2-(2-bromophenyl)cyclopentanone | 847355-79-7

• 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: 2-(2-bromophenyl)cyclopentanone
• 英文别名: 2-(2-bromophenyl)cyclopentan-1-one；2-(2-Bromophenyl)cyclopentan-1-one
• CAS: 847355-79-7
• 化学式: C₁₁H₁₁BrO
• 分子量: 239.112
• InChiKey: AMHWCWQNINRFGX-UHFFFAOYSA-N

物化性质

• 沸点：
  311.0±42.0 °C(Predicted)
• 密度：
  1.444±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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-(2-bromophenyl)cyclopentanone 在 tris(dibenzylideneacetone)dipalladium (0) 、 双(2-二苯基磷苯基)醚 diphosphorus pentasulfide 、 六甲基二硅氧烷 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 41.0h， 生成 2,3-dihydro-1H-benzo[b]cyclopenta[d]thiophene
  参考文献：
  名称：

  Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes

  摘要：

  Enolates derived from alpha-(ortho-haloaryl)-substituted ketones undergo palladium-catalysed C-O bond formation to deliver benzofuran products in good yield. A catalyst generated from Pd-2(dba)(3) and the ligand DPEphos effects the key bond formation to deliver a variety of substituted products from both cyclic and acyclic precursors. The analogous thio-ketones undergo C-S bond formation using identical reaction conditions and are converted to benzothiophene products. A cascade sequence that produces the required a-aryl ketones in situ has also been developed, although the substrate scope is more restricted. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.004
• 作为产物：
  描述：

  邻溴苯甲醛 在 potassium tert-butylate 、 间氯过氧苯甲酸 、 lithium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 42.5h， 生成 2-(2-bromophenyl)cyclopentanone
  参考文献：
  名称：

  钯催化的 α-(2-溴芳基) 酮的硼化环化形成 1,2-苯并氧杂环硼烷

  摘要：

  在此，我们报道了钯催化 α-(2-溴芳基) 酮的硼化环化以提供 1,2-苯并氧杂环胺。所开发的体系与多种官能团（Me、t -Bu、OMe、NMe 2、F、Cl、CN、CF 3、CO 2 Me 和杂芳基）兼容，适用于 B-O- 的合成。含有三环和四环稠环化合物。

  DOI：

  10.1021/acs.orglett.2c03033

文献信息

• 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。
• Palladium-catalyzed aryl halide carbonylation–intramolecular O-enolate acylation: efficient isocoumarin synthesis, including the synthesis of thunberginol A
  作者：Andrew C. Tadd、Mark R. Fielding、Michael C. Willis

  DOI：10.1039/b917839b

  日期：——

  Exposure of a series of α-(o-haloaryl)-substituted ketones to palladium-catalyzed carbonylation conditions leads to the formation of the corresponding isocoumarins. Balloon pressure of CO is sufficient to achieve high yielding reactions, and both cyclic and acyclic ketones are efficient substrates. The utility of the method is illustrated by a short synthesis of the natural product thunberginol A.

  一系列α-(o-卤芳基)-取代酮在钯催化的羰基化条件下处理，导致相应异香豆素的形成。使用气球压力的CO即可实现高产率反应，且环状和非环状酮都是高效底物。这种方法的实用性通过简短合成天然产物thunberginol A得到了说明。
• Multicomponent Assembly of Highly Substituted Indoles by Dual Palladium-Catalyzed Coupling Reactions
  作者：John M. Knapp、Jie S. Zhu、Dean J. Tantillo、Mark J. Kurth

  DOI：10.1002/anie.201204633

  日期：2012.10.15

  Highly substituted indoles were synthesized by a palladium‐catalyzed reaction involving three independent components in a one‐pot reaction. Two distinct palladium‐catalyzed coupling reactions occur with a single catalytic system: a Buchwald‐Hartwig reaction and an arene‐alkene coupling. Quantum chemical computations provide insight into the mechanism of the latter coupling step.

  高度取代的吲哚是通过钯催化的反应合成的，该反应涉及一锅反应中的三个独立组分。两个不同的钯催化偶联反应发生在单一催化体系中：Buchwald-Hartwig 反应和芳烃-烯烃偶联反应。量子化学计算提供了对后面耦合步骤机制的深入了解。
• Catalytic Diazoalkane-Carbonyl Homologation: Synthesis of 2,2-Diphenylcycloheptanone and Other Quaternary or Tertiary Arylalkanones and Spirocycles by Ring Expansion
  作者：Jason S. Kingsbury

  DOI：10.15227/orgsyn.098.0343

  日期：——
• Palladium-Catalyzed Tandem Alkenyl and Aryl C?N Bond Formation: A Cascade N-Annulation Route to 1-Functionalized Indoles
  作者：Michael C. Willis、Gareth N. Brace、Ian P. Holmes

  DOI：10.1002/anie.200461598

  日期：2005.1.7