diethyl 2-(2,4,6-trimethoxybenzylidene)malonate | 86726-44-5

• 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: diethyl 2-(2,4,6-trimethoxybenzylidene)malonate
• 英文别名: 1,3-Diethyl 2-[(2,4,6-trimethoxyphenyl)methylene]propanedioate；diethyl 2-[(2,4,6-trimethoxyphenyl)methylidene]propanedioate
• CAS: 86726-44-5
• 化学式: C₁₇H₂₂O₇
• 分子量: 338.357
• InChiKey: REEBLLANVJMSCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  diethyl 2-(2,4,6-trimethoxybenzylidene)malonate 以82%的产率得到
  参考文献：
  名称：

  SOHDA, TAKASHI;MIZUNO, KATSUTOSHI;HIRATA, TAKEO;MAKI, YOSHITAKA;KAWAMATSU+, CHEM. AND PHARM. BULL., 1983, 31, N 2, 560-569

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-三甲氧基苯甲醛 、 丙二酸二乙酯 以77%的产率得到
  参考文献：
  名称：

  SOHDA, TAKASHI;MIZUNO, KATSUTOSHI;HIRATA, TAKEO;MAKI, YOSHITAKA;KAWAMATSU+, CHEM. AND PHARM. BULL., 1983, 31, N 2, 560-569

  摘要：

  DOI：

文献信息

• Antiulcer activity of 5-benzylthiazolidine-2,4-dione derivatives.
  作者：TAKASHI SOHDA、KATSUTOSHI MIZUNO、TAKEO HIRATA、YOSHITAKA MAKI、YUTAKA KAWAMATSU

  DOI：10.1248/cpb.31.560

  日期：——

  5-Benzylthiazolidine-2, 4-dione derivatives were prepared and examined for antisecretory and antiulcer activities using pylorus-ligated rats and water-immersion stress rats. Some of these compounds, in particular, 5-(2, 4, 5-tripropoxybenzyl) thiazolidine-2, 4-dione (4) and 5-(2, 4-dimethoxybenzyl) thiazolidine-2, 4-dione (23), exhibited pronounced pharmacological activities. Structure-activity relationships are discussed.

  制备了5-苄基-噻唑烷-2,4-二酮衍生物，并通过结扎大鼠幽门和水浸应激大鼠模型进行了抗分泌和抗溃疡活性的检验。其中一些化合物，尤其是5-(2, 4, 5-三丙氧基苄基)噻唑烷-2, 4-二酮（4）和5-(2, 4-二甲氧基苄基)噻唑烷-2, 4-二酮（23），表现出显著的药理活性。结构-活性关系在此进行了讨论。
• Lewis Acid-Catalyzed [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes and Enamines: Enantioselective Synthesis of Nitrogen-Functionalized Cyclopentane Derivatives
  作者：Kamal Verma、Prabal Banerjee

  DOI：10.1002/adsc.201600221

  日期：2016.6.30

  efficient method for the synthesis of nitrogen‐functionalized cyclopentane derivatives via [3+2] cycloaddition of enamines with donor‐acceptor cyclopropanes in the presence of catalytic amounts of various Lewis acids at room temperature has been developed; furthermore, the corresponding β‐amino acid was synthesized by monodecarboxylation and hydrogenolysis. An enantioenriched synthesis of nitrogen‐functionalized

  在室温下催化量的各种路易斯酸存在下，开发了一种简单有效的方法，可通过烯胺与供体-受体环丙烷的[3 + 2]环加成反应，合成氮官能化的环戊烷衍生物；此外，通过单脱羧和氢解合成了相应的β-氨基酸。通过外消旋给体-受体环丙烷的动态动力学不对称转化，对氮官能化的环戊烷衍生物进行了对映体富集合成，采用铜络合物[Cu（OTf）2 - L1 ]作为催化剂，对映体比例高达8：1。
• Substituent and Lewis Acid Promoted Dual Behavior of Epoxides towards [3+2]-Annulation Reactions with Donor-Acceptor Cyclopropanes: Synthesis of Substituted Cyclopentane and Tetrahydrofuran
  作者：Ashok Kumar Pandey、Rohit Kumar Varshnaya、Prabal Banerjee

  DOI：10.1002/ejoc.201601549

  日期：2017.3.27

  substituents present in both reacting partners produced different products. The C-attack gave functionalized cyclopentane derivatives while the O-attack furnished tetrahydrofuran derivatives via [3+2]-annulation reactions. Moreover, to increase the utility of our method, synthesized diasteriomeric cyclopentane derivatives were converted into synthetically useful cyclopentene and cyclopentanone analog.

  取代基和路易斯酸促进从环氧化物生成官能化烯醇化物。烯醇化物对供体-受体环丙烷的不同攻击，即 C-攻击或 O-攻击，取决于两个反应伙伴中存在的取代基，产生不同的产物。C-攻击产生官能化的环戊烷衍生物，而O-攻击通过[3+2]-环化反应提供四氢呋喃衍生物。此外，为了提高我们方法的实用性，合成的非对映环戊烷衍生物被转化为合成有用的环戊烯和环戊酮类似物。
• Lewis Acid-Catalyzed Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates: A New Efficient Route to 2-Styrylmalonates
  作者：Alexey O. Chagarovskiy、Olga A. Ivanova、Eduard R. Rakhmankulov、Ekaterina M. Budynina、Igor V. Trushkov、Mikhail Ya. Melnikov

  DOI：10.1002/adsc.201000636

  日期：2010.12.17

  A facile efficient approach to the 2-styrylmalonates via the Lewis acid-catalyzed isomerization of 2-arylcyclopropane-1,1-dicarboxylates has been developed. The efficiency of this method was demonstrated for a representative series of such cyclopropanes. The isomerization proceeds chemo-, regio- and stereoselectively to afford E-styrylmalonates in good yields.

  已经开发了通过路易斯酸催化的2-芳基环丙烷-1，1-二羧酸酯异构化2-苯乙烯基丙二酸酯的简便有效方法。对于代表性的此类环丙烷系列，证明了该方法的效率。异构化进行化学，区域和立体选择性，以高收率得到E-苯乙烯基丙二酸酯。
• Lewis Acid Catalyzed Formal [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes and 1-Azadienes: Synthesis of Imine Functionalized Cyclopentanes and Pyrrolidine Derivatives
  作者：Kamal Verma、Prabal Banerjee

  DOI：10.1002/adsc.201700744

  日期：2017.11.10

  Lewis acid catalyzed formal [3+2] cycloadditions of 1-azadienes with donor acceptor cyclopropanes to synthesize varieties of imine functionalized cyclopentanes and pyrrolidine derivatives in moderate to high yield have been developed. Moreover, pharmaceutically relevant azabicyclo[3.2.1]octane, bearing two all-carbon quaternary stereogenic centers at the bridgehead positions, has been synthesized by

  路易斯酸催化了1-氮二烯与供体受体环丙烷的正式[3 + 2]环加成反应，以中等至高收率合成了亚胺官能化的环戊烷和吡咯烷衍生物。此外，已经通过鼻基基团脱保护和亚胺官能化的环戊烷衍生物的分子内酰胺化合成了药学上相关的氮杂双环[3.2.1]辛烷，其在桥头位置具有两个全碳季立体中心。