2-(o-tolyl)cyclopentanone | 52086-32-5

• 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: 2-(o-tolyl)cyclopentanone
• 英文别名: 2-(o-Tolyl)-cyclopentanon；2-(2-methylpheny)lcyclopentanone；2-(o-Tolyl)cyclopentan-1-one；2-(2-methylphenyl)cyclopentan-1-one
• CAS: 52086-32-5
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: LMFYCSUTNAAAQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(o-tolyl)cyclopentanone 在 4-二甲氨基吡啶 、 tetrakis(acetonitrile)copper(I) hexafluorophosphate 、 10-苯基-10H-吩噻嗪 、 盐酸羟胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 4,4'-二叔丁基-2,2'-二吡啶 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 为溶剂， 生成 2-(o-tolyl)hexanedinitrile
  参考文献：
  名称：

  双光氧化还原和铜催化的肟酯的对映选择性自由基开环氰化反应

  摘要：

  涉及高反应性自由基种类的催化对映选择性化学反应在很大程度上仍未开发。我们在此首次报道了通过双重光致氧化和铜催化的氧化还原活性肟酯的新型对映选择性自由基开环氰化反应。这种温和的方案显示出良好的官能团耐受性和广泛的底物范围，可生产出高收率和出色的对映选择性的多种旋光性烷基二腈，这是传统上难以获得的。

  DOI：

  10.1021/acs.orglett.9b03970
• 作为产物：
  描述：

  2-(2-Methylphenyl)cyclopentan-1-ol 在 aluminum oxide 、 pyridinium chlorochromate 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 2-(o-tolyl)cyclopentanone
  参考文献：
  名称：

  The identification of 7-[(R)-2-((1S,2S)-2-benzyloxycyclopentylamino)-1-hydroxyethyl]-4-hydroxybenzothiazolone as an inhaled long-acting β2-adrenoceptor agonist

  摘要：

  The optimisation of two series of 4-hydroxybenzothiazolone derived β2-adrenoceptor agonists, bearing α-substituted cyclopentyl and β-phenethyl amino-substituents, as inhaled long-acting bronchodilators is described. Analogues were selected for synthesis using a lipophilicity based hypothesis to achieve the targeted rapid onset of action in combination with a long duration of action. The profiling of the two series led to identification of the α-substituted cyclopentyl analogue 2 as the optimal compound with a comparable profile to the inhaled once-daily long-acting β2-adrenoceptor agonist indacaterol. On the basis of these data 2 was promoted as the backup development candidate to indacaterol from the Novartis LABA project.

  DOI：

  10.1016/j.bmcl.2014.06.014

文献信息

• Photoinduced C-C Bond Cleavage and Oxidation of Cycloketoxime Esters
  作者：Binlin Zhao、Hui Tan、Cheng Chen、Ning Jiao、Zhuangzhi Shi

  DOI：10.1002/cjoc.201800206

  日期：2018.11

  the traditional Beckmann rearrangement process has been established to build cyano‐containing ketones in the presence of photocatalyst. This novel transformation is remarkable with selective C—C bond cleavage and an oxidation process enabled by DMSO used as the solvent, oxidant, and oxygen source avoiding acid, base and toxic cyanide salts as the cyano source. Further applications in late‐stage modification

  已经建立了超越传统贝克曼重排过程的环酮肟酯的新型结构重组，以在光催化剂存在下构建含氰基的酮。这种新颖的转化过程具有显着的选择性CC键断裂和DMSO作为溶剂，氧化剂和氧源而避免了酸，碱和有毒氰化物盐作为氰基源的氧化过程。也已经报道了在复杂和手性分子的后期修饰中的进一步应用。
• Practical Direct α-Arylation of Cyclopentanones by Palladium/Enamine Cooperative Catalysis
  作者：Yan Xu、Tianshun Su、Zhongxing Huang、Guangbin Dong

  DOI：10.1002/anie.201510638

  日期：2016.2.12

  Direct arylation of cyclopentanones has been a long‐standing challenge because of competitive self‐aldol condensation and multiple arylations. Reported herein is a direct mono‐α‐C−H arylation of cyclopentanones with aryl bromides which is enabled by palladium/amine cooperative catalysis. This method is scalable and chemoselective with broad functional‐group tolerance. Application to controlled sequential

  由于竞争性的自我醛醇缩合和多种芳基化，环戊酮的直接芳基化一直是一个长期的挑战。本文报道的是环戊酮与芳基溴化物的直接单α-CH芳基化反应，这是通过钯/胺协同催化实现的。该方法具有可扩展性和化学选择性，并具有广泛的功能组耐受性。还证明了其在环戊酮的受控顺序芳基化中的应用。
• Highly Efficient and Enantioselective α-Arylation of Cycloalkanones by Scandium-Catalyzed Diazoalkane-Carbonyl Homologation
  作者：Jason Kingsbury、Victor Rendina、Hilan Kaplan

  DOI：10.1055/s-0031-1289650

  日期：2012.3

  Functionalized α-tertiary and -quaternary 2-arylcycloalkanones are rapidly accessed by scandium(III) triflate-catalyzed diazo­alkane-carbonyl homologations. Recent developments have allowed for carbon insertion reactions to be performed with catalyst loadings as low as 0.5 mol% on scales up to 5 mmol. Pairing readily available bis- and tris(oxazoline) based ligands with scandium triflate allows access to arylated medium ring carbocycles with enantioselectivities up to 98:2 er and >98% yield. The formal C-C insertion of aryldiazo­methanes into unsubstituted cycloalkanones provides a single-step solution to the ongoing challenge of α-arylation.

  功能化的α-叔和α-季2-芳基环烷酮通过三氟甲磺酸钪(III)催化的重氮甲烷-羰基同系化反应迅速获得。最近的进展使得碳插入反应能够在催化剂负载量低至0.5 mol%的情况下进行，规模可达5 mmol。结合易于获得的基于双和三噁唑啉的配体与三氟甲磺酸钪，可以合成具有高达98:2 对映体比和>98%产率的芳基化中环碳环。芳基重氮甲烷在无取代环烷酮中的正式C-C插入提供了一种一步解决α-芳基化持续挑战的方法。
• [EN] HYDROGENATION PROCESS<br/>[FR] PROCÉDÉ D'HYDROGÉNATION
  申请人：EXXONMOBIL CHEM PATENTS INC

  公开号：WO2011100013A1

  公开（公告）日：2011-08-18

  The present invention relates to a hydrogenation process that may be used in connection with the production of phenol. In the process, a composition comprising: (i) cyclohexylbenzene; and (ii) a hydrogenable component are contacted with hydrogen in the presence of a hydrogenation catalyst under hydrogenation conditions. The hydrogenable component can be one or more of an olefin, a ketone or phenol. The hydrogenation catalyst has hydrogenation component and a support.

  本发明涉及一种氢化工艺，可用于苯酚生产过程中。在该工艺中，将包括：（i）环己基苯；和（ii）可氢化组分的组合物在氢化催化剂的存在下，在氢化条件下与氢接触。可氢化组分可以是一个或多个烯烃，酮或苯酚。氢化催化剂具有氢化组分和支撑体。
• Hydrogenation Process
  申请人：Dakka Jihad M.

  公开号：US20120277472A1

  公开（公告）日：2012-11-01

  The present invention relates to a hydrogenation process that may be used in connection with the production of phenol. In the process, a composition comprising: (i) cyclohexylbenzene; and (ii) a hydrogenable component are contacted with hydrogen in the presence of a hydrogenation catalyst under hydrogenation conditions. The hydrogenable component can be one or more of an olefin, a ketone or phenol. The hydrogenation catalyst has hydrogenation component and a support.

  本发明涉及一种氢化过程，可以与苯酚生产相关联。在该过程中，将包括：(i) 环己基苯; 和(ii) 可氢化组分的组成物，在氢化催化剂的存在下，在氢化条件下与氢接触。可氢化组分可以是一种或多种烯烃、酮或苯酚。氢化催化剂具有氢化组分和支撑体。