2-(Cyclopentanecarbonyl)benzoic acid | 143915-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(Cyclopentanecarbonyl)benzoic acid
• CAS: 143915-56-4
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: LMYXXIJKSAKDOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(Cyclopentanecarbonyl)benzoic acid 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 4-Cyclopentyl-2-(2-imidazol-1-ylethyl)phthalazin-1-one
  参考文献：
  名称：

  Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-Imidazolyl)alkyl]-1(2H)-phthalazinones

  摘要：

  A number of 4-substituted 2-[omega-(1-imidazolyl)allryl]-1(2H)-phthalazinones were synthesized in order to develop agents possessing both thromboxane Az synthetase inhibitory and bronchodilatory activities. The pharmacological evaluation of these compounds disclosed that they have both activities to various extents. Both activities were slightly dependent on the length of the 2-substituents and largely affected by the nature of the 4-substituents. Compounds bearing phenyl and thienyl groups exhibited relatively high and well-rounded activities. Among these compounds, 12j and 15f were found to be the most effective agents having well-rounded activities in vitro and in vivo. Introduction of a carboxyl group reduced both activities contrary to our expectation. 4-(3-Pyridyl)phthalazinone 18b was of particular interest because of unexpectedly high in vivo activities in spite of an absence of significant in vitro activities.

  DOI：

  10.1021/jm00077a008
• 作为产物：
  描述：

  苯酐 、 Cyclopentylmagnesium chloride 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 2-(Cyclopentanecarbonyl)benzoic acid
  参考文献：
  名称：

  Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-Imidazolyl)alkyl]-1(2H)-phthalazinones

  摘要：

  A number of 4-substituted 2-[omega-(1-imidazolyl)allryl]-1(2H)-phthalazinones were synthesized in order to develop agents possessing both thromboxane Az synthetase inhibitory and bronchodilatory activities. The pharmacological evaluation of these compounds disclosed that they have both activities to various extents. Both activities were slightly dependent on the length of the 2-substituents and largely affected by the nature of the 4-substituents. Compounds bearing phenyl and thienyl groups exhibited relatively high and well-rounded activities. Among these compounds, 12j and 15f were found to be the most effective agents having well-rounded activities in vitro and in vivo. Introduction of a carboxyl group reduced both activities contrary to our expectation. 4-(3-Pyridyl)phthalazinone 18b was of particular interest because of unexpectedly high in vivo activities in spite of an absence of significant in vitro activities.

  DOI：

  10.1021/jm00077a008

文献信息

• An Asymmetric Aerobic Aza-Wacker-Type Cyclization: Synthesis of Isoindolinones Bearing Tetrasubstituted Carbon Stereocenters
  作者：Guoqiang Yang、Chaoren Shen、Wanbin Zhang

  DOI：10.1002/anie.201203693

  日期：2012.9.3

  It's all in the solvent: An enantioselective variant of an aza‐Wacker‐type cyclization that gives isoindolinones containing tetrasubstituted carbon centers α to the nitrogen atom has been developed (see scheme; tfa=trifluoroacetate). The use of a highly coordinating solvent is crucial for the activity of the catalyst and the stereoselectivity the reaction (up to 99 % ee).

  一切都在溶剂中：已经开发出aza-Wacker型环化的对映体选择性变体，该变体可将含四取代碳中心α的异吲哚啉酮带至氮原子（参见方案； tfa =三氟乙酸盐）。使用高度配位的溶剂对于催化剂的活性和反应的立体选择性（至多99％ee）至关重要 。
• Palladium-Catalyzed Aerobic Aminooxygenation of Alkenes for Preparation of Isoindolinones
  作者：Xuezhen Kou、Yu Li、Liang Wu、Xinghua Zhang、Guoqiang Yang、Wanbin Zhang

  DOI：10.1021/acs.orglett.5b02703

  日期：2015.11.20

  A palladium-catalyzed intramolecular isoindolinone-forming aminooxygenation of alkenes with 1 atm of oxygen as oxidant is reported. A variety of functionalized alkenes and carboxylic acids can be used, and high yields were observed. Preliminary mechanistic studies revealed that the aminooxygenation products were formed through the oxidation of a C–PdII species using a strong oxidant, peroxide, which

  报道了钯催化分子内异吲哚满酮形成的氨基氧合反应，其中氧原子为1个大气压。可以使用多种官能化的烯烃和羧酸，并且观察到高收率。初步的机理研究表明，氨基氧化产物是通过使用强氧化剂过氧化物将C-Pd II物种氧化而形成的，该过氧化物是由Pd（OAc）2 / bpy / O 2 / HOAc催化系统原位产生的。
• Enantioselective Palladium(II)-Catalyzed Intramolecular Aminoarylation of Alkenes by Dual N−H and Aryl C−H Bond Cleavage
  作者：Wen Zhang、Pinhong Chen、Guosheng Liu

  DOI：10.1002/anie.201700889

  日期：2017.5.2

  An asymmetric palladium‐catalyzed intramolecular oxidative aminoarylation of alkenes has been developed with quinoline–oxazoline chiral ligands and Ag2CO3 as the oxidant. Various indolines containing a quaternary stereogenic center were synthesized in high yield with excellent enantioselectivity. Preliminary mechanistic studies suggest that the addition of a catalytic amount of phenylglyoxylic acid

  用喹啉-恶唑啉手性配体和Ag 2 CO 3作为氧化剂，开发了不对称钯催化的烯烃分子内氧化氨基芳基化反应。含有四元立体异构中心的各种二氢吲哚以高产率合成，具有出色的对映选择性。初步的机理研究表明，加入催化量的苯乙醛酸可显着加快反应速度，并略微提高对映选择性。
• [EN] KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE
  申请人：DEVGEN NV

  公开号：WO2005082367A1

  公开（公告）日：2005-09-09

  The invention provides the use of a compound or a composition comprising said compound for inhibiting the activity of at least one kinase, other than ROCK kinase, in vitro or in vivo, pharmaceutical and/or veterinary compositions comprising such compounds, medical and veterinary uses of such compounds and the compounds themselves.

  该发明提供了一种化合物或含有该化合物的组合物用于抑制体外或体内至少一种激酶（除ROCK激酶外）的活性，包括这些化合物的药用和/或兽医学组合物，这些化合物的医药和兽医用途以及化合物本身。
• Pd^II -Catalyzed Oxidative Tandem aza-Wacker/Heck Cyclization for the Construction of Fused 5,6-Bicyclic N,O-Heterocycles
  作者：Chenghao Ye、Xuezhen Kou、Jingzhao Xia、Guoqiang Yang、Li Kong、Quhao Wei、Wanbin Zhang

  DOI：10.1002/asia.201800646

  日期：2018.8.6

  A PdII‐catalyzed oxidative tandem cyclization was developed for the construction of fused 5,6‐bicyclic N, O‐heterocycles. This reaction was enabled by the combined use of a 3‐methylpyridine ligand and pentafluorobenzoic acid additive. A range of heterocyclic products with different substituents could be prepared in moderate to good yields via this methodology. Several transformations, including a scaled‐up

  Pd II催化的氧化串联环化反应被开发用于构建稠合的5,6-双环N，O-杂环。通过联合使用3-甲基吡啶配体和五氟苯甲酸添加剂可以实现该反应。通过该方法，可以以中等到良好的产率制备一系列具有不同取代基的杂环产物。一些变革，包括产品的扩大规模的准备 2，也分别进行了展示我们的方法的良好的适用性。