3,4-dimethoxypropynoic acid chloride | 816462-34-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-dimethoxypropynoic acid chloride
• 英文别名: 3,4-dimethoxyphenylpropioloyl chloride；3-(3,4-Dimethoxyphenyl)prop-2-ynoyl chloride
• CAS: 816462-34-7
• 化学式: C₁₁H₉ClO₃
• 分子量: 224.644
• InChiKey: WBPCKRDOOWQOHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxypropynoic acid chloride 在 Lindlar's catalyst 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成 1-(3-Methylbut-2-enyl)-3-(4-<(2Z)-3-(3',4'-dimethoxyphenyl)prop-2-enamido>butyl)urea
  参考文献：
  名称：

  Crombie, Leslie; Jarrett, Sandra R. M., Journal of the Chemical Society. Perkin transactions I, 1992, # 23, p. 3179 - 3184

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium 3,4-dimethoxyphenylpropiolate 在 氯化亚砜 作用下， 生成 3,4-dimethoxypropynoic acid chloride
  参考文献：
  名称：

  烷氧基取代芳基、芳炔基酮的合成和环化为金黄酮和黄酮

  摘要：

  1,3,5-三苄氧基苯与烷氧基取代的苯丙酰氯的酰化提供相应的芳基烷氧基芳基炔基酮，其中一个苄基已被除去。使用碱性试剂（丙酮中的碳酸钾最好）环化这些酚酮提供相应的 aurone 系统。当炔基酮的酚基被保护为叔丁基二甲基甲硅烷基醚，然后使用 18-crown-6 和氟化钾进行环化时，产生相应的黄酮和黄酮的混合物。酮类形成的副产物是相应的 β-氯查耳酮，它也可以在碱性条件下环化为 aurone 产物。相似地，

  DOI：

  10.1071/ch07348

文献信息

• A Gold(I)-Catalyzed Hydroamination/Cycloisomerization Cascade: Concise Synthesis of (±)-seco-Antofine and (±)-Septicine
  作者：Guilong Tian、Liangliang Song、Zhenghua Li、Koen Robeyns、Luc Van Meervelt、Erik V. Van der Eycken

  DOI：10.1021/acs.orglett.0c03062

  日期：2020.11.6

  procedure for the synthesis of highly functionalized N-heterocyclic 1,6-annulated 2-pyridones and 2,3-annulated 4-pyrimidinones has been elaborated through a gold-catalyzed tandem hydroamination/cycloisomerization cascade. This novel and highly efficient method allows the rapid construction of these diverse N-heterocyclic scaffolds starting from readily available building blocks, and shows a wide scope

  通过金催化串联加氢胺化/环异构化级联，详细阐述了合成高度官能化的 N-杂环 1,6-环 2-吡啶酮和 2,3-环 4-嘧啶酮的简洁而灵活的程序。这种新颖且高效的方法允许从现成的构建块开始快速构建这些不同的 N-杂环支架，并显示出广泛的范围和良好的官能团耐受性。(±)-seco-antofine 和 (±)-septine 的全合成是采用这种策略实现的。
• An Efficient Synthesis of Neoflavonoid Antioxidants Based on Montmorillonite K-10 Catalysis
  作者：Jian-Ming Lee、Tsui-Hwa Tseng、Yean-Jang Lee

  DOI：10.1055/s-2001-18436

  日期：——

  A new approach to synthesis of neoflavonoids, based on a high yielding Montmorillonite K-10 catalyzed lactone ring forming cyclization process, is described. The utility of this methodology is exemplified by its employment in the preparation of the substituted 4-phenylneoflavonoids 1-8. The free radical scavenging properties of these substances were evaluated. The neoflavonoids 1 and 5, which mimic esculetin-type antioxidants, were observed to quench hydrazyl free radicals.

  描述了一种基于高产量的蒙脱石K-10催化的内酯环形成环化过程的合成新黄酮类化合物的新方法。通过制备取代的4-苯基新黄酮1-8，展示了该方法的应用价值。评估了这些物质的自由基清除特性。观察到模拟七叶亭类抗氧化剂的新黄酮1和5能清除羟自由基。
• Studies on Disease-Modifying Antirheumatic Drugs. III. Bone Resorption Inhibitory Effects of Ethyl 4-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate (TAK-603) and Related Compounds.
  作者：Atsuo BABA、Tsuneo ODA、Shigehisa TAKETOMI、Kohei NOTOYA、Atsushi NISHIMURA、Haruhiko MAKINO、Takashi SOHDA

  DOI：10.1248/cpb.47.369

  日期：——

  In the course of our studies aimed at obtaining new drugs for treatment of bone and joint diseases, chemical modification of the potent bone resorption inhibitors justicidins, was performed and various naphthalene lactones, quinoline lactones and quinoline derivatives bearing an azole moiety at the side chain were prepared. Their inhibitory effects on bone resorption were evaluated by Raisz's method, and several compounds, including ethyl 4-(3, 4-dimethoxyphenyl)-6, 7-dimethoxy-2-(1, 2, 4-triazol-1-ylmethyl)quinoline-3-carboxylate (6c, TAK-603), were found to have activities comparable with or superior to the justicidins. The 4-(3-isopropoxy-4-methoxy)-phenyl derivative (6d), in particular, displayed a marked increase in potency. TAK-603 and compound 6d were very effective in preventing osteoclast formation and bone resorption by mature osteoclasts. Further, TAK-603 was shown to be effective in preventing bone loss in ovariectomized mice.

  我们的研究旨在获得治疗骨关节疾病的新药物，在研究过程中，我们对强效骨吸收抑制剂刚烷类化合物进行了化学修饰，制备出了各种萘内酯、喹啉内酯以及侧链含有唑基的喹啉衍生物。研究发现，包括 4-(3,4-二甲氧基苯基)-6,7-二甲氧基-2-(1,2,4-三唑-1-基甲基)喹啉-3-羧酸乙酯（6c，TAK-603）在内的几种化合物具有与刚烷类化合物相当或更高的活性。尤其是 4-（3-异丙氧基-4-甲氧基）-苯基衍生物（6d），其药效明显增强。TAK-603 和化合物 6d 在阻止破骨细胞形成和成熟破骨细胞的骨吸收方面非常有效。此外，TAK-603 还能有效防止卵巢切除小鼠的骨质流失。
• The intramolecular diels-alder reaction as a route to synthetic lignan lactones
  作者：L.H. Klemm、K.W. Gopinath、D. Hsu Lee、F.W. Kelly、E. Trod、T.M. McGuire

  DOI：10.1016/s0040-4020(01)82253-5

  日期：1966.1

  cyclized in refluxing acetic anhydride to form lignan lactones containing the 1-phenyl-naphthalene nucleus, as well as its 3,4-dihydro and 1,2,3,4-tetrahydro analogs, respectively. By this intramolecular Diels-Alder reaction the derived natural products dehydroanhydropicropodophyllin, dehydrodimethylconidendrin, rac-γ-apopicropodophyllin, and rac-isodesoxypicropodophyllin were readily synthesized. Although

  将苯基丙炔基苯基丙酸酯，反式肉桂酸苯基丙酸酯和反式肉桂酸顺式肉桂酸酯型的甲氧基和亚甲二氧基取代的不饱和开链酯在回流的乙酸酐中环化形成含1-苯基萘核的木脂素内酯。以及其3,4-二氢和1,2,3,4-四氢类似物。通过该分子内Diels-Alder反应的衍生的天然产物dehydroanhydropicropodophyllin，dehydrodimethylconidendrin，外消旋-γ-apopicropodophyllin，和外消旋-isodesoxypicropodophyllin被容易地合成。虽然反式-肉桂基部分在这些环化中仅充当二烯，苯基炔丙基可以充当“二烯”或亲二烯体。所形成的产品的结构是根据光谱特征和/或与真实样品的直接比较进行分配的。
• Synthesis and preliminary pharmacological evaluation of analogues of caracasanamide, a hypotensive natural product
  作者：Federico Corelli、Donata Dei、Giuliano Delle Monache、Bruno Botta、Carlo De Luca、Marco Carmignani、Anna Rita Volpe、Maurizio Botta

  DOI：10.1016/0960-894x(96)00079-0

  日期：1996.3

  Some analogues of the hypotensive agent caracasanamide have been synthesized and tested in vivo for cardiovascular effects. Derivative 2c emerged as the most interesting compound in the series. Structure-activity relationship is also discussed.