methyl 5-methoxy-2,3-dihydro-1-benzofuran-2-carboxylate | 653578-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: methyl 5-methoxy-2,3-dihydro-1-benzofuran-2-carboxylate
• CAS: 653578-12-2
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: RIGSSTWBPMWYRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-methoxy-2,3-dihydro-1-benzofuran-2-carboxylate 在 六甲基磷酰三胺 、 三溴化硼 、 caesium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.25h， 生成 5-{3-[2-Chloro-4-(2,2,2-trifluoro-ethoxy)-phenoxy]-propoxy}-2-methyl-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Novel 2,3-Dihydrobenzofuran-2-carboxylic Acids:  Highly Potent and Subtype-Selective PPARα Agonists with Potent Hypolipidemic Activity

  摘要：

  The design and synthesis of a novel class of 2,3-dihydrobenzofuran-2-carboxylic acids as highly potent and subtype-selective PPAR alpha agonists are reported. Systematic study of structure-activity relationships has identified several key structural elements within this class for maintaining the potency and subtype selectivity. Select compounds were evaluated in animal models of dyslipidemia using Syrian hamsters and male Beagle dogs, and all these compounds displayed excellent cholesterol- and triglyceride-lowering activity at dose levels that were much lower than the marketed weak PPAR alpha agonist fenofibrate.

  DOI：

  10.1021/jm050373g
• 作为产物：
  描述：

  5-甲氧基-1-苯并呋喃-2-甲酸甲酯 在 钯 氢气 、 silica gel 、 正己烷 、 乙酸乙酯 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以ethyl acetate to give 1.3 g 5-methoxy-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester的产率得到methyl 5-methoxy-2,3-dihydro-1-benzofuran-2-carboxylate
  参考文献：
  名称：

  PPAR alpha selective compounds for the treatment of dyslipidemia and other lipid disorders

  摘要：

  一类苯并二氢呋喃化合物，其结构式（I）如下，以及其药学上可接受的盐，可用作治疗化合物，特别是用于治疗高脂血症、高胆固醇血症、脂质代谢异常和其他脂质紊乱，并延缓或降低与这些疾病相关的疾病和后遗症的发生风险，如动脉粥样硬化。

  公开号：

  US07524882B2

文献信息

• Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands: Design, Synthesis, and Use in Cu-Catalyzed Inter- and Intramolecular Asymmetric O–H Insertion Reactions
  作者：Shinji Kitagaki、Shunsuke Murata、Kisaki Asaoka、Kenta Sugisaka、Chisato Mukai、Naoko Takenaga、Keisuke Yoshida

  DOI：10.1248/cpb.c18-00519

  日期：2018.10.1

  insertion reactions of α-diazo esters. The reactivities and enantioselectivities of Cu complexes of the synthesized bisoxazoline ligands were lower than those of ligands without central chirality. However, planar chiral [2.2]paracyclophane-based bisoxazoline ligands with an inserted benzene spacer that had a sterically demanding isopropyl substituent showed good enantioselectivities in inter- and intramolecular

  合成了直接连接到平面手性[2.2]对环环烷骨架上的中心手性双恶唑啉，并在Cu催化的α-重氮酯的分子间乙醇氢插入反应中将其作为不对称配体进行了评估。合成的双恶唑啉配体的Cu配合物的反应性和对映选择性低于没有中心手性的配体。然而，具有手性要求高的异丙基取代基的带有插入的苯间隔基的平面手性[2.2]对环环烷基双恶唑啉配体在分子间和分子内芳族OH插入反应中没有良好的对映选择性，而没有中心手性。
• Ppar alpha selective compounds for the treatment of dyslipidemia and other lipid disorders
  申请人：Shi Q. Guo

  公开号：US20050228044A1

  公开（公告）日：2005-10-13

  A class of benzodihydrofuran compounds having the structure of formula (I) below and pharmaceutically acceptable salts thereof are useful as therapeutic compounds, particularly in the treatment of hyperlipidemia, hypercholesterolemia, dyslipidemia, and other lipid disorders, and in delaying the onset of or reducing the risk of conditions and sequelae that are associated with these diseases, such as atherosclerosis.

  一类苯并二氢呋喃化合物，其结构式为（I），以及其药学上可接受的盐，可用作治疗化合物，特别是用于治疗高脂血症、高胆固醇血症、脂质代谢异常和其他脂质紊乱，并延缓或降低与这些疾病相关的病症和后遗症的发生风险，如动脉粥样硬化。
• PPAR alpha selective compounds for the treatment of dyslipidemia and other lipid disorders
  申请人：Merck & Co., Inc.

  公开号：US07524882B2

  公开（公告）日：2009-04-28

  A class of benzodihydrofuran compounds having the structure of formula (I) below and pharmaceutically acceptable salts thereof are useful as therapeutic compounds, particularly in the treatment of hyperlipidemia, hypercholesterolemia, dyslipidemia, and other lipid disorders, and in delaying the onset of or reducing the risk of conditions and sequelae that are associated with these diseases, such as atherosclerosis.

  一类苯并二氢呋喃化合物，其结构式（I）如下，以及其药学上可接受的盐，可用作治疗化合物，特别是用于治疗高脂血症、高胆固醇血症、脂质代谢异常和其他脂质紊乱，并延缓或降低与这些疾病相关的疾病和后遗症的发生风险，如动脉粥样硬化。
• Photoredox/HAT-Catalyzed Dearomative Nucleophilic Addition of the CO₂ Radical Anion to (Hetero)Aromatics
  作者：Saeesh R. Mangaonkar、Hiroki Hayashi、Hideaki Takano、Wataru Kanna、Satoshi Maeda、Tsuyoshi Mita

  DOI：10.1021/acscatal.2c06192

  日期：2023.2.17

  exhibits high reactivity in single-electron reduction reactions due to the concomitant release of stable CO2, or Giese-type reactions, especially for electron-deficient alkenes and styrene derivatives. In contrast to previous reports, we herein disclose the development of a robust method for the introduction of CO2•–, which can be generated from cesium formate under photoredox/hydrogen atom transfer (HAT)

  CO 2的自由基阴离子(CO 2 •– ) 是一种强亲核自由基，在现代有机化学中应用迅速。由于伴随释放稳定的 CO 2或 Giese 型反应，这种自由基物种在单电子还原反应中表现出高反应性，尤其是对于缺电子烯烃和苯乙烯衍生物。与之前的报告相比，我们在此披露了引入 CO 2的稳健方法的开发•–，可在光氧化还原/氢原子转移 (HAT) 催化下由甲酸铯生成，转化为稳定的杂芳烃，如苯并呋喃、苯并噻吩和吲哚衍生物，以提供合成有用的 α-氧、α-硫代和 α-氨基酸衍生物中高产。此外，当使用缺电子萘衍生物时，单电子还原和Giese型亲核加成同时发生，可以高产率地制备羧化四氢萘衍生物。此外，一种带有氰基的四氢萘通过氢化和环化还原氰基官能团，转化为相应的γ-丁内酰胺。据我们所知，
• Spirolactams as inhibitors of ROCK
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US10696674B2

  公开（公告）日：2020-06-30

  The present invention provides compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective ROCK inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating cardiovascular, smooth muscle, oncologic, neuropathologic, autoimmune, fibrotic, and/or inflammatory disorders using the same.

  本发明提供了式(I)化合物：或其立体异构体、同系物或药学上可接受的盐，其中所有变量如本文所定义。这些化合物是选择性 ROCK 抑制剂。本发明还涉及包含这些化合物的药物组合物以及使用这些化合物治疗心血管、平滑肌、肿瘤、神经病理、自身免疫、纤维化和/或炎症性疾病的方法。