5-[1-(3-hydroxy-4-methoxyphenyl)-ethylidene]2,2-dimethyl[1,3]dioxane-4,6-dione | 847259-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-[1-(3-hydroxy-4-methoxyphenyl)-ethylidene]2,2-dimethyl[1,3]dioxane-4,6-dione
• 英文别名: 5-(3-hydroxy-4-methoxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione；5-(3-hydroxy-4-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione；5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 847259-17-0
• 化学式: C₁₄H₁₄O₆
• 分子量: 278.262
• InChiKey: MKYHYIPISWTZBP-UHFFFAOYSA-N

物化性质

• 熔点：
  130-131 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  579.9±50.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• 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：

  5-[1-(3-hydroxy-4-methoxyphenyl)-ethylidene]2,2-dimethyl[1,3]dioxane-4,6-dione 在 盐酸 、 氯化亚砜 、 三丁基膦 、 水 、 sodium hydroxide 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 35.25h， 生成 3-cyclopropyl-3-(3-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-4-methoxyphenyl)propanoic acid
  参考文献：
  名称：

  EP2816032

  摘要：

  公开号：
• 作为产物：
  描述：

  异香兰素 、 丙二酸环(亚)异丙酯 在 溴化氰 、 sodium ethanolate 作用下， 以70%的产率得到5-[1-(3-hydroxy-4-methoxyphenyl)-ethylidene]2,2-dimethyl[1,3]dioxane-4,6-dione
  参考文献：
  名称：

  球磨制酸合成双螺环丙烷

  摘要：

  在溴化氰和乙醇钠（EtONa）存在下，2,2-二甲基-1,3-二恶烷-4,6-二酮（麦德鲁姆酸）与各种固体醛的反应导致选择性和有效地形成双-基于Meldrum酸的螺环丙烷，温度范围为0°C至室温。获得的产物具有良好至优异的产率。通过1 H NMR，13 C NMR，FT-IR光谱，质量分析和X射线晶体学技术进行结构阐明。还讨论了在无溶剂条件下形成产品的可能机理。

  DOI：

  10.1002/jccs.201400320

文献信息

• Synthesis and HIV-1 integrase inhibitory activity of spiroundecane(ene) derivatives
  作者：Elvira E. Shults、Elena A. Semenova、Allison A. Johnson、Svetlana P. Bondarenko、Irina Y. Bagryanskaya、Yuri V. Gatilov、Genrikh A. Tolstikov、Yves Pommier

  DOI：10.1016/j.bmcl.2006.11.094

  日期：2007.3

  preferred for IN inhibition. Moreover, crosslinking experiments showed that spiroundecane derivatives did not affect IN-DNA binding at concentrations that block IN catalytic activity, indicating spiroundecane derivatives inhibit preformed IN-DNA complex. The moderate toxicity of spiroundecane(ene) derivatives encourages the further design of therapeutically relevant analogues based on this novel chemotype

  使用Diels-Alder反应合成了15种2,4-二氧杂螺环[5.5]十一烷酮和2,4-二氧杂螺环[5.5]十一烷-8-烯（螺环十一烷（烯））衍生物。检查了对人免疫缺陷病毒整合酶（IN）的抑制作用。八种螺环十一烷（ene）衍生物可抑制IN催化的3'加工和链转移反应。SAR研究表明，具有至少一个呋喃部分的十一烷核心优选用于IN抑制。此外，交联实验表明，螺环烷衍生物在影响IN催化活性的浓度下不影响IN-DNA结合，表明螺环烷衍生物抑制了预先形成的IN-DNA复合物。螺环十一烷（ene）衍生物的中等毒性鼓励基于这种新型IN抑制剂化学型的治疗相关类似物的进一步设计。
• AROMATIC RING COMPOUND
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US20150045378A1

  公开（公告）日：2015-02-12

  Provided is an aromatic ring compound having a GPR40 agonist activity. A compound represented by the formula (I): wherein each symbol is as described in the DESCRIPTION, or a salt thereof has a GPR40 agonist activity, and is useful as an agent for the prophylaxis or treatment of diabetes and the like.

  提供了一种具有GPR40激动剂活性的芳香环化合物。式（I）所表示的化合物：其中每个符号如说明中所述，或其盐具有GPR40激动剂活性，并且可用作预防或治疗糖尿病等疾病的药剂。
• Aromatic ring compound
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US09181186B2

  公开（公告）日：2015-11-10

  Provided is an aromatic ring compound having a GPR40 agonist activity. A compound represented by the formula (I): wherein each symbol is as described in the DESCRIPTION, or a salt thereof has a GPR40 agonist activity, and is useful as an agent for the prophylaxis or treatment of diabetes and the like.

  提供了一种具有GPR40激动剂活性的芳香环化合物。式（I）所表示的化合物：其中每个符号如描述中所述，或其盐具有GPR40激动剂活性，并且可用作预防或治疗糖尿病等疾病的药剂。
• Synthesis and biological evaluation of arylidene analogues of Meldrum’s acid as a new class of antimalarial and antioxidant agents
  作者：Harmeet S. Sandhu、Sameer Sapra、Mukesh Gupta、Kunal Nepali、Raju Gautam、Sunil Yadav、Raj Kumar、Sanjay M. Jachak、Manoj Chugh、Manish K. Gupta、Om P. Suri、K.L. Dhar

  DOI：10.1016/j.bmc.2010.06.033

  日期：2010.8

  A series of arylidene analogues of Meldrum's acid were synthesized and evaluated for in vitro antimalarial and antioxidant activities for the first time. The influence of various physico-chemical parameters such as dielectric constant (epsilon), donor number (DN), acceptor number (AN), hydrogen bond donor (HBD), hydrogen bond acceptor (HBA), and solubilizing power of the solvents on Meldrum's acid anion generation and thus on promoting the Knoevenagel condensation of Meldrum's acid with aryl aldehydes has been discussed. Five compounds 9l, 9m, 9n, 9r, and 9s were found to be most active against Plasmodium falciparum with IC(50) values in the range of 9.68-16.11 mu M. Compound 9l exhibited the most potent antimalarial activity (IC(50) 9.68 mu M). The compounds were also found to possess antioxidant activity when tested against DPPH and ABTS free radicals. (C) 2010 Elsevier Ltd. All rights reserved.
• Diels–Alder Reactions with Cyclic Sulfones: VII. Synthesis of 1-Benzothiophene 1,1-Dioxide Derivatives
  作者：G. N. Andreev、E. E. Shul’ts、A. A. Volkov、M. M. Shakirov、I. Yu. Bagryanskaya、Yu. V. Gatilov、G. A. Tolstikov

  DOI：10.1023/b:rujo.0000044549.81561.4f

  日期：2004.6

  5-Arylmethylene-2,2-dimethyl-1,3-dioxane-4,6-diones reacted with 5-isopropenyl-2,3-dihydrothiophene 1,1-dioxide to give the corresponding ortho-addition products, 5-aryl-2',2',7-trimethyl-3,3a,5,6-tetrahydro-2H-spiro[1-benzothiophene-4,5'-[1,3]dioxane]-4',6'-dione 1,1-dioxides. Their aminolysis resulted in opening of the 1,3-dioxane ring and formation of 4-carbamoyl-7-methyl-2,3,3a,4,5,6-hexahydro-l-benzothiophene-4-carboxylic acid 1,1-dioxide whose structure was determined by X-ray analysis. Reactions of the spiro adducts with amines and hydrazine hydrate afforded the corresponding mono- or dicarboxylic acid monoamides (hydrazide).