3-(p-methoxyphenyl)bicyclo<1.1.1>pentane-1-carboxylic acid | 156329-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(p-methoxyphenyl)bicyclo<1.1.1>pentane-1-carboxylic acid
• 英文别名: 3-(4-methoxyphenyl)bicyclo[1.1.1]pentane carboxylic acid；1-(4-methoxyphenyl)bicyclo[1.1.1]pentane-3-carboxylic acid；3-(4-methoxyphenyl)bicyclo[1.1.1]pentane-1-carboxylic acid
• CAS: 156329-83-8
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: FAVDDMXMFIJQSX-UHFFFAOYSA-N

物化性质

• 沸点：
  369.9±42.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(p-methoxyphenyl)bicyclo<1.1.1>pentane-1-carboxylic acid 在 氟烷 、 N,N'-二环己基碳二亚胺 作用下， 生成 1-bromo-3-(p-methoxyphenyl)bicyclo<1.1.1>pentane
  参考文献：
  名称：

  Synthesis of Some Bridgehead-Bridgehead-Disubstituted Bicyclo[1.1.1]pentanes

  摘要：

  The synthesis of a wide variety of 1,3-disubstituted bicyclo[1.1.1]pentanes is described, with particular emphasis on the generation of a series of S-X-substituted bicyclo[1.1.1]pentyl bromides required for solvolytic studies. Functional group manipulation at the bridgehead was readily accomplished in the majority of cases by radical processes in some instances, transformations were effected via carbanionic-type intermediates.

  DOI：

  10.1021/jo00090a015
• 作为产物：
  描述：

  1,3-二碘双环[1.1.1]戊烷 在 氢氧化钾 作用下， 以 苯 为溶剂， 反应 26.5h， 生成 3-(p-methoxyphenyl)bicyclo<1.1.1>pentane-1-carboxylic acid
  参考文献：
  名称：

  Formation and Reactions of Bicyclo[1.1.1]pentyl-1 Cations

  摘要：

  The ionization of l-bicyclo[1.1.1]pentyl halides was shown to initially form the 1,3-bridged bicycle[1.1.1]pentyl-l cation. It appears to be a transition state that leads to the bicyclo[1.1.0]butyl-1-carbinyl cation which can be trapped with azide ion and can be directly observed by NMR in SO2CIF. Although the major products of solvolysis of the halides are 3-methylenecyclobutyl derivatives, the corresponding cation was calculated to have a significantly higher energy than the bicyclobutylcarbinyl ion. Therefore, the products are probably formed by an attack of the nucleophile on the latter ion, accompanied by bond migration. The bridgehead iodide reacts under solvolytic conditions with azide ion to form bicyclo[1.1.0]butyl-l azide as a product. It also reacts with potassium hydroxide to give [1.1.1]propellane, and the same reaction occurs on dissolving in acetonitrile or pyridine. The reaction of 1,3-diiodobicyclo[1.1.1]pentane with ethoxide ion also was found to give [1.1.1]propellane via a nucleophilic attack on one of the iodines. The propellane reacts with methyl hypoiodite to give 3-iodobicyclo[1.1.1]pentyl-l cation, which can react with methanol to give 3-methoxybicyclo[1.1.1]pentyl-l iodide and with azide ion to give 3-iodobicyclo[1.1.1]pentyl-1 azide. These data provide evidence for a discrete 3-iodobicyclo[1.1.1]pentyl-l cation intermediate. The effect of substituents on the rate of solvolysis of bicyclo[1.1.1]pentyl-l iodide was studied. With 3-aryl substituents, a value of rho = -1.7 was found, which is similar to that observed in the solvolysis of 3-arylcyclobutyl tosylates (rho = -1.6). The 3-substituted bicyclopentyl halides usually form the corresponding 3-methylenecyclobutyl cations rather than bicyclo[1.1.0]butyl-1-carbinyl ions, because most substituents will help stabilize the former type of ion.

  DOI：

  10.1021/ja00105a046

文献信息

• N-Acylethanolamine Hydrolyzing Acid Amidase (NAAA) Inhibitors And Use Thereof
  申请人：Northeastern University

  公开号：US20190345132A1

  公开（公告）日：2019-11-14

  Disclosed herein are compounds represented by Structural Formula I: or a pharmaceutically acceptable salt thereof. Values for the variables in Structural Formula I are described herein. The compounds can be used to modulate (e.g., inhibit) N-acylethanolamine hydrolyzing acid amidase (NAAA) and thereby treat a variety of diseases, disorders and conditions mediated by NAAA, such as a gastrointestinal motility disorder, irritable bowel syndrome, an inflammatory bowel disorder, neuroinflammation, nicotine addiction, cancer, opioid dependence, analgesia, chemotherapy-induced neuropathic pain and pain. Also disclosed herein are compositions and methods including compounds of Structural Formula I, or a pharmaceutically acceptable salt thereof.

  本文披露了由结构式I表示的化合物：或其药学上可接受的盐。本文描述了结构式I中变量的值。这些化合物可用于调节（例如抑制）N-酰基乙醇胺水解酸酰胺酶（NAAA），从而治疗由NAAA介导的各种疾病、障碍和病症，例如胃肠运动障碍、肠易激综合征、炎症性肠病、神经炎症、尼古丁成瘾、癌症、阿片类药物依赖、止痛、化疗诱导的神经病理性疼痛和疼痛。本文还披露了包括结构式I中的化合物或其药学上可接受的盐的组合物和方法。
• N-acylethanolamine hydrolyzing acid amidase (NAAA) inhibitors and use thereof
  申请人：Northeastern University

  公开号：US10689357B2

  公开（公告）日：2020-06-23

  Disclosed herein are compounds represented by Structural Formula I: or a pharmaceutically acceptable salt thereof. Values for the variables in Structural Formula I are described herein. The compounds can be used to modulate (e.g., inhibit) N-acylethanolamine hydrolyzing acid amidase (NAAA) and thereby treat a variety of diseases, disorders and conditions mediated by NAAA, such as a gastrointestinal motility disorder, irritable bowel syndrome, an inflammatory bowel disorder, neuroinflammation, nicotine addiction, cancer, opioid dependence, analgesia, chemotherapy-induced neuropathic pain and pain. Also disclosed herein are compositions and methods including compounds of Structural Formula I, or a pharmaceutically acceptable salt thereof.

  本文公开了结构式 I 所代表的化合物： 或其药学上可接受的盐。结构式 I 中各变量的数值已在本文中描述。本发明化合物可用于调节（例如抑制）N-乙酰乙醇胺水解酸酰胺酶（NAAA），从而治疗由NAAA介导的各种疾病、失调和病症，如胃肠道运动障碍、肠易激综合征、炎症性肠病、神经炎症、尼古丁成瘾、癌症、阿片类药物依赖、镇痛、化疗诱导的神经性疼痛和疼痛。本文还公开了包括结构式 I 化合物或其药学上可接受的盐的组合物和方法。
• WO2021018857A5
  申请人：——

  公开号：WO2021018857A5

  公开（公告）日：2023-07-14
• [EN] N-ACYLETHANOLAMINE HYDROLYZING ACID AMIDASE (NAAA) INHIBITORS AND USE THEREOF<br/>[FR] INHIBITEURS DE NAAA - AMIDASE ACIDE D'HYDROLYSE DE LA N-ACYLÉTHANOLAMINE - ET LEUR UTILISATION
  申请人：UNIV NORTHEASTERN

  公开号：WO2019217977A1

  公开（公告）日：2019-11-14

  Disclosed herein are compounds represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof. Values for the variables in Structural Formula I are described herein. The compounds can be used to modulate (e.g, inhibit) N- acylethanolamine hydrolyzing acid amidase (NAAA) and thereby treat a variety of diseases, disorders and conditions mediated by NAAA, such as a gastrointestinal motility disorder, irritable bowel syndrome, an inflammatory bowel disorder, neuroinflammation, nicotine addiction, cancer, opioid dependence, analgesia, chemotherapy-induced neuropathic pain and pain. Also disclosed herein are compositions and methods including compounds of Structural Formula I, or a pharmaceutically acceptable salt thereof
• [EN] NOVEL COMPOUNDS MODULATING MIR-155<br/>[FR] NOUVEAUX COMPOSÉS MODULANT MIR-155
  申请人：[en]SAVERNA THERAPEUTICS AG

  公开号：WO2023152182A1

  公开（公告）日：2023-08-17

  Present invention relates to a compound according to formula (II): and all stereoisomers, racemic mixtures, tautomers, pharmaceutically acceptable salts, prodrugs, hydrates, solvates and polymorphs thereof, as well as pharmaceutical composition comprising instant compounds that can be used in treating and/or preventing and/or alleviating the symptoms of a disease characterized by the increased expression level of miR-155. Instant compounds are particularly useful in treating and/or preventing and/or alleviating the symptoms of systemic lupus erythematosus and scleroderma.