(E)-4-(3,5-dimethoxyphenyl)-3-(methoxycarbonyl)but-3-enoic acid | 77729-55-6

• 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: (E)-4-(3,5-dimethoxyphenyl)-3-(methoxycarbonyl)but-3-enoic acid
• 英文别名: 2-[1-(3,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-succinic acid 1-methyl ester；(E)-4-(3,5-dimethoxyphenyl)-3-methoxycarbonylbut-3-enoic acid
• CAS: 77729-55-6
• 化学式: C₁₄H₁₆O₆
• 分子量: 280.277
• InChiKey: DQEQNHNAMSBSQL-ONNFQVAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-4-(3,5-dimethoxyphenyl)-3-(methoxycarbonyl)but-3-enoic acid 在 甲醇 、 potassium acetate 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.25h， 生成 4-羟基-5,7-二甲氧基-2-萘羧酸甲酯
  参考文献：
  名称：

  Synthetic Approach to Hypoxyxylerone, Novel Inhibitor of Topoisomerase I

  摘要：

  [GRAPHICS]A potential route to the topoisomerase I inhibitor hypoxyxylerone is demonstrated by a highly convergent synthesis of the penta(O-methyl) derivative. The key step in the approach is an anionic homo-Fries rearrangement, little used to date in natural product synthesis and employed here for the first time with a dinaphthalenic substrate, to access the pentacyclic system of hypoxyxylerone.

  DOI：

  10.1021/ol026454d
• 作为产物：
  描述：

  2-tert-Butoxycarbonyl-1-methoxycarbonylethylidene(triphenyl)phosphorane 在 三氟乙酸 作用下， 以 苯 为溶剂， 反应 48.17h， 生成 (E)-4-(3,5-dimethoxyphenyl)-3-(methoxycarbonyl)but-3-enoic acid
  参考文献：
  名称：

  Rizzacasa, Mark A.; Sargent, Melvyn V., Australian Journal of Chemistry, 1987, vol. 40, # 10, p. 1737 - 1743

  摘要：

  DOI：

文献信息

• A highly regio- and stereoselective Pd-catalyzed electrocarboxylation of Baylis-Hillman acetates: An interesting switchable regioselectivity based on electrode material
  作者：Satyanarayana Tummanapalli、Kali Charan Gulipalli、Srinivas Endoori、Srinu Bodige、Anil Kumar Pommidi、Srinivas Medaboina、Swathi Rejinthala、Suresh Choppadandi、Ravi Boya、Ashok Kanuka、Muralikrishna Valluri

  DOI：10.1016/j.tetlet.2022.154022

  日期：2022.8

  regio- and stereoselective palladium catalyzed electrocarboxylation of Baylis-Hillman acetates. We found an interesting unprecedented electrode material-controlled switchable regioselectivity. When Platinum was taken as cathode, benzylic carboxylation products were found to be the predominant regioisomers (condition A). Under similar reaction conditions when Nickel was taken as cathode, a complete reversal

  我们开发了一种新型的区域选择性和立体选择性钯催化 Baylis-Hillman 醋酸盐的电羧化反应。我们发现了一种有趣的、前所未有的电极材料控制的可切换区域选择性。当铂作为阴极时，发现苄基羧化产物是主要的区域异构体（条件 A）。在以镍为阴极的类似反应条件下，观察到区域选择性完全逆转，提供肉桂基羧化产物作为主要的区域异构体，仅具有 (E)-立体化学（条件 B）。我们提出了合理的机制来解释区域选择性的转换，这得到了 TEMPO 实验的进一步支持。
• RIZZACASA, MARK A.;SARGENT, MELVYN V., AUSTRAL. J. CHEM., 40,(1987) N 10, 1737-1743
  作者：RIZZACASA, MARK A.、SARGENT, MELVYN V.

  DOI：——

  日期：——
• Rizzacasa, Mark A.; Sargent, Melvyn V., Australian Journal of Chemistry, 1987, vol. 40, # 10, p. 1737 - 1743
  作者：Rizzacasa, Mark A.、Sargent, Melvyn V.

  DOI：——

  日期：——
• Synthetic Approach to Hypoxyxylerone, Novel Inhibitor of Topoisomerase I
  作者：Arnaud Piettre、Emmanuel Chevenier、Christine Massardier、Yves Gimbert、Andrew E. Greene

  DOI：10.1021/ol026454d

  日期：2002.9.1

  [GRAPHICS]A potential route to the topoisomerase I inhibitor hypoxyxylerone is demonstrated by a highly convergent synthesis of the penta(O-methyl) derivative. The key step in the approach is an anionic homo-Fries rearrangement, little used to date in natural product synthesis and employed here for the first time with a dinaphthalenic substrate, to access the pentacyclic system of hypoxyxylerone.