(Z)-isopropyl 2-acetyl-3-phenyl-2-propenoate | 613671-69-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-isopropyl 2-acetyl-3-phenyl-2-propenoate
• CAS: 613671-69-5
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: BJYYMIRRZQWYSR-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-isopropyl 2-acetyl-3-phenyl-2-propenoate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-Ethyl-6-methyl-4-phenyl-1,4-dihydro-pyridine-2,3,5-tricarboxylic acid 5-isopropyl ester
  参考文献：
  名称：

  Glucose-lowering in a db/db mouse model by dihydropyridine diacid glycogen phosphorylase inhibitors

  摘要：

  The synthesis of a series of novel dihdyropyridine diacid glycogen phosphorylase inhibitors is presented. SAR and functional assay data are discussed, along with the effect of a single inhibitor on blood glucose in a diabetic animal model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00798-4
• 作为产物：
  描述：

  乙酰乙酸异丙酯 、 苯甲醛 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 (Z)-isopropyl 2-acetyl-3-phenyl-2-propenoate
  参考文献：
  名称：

  Glucose-lowering in a db/db mouse model by dihydropyridine diacid glycogen phosphorylase inhibitors

  摘要：

  The synthesis of a series of novel dihdyropyridine diacid glycogen phosphorylase inhibitors is presented. SAR and functional assay data are discussed, along with the effect of a single inhibitor on blood glucose in a diabetic animal model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00798-4

文献信息

• Novel Knöevenagel-type reaction via titanium enolate derived from Ti(O-i-Pr)4 and diketene
  作者：Masahiko Hayashi、Norihiro Nakamura、Kohei Yamashita

  DOI：10.1016/j.tet.2004.06.018

  日期：2004.8

  Knöevenagel-type reaction between diketene and aldehydes proceeded in the presence of Ti(O-i-Pr)4. This reaction proceeded via titanium enolate derived from Ti(O-i-Pr)4 and diketene. As for the stereoselectivity of the products, E-isomers were produced predominantly in the case of aromatic aldehydes.

  双烯酮和醛之间的Knöevenagel型反应在Ti（O- i- Pr）4的存在下进行。该反应通过衍生自Ti（O - Pr）4和双烯酮的烯醇钛进行。至于产物的立体选择性，主要在芳族醛的情况下产生E-异构体。
• 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。