 1 至 3 个原子，这些原子选自由氧、硫和氮组成的组；R¹ 代表烃基团，可以有一个或多个取代基；A 代表(i)直链或支链不饱和烃基，(ii)环状不饱和烃基，或(iii)选自-R-O-N=CH-、-R-N=N-、-R-CH=N-和-R-N=CH-的基团，其中 R 是具有 1 至 6 个碳原子的亚烷基；Ar² 代表芳香烃基团或杂环基团；Ar³ 代表杂环基团，可带有一个或多个取代基；n 为 0 或 1，* 表示光学活性引物。
• US4918074A
  申请人：——

  公开号：US4918074A

  公开（公告）日：1990-04-17
• US5286869A
  申请人：——

  公开号：US5286869A

  公开（公告）日：1994-02-15