(3-溴苯基)(环戊基)甲酮 | 898791-44-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3-溴苯基)(环戊基)甲酮
• 英文名称: (3-bromophenyl)(cyclopentyl)methanone
• 英文别名: (3-bromophenyl)cyclopentylmethanone；3-Bromophenyl cyclopentyl ketone；(3-bromophenyl)-cyclopentylmethanone
• CAS: 898791-44-1
• 化学式: C₁₂H₁₃BrO
• 分子量: 253.139
• InChiKey: VGGBIJBPTCLCPI-UHFFFAOYSA-N

物化性质

• 沸点：
  335.5±25.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  2
• 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

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  (3-溴苯基)(环戊基)甲酮 在 苯硅烷 、 copper(II) acetate monohydrate 、 (R)-(+)-2,2’,6,6’-四甲氧基-4,4’-联(二(3,5-二甲苯基基)膦基)-3,3’-二联吡啶 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以96%的产率得到(-)-(3-bromophenyl)cyclopentylmethanol
  参考文献：
  名称：

  铜-二吡啶基膦催化的氢化硅烷化：芳基和杂芳基环烷基醇的对映选择性合成†

  摘要：

  首次系统地研究了非贵金属铜催化的各种不同环尺寸的芳基环烷基酮的对映选择性氢化硅烷化（对映体过量高达99％）。结果表明，环烷基的空间大小对反应结果有重要影响。还实现了对映体纯度高达97％的环己基杂芳基醇的选择的首次立体选择性形成。在某些环己基吡啶基酮的还原中，观察到温度对醇产物的对映体纯度和绝对构型都有显着影响。

  DOI：

  10.1039/c2ob27040d
• 作为产物：
  描述：

  间溴苯甲醛 、 环戊烷 在 二叔丁基过氧化物 作用下， 反应 1.0h， 以38%的产率得到(3-溴苯基)(环戊基)甲酮
  参考文献：
  名称：

  Synthesis of Ketones through Microwave Irradiation Promoted Metal-Free Alkylation of Aldehydes by Activation of C(sp³)–H Bond

  摘要：

  In this paper, a novel methodology for the synthesis of ketones via microwave irradiation promoted direct alkylation of aldehydes by activation of the inert C(sp(3))-H bond has been developed. Notably, the reactions were accomplished under metal-free conditions and used commercially available aldehydes and cycloalkanes as substrates without prefunctionalization. By using this novel method, an alternative synthetic approach toward the key intermediates for the preparation of the pharmaceutically valuable oxaspiroketone derivatives was successfully established.

  DOI：

  10.1021/acs.joc.5b01824

文献信息

• Radical Catalysis of Kumada Cross-Coupling Reactions Using Functionalized Grignard Reagents
  作者：Georg Manolikakes、Paul Knochel

  DOI：10.1002/anie.200803730

  日期：2009.1

  Palladium, radically different: A wide range of polyfunctional aryl‐ and heteroarylmagnesium reagents undergo fast Kumada cross‐couplings (see scheme) with functionalized aryl bromides in the presence of a palladium catalyst and an alkyl iodide as additive. These reactions proceed by a radical pathway.

  钯，根本不同：在钯催化剂和烷基碘化物的存在下，多种多官能芳基镁和杂芳基镁试剂与功能化芳基溴化物快速进行Kumada交叉偶联（参见方案）。这些反应通过自由基途径进行。
• Structure based design of iminohydantoin BACE1 inhibitors: Identification of an orally available, centrally active BACE1 inhibitor
  作者：Jared N. Cumming、Elizabeth M. Smith、Lingyan Wang、Jeffrey Misiaszek、James Durkin、Jianping Pan、Ulrich Iserloh、Yusheng Wu、Zhaoning Zhu、Corey Strickland、Johannes Voigt、Xia Chen、Matthew E. Kennedy、Reshma Kuvelkar、Lynn A. Hyde、Kathleen Cox、Leonard Favreau、Michael F. Czarniecki、William J. Greenlee、Brian A. McKittrick、Eric M. Parker、Andrew W. Stamford

  DOI：10.1016/j.bmcl.2012.02.013

  日期：2012.4

  From an initial lead 1, a structure-based design approach led to identification of a novel, high-affinity iminohydantoin BACE1 inhibitor that lowers CNS-derived Ab following oral administration to rats. Herein we report SAR development in the S3 and F' subsites of BACE1 for this series, the synthetic approaches employed in this effort, and in vivo data for the optimized compound. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of Ketones through Microwave Irradiation Promoted Metal-Free Alkylation of Aldehydes by Activation of C(sp³)–H Bond
  作者：Xinying Zhang、Zhangxin Wang、Xuesen Fan、Jianji Wang

  DOI：10.1021/acs.joc.5b01824

  日期：2015.11.6

  In this paper, a novel methodology for the synthesis of ketones via microwave irradiation promoted direct alkylation of aldehydes by activation of the inert C(sp(3))-H bond has been developed. Notably, the reactions were accomplished under metal-free conditions and used commercially available aldehydes and cycloalkanes as substrates without prefunctionalization. By using this novel method, an alternative synthetic approach toward the key intermediates for the preparation of the pharmaceutically valuable oxaspiroketone derivatives was successfully established.
• Copper-dipyridylphosphine-catalyzed hydrosilylation: enantioselective synthesis of aryl- and heteroarylcycloalkyl alcohols
  作者：Shan-Bin Qi、Min Li、Shijun Li、Ji-Ning Zhou、Jun-Wen Wu、Feng Yu、Xi-Chang Zhang、Albert S. C. Chan、Jing Wu

  DOI：10.1039/c2ob27040d

  日期：——

  hydrosilylation of a vast array of aryl cycloalkyl ketones with different ring sizes was studied systematically for the first time (up to 99% enantiomeric excess). The results demonstrated that the steric size of cycloalkyl groups has a significant influence on the reaction outcomes. The first stereoselective formation of a selection of cyclohexyl heteroaryl alcohols of up to 97% enantiopurity was realized

  首次系统地研究了非贵金属铜催化的各种不同环尺寸的芳基环烷基酮的对映选择性氢化硅烷化（对映体过量高达99％）。结果表明，环烷基的空间大小对反应结果有重要影响。还实现了对映体纯度高达97％的环己基杂芳基醇的选择的首次立体选择性形成。在某些环己基吡啶基酮的还原中，观察到温度对醇产物的对映体纯度和绝对构型都有显着影响。