isopropyl 3',4',5'-trimethoxycinnamate | 1287301-97-6

• 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: isopropyl 3',4',5'-trimethoxycinnamate
• 英文别名: Propan-2-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate；propan-2-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate
• CAS: 1287301-97-6
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: DISQENNSXSAVRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  isopropyl 3',4',5'-trimethoxycinnamate 、 2-氨基苯硫醇 在 L-精氨酸 、 四丁基溴化铵 、 水 、 1-丁基-3-甲基咪唑溴盐 作用下， 反应 18.0h， 以94%的产率得到isopropyl 3-((2-aminophenyl)thio)-3-(3,4,5-trimethoxyphenyl)propanoate
  参考文献：
  名称：

  L-精氨酸-[bmim] Br在级联脱羧Knoevenagel-Thia-Michael加成反应中的协同协同作用：绿色方法实现C-S键形成并原位生成未活化的α，β-不饱和酯

  摘要：

  在本报告中，首次实现了L-精氨酸和[bmim] Br的协同结合，从而通过级联噻吩-迈克尔加成反应从芳族醛，丙二酸酯和硫醇逐步经济地合成β-芳基-β-硫烷基酯。在无金属和无酸/无碱条件下原位形成未活化的β-芳基-α，β-不饱和酯的反应（通过脱羧Knoevenagel反应）。此外，催化体系的克级可扩展性和可回收性（最多5个循环）使我们的一锅两步方案比传统的两步方法更经济高效，并且对于级联C-C和C-S键的形成具有综合吸引力。催化系统的协同相互作用 e。带有[bmim] Br的L-精氨酸已通过NMR（1 H和13 C）研究进行了探测。

  DOI：

  10.1002/adsc.201801150
• 作为产物：
  描述：

  3,4,5-三甲氧基肉桂酸 、 异丙醇 在 硫酸 作用下， 以95%的产率得到isopropyl 3',4',5'-trimethoxycinnamate
  参考文献：
  名称：

  Novel natural product-based cinnamates and their thio and thiono analogs as potent inhibitors of cell adhesion molecules on human endothelial cells

  摘要：

  In the present study, we report the design and synthesis of novel analogs of cinnamates, thiocinnamates and thionocinnamates and evaluated the potencies of these analogs to inhibit TNF-alpha induced ICAM-1 expression on human endothelial cells. By using whole cell-ELISA, our screening data demonstrated that ethyl 3',4',5'-trimethoxythionocinnamate (ETMTC) is the most potent inhibitor of TNF-alpha induced ICAM-1, VCAM-1 and E-selectin. As functional consequences, ETMTC abrogated TNF-alpha induced adhesion of neutrophils to the endothelial monolayer. Structure activity relationship studies revealed the critical role of the chain-length of the alkyl group in the alcohol moiety, number of methoxy groups in the aromatic ring of the cinnamoyl moiety and the presence of the alpha, beta- C-C double bond in the thiocinnamates and thionocinnamates. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.008

文献信息

• Novel natural product-based cinnamates and their thio and thiono analogs as potent inhibitors of cell adhesion molecules on human endothelial cells
  作者：Sarvesh Kumar、Brajendra K. Singh、Pragya Arya、Shashwat Malhotra、Rajesh Thimmulappa、Ashok K. Prasad、Erik Van der Eycken、Carl E. Olsen、Anthony L. DePass、Shyam Biswal、Virinder S. Parmar、Balaram Ghosh

  DOI：10.1016/j.ejmech.2011.09.008

  日期：2011.11

  In the present study, we report the design and synthesis of novel analogs of cinnamates, thiocinnamates and thionocinnamates and evaluated the potencies of these analogs to inhibit TNF-alpha induced ICAM-1 expression on human endothelial cells. By using whole cell-ELISA, our screening data demonstrated that ethyl 3',4',5'-trimethoxythionocinnamate (ETMTC) is the most potent inhibitor of TNF-alpha induced ICAM-1, VCAM-1 and E-selectin. As functional consequences, ETMTC abrogated TNF-alpha induced adhesion of neutrophils to the endothelial monolayer. Structure activity relationship studies revealed the critical role of the chain-length of the alkyl group in the alcohol moiety, number of methoxy groups in the aromatic ring of the cinnamoyl moiety and the presence of the alpha, beta- C-C double bond in the thiocinnamates and thionocinnamates. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synergistic Cooperative Effect of L-Arginine-[bmim]Br in Cascade Decarboxylative Knoevenagel-Thia-Michael Addition Reactions: Green Approach Towards C−S Bond Formation with In Situ Generated Unactivated α,β-Unsaturated Ester
  作者：Richa Singh、Yogesh Thopate、Danish Equbal、Arun K. Sinha

  DOI：10.1002/adsc.201801150

  日期：2018.11.16

  β‐aryl‐β‐sulfanyl esters from aromatic aldehyde, malonate and thiol via cascade thia‐Michael addition reaction on in situ formed unactivated β‐aryl‐α,β‐unsaturated esters (via decarboxylative Knoevenagel reaction) under metal‐and acid/base‐free conditions. Furthermore, the gram scalability and recyclability of the catalytic system (up to 5 cycles) makes our one‐pot two‐step protocol more economically efficient and

  在本报告中，首次实现了L-精氨酸和[bmim] Br的协同结合，从而通过级联噻吩-迈克尔加成反应从芳族醛，丙二酸酯和硫醇逐步经济地合成β-芳基-β-硫烷基酯。在无金属和无酸/无碱条件下原位形成未活化的β-芳基-α，β-不饱和酯的反应（通过脱羧Knoevenagel反应）。此外，催化体系的克级可扩展性和可回收性（最多5个循环）使我们的一锅两步方案比传统的两步方法更经济高效，并且对于级联C-C和C-S键的形成具有综合吸引力。催化系统的协同相互作用 e。带有[bmim] Br的L-精氨酸已通过NMR（1 H和13 C）研究进行了探测。