2-(2-bromophenylmethyl)cycloheptanone | 132452-19-8

• 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-bromophenylmethyl)cycloheptanone
• 英文别名: 2-[(2-Bromophenyl)methyl]cycloheptanone；2-[(2-bromophenyl)methyl]cycloheptan-1-one
• CAS: 132452-19-8
• 化学式: C₁₄H₁₇BrO
• 分子量: 281.192
• InChiKey: LITPLMGIYXVGHE-UHFFFAOYSA-N

物化性质

• 沸点：
  370.3±15.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-bromophenylmethyl)cycloheptanone 生成 2-(o-Bromobenzyl)-1-methylenecycloheptane
  参考文献：
  名称：

  Pal Sitaram, Mukhopadhyaya Jayanta K., Ghatak Usha Ranjan, J. Org. Chem, 59 (1994) N 10, S 2687-2694

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氧代环庚烷甲酸乙酯 在 盐酸 、 sodium 、 溶剂黄146 作用下， 以 水 、 苯 为溶剂， 反应 34.0h， 生成 2-(2-bromophenylmethyl)cycloheptanone
  参考文献：
  名称：

  Regioselective Aryl Radical Cyclization. 1. Stereocontrolled Synthesis of Linearly Condensed Hydroaromatic Carbocyclic Systems through 6-endo-Ring Closures

  摘要：

  The stereocontrolled synthesis of trans-octahydroanthracenes 3, 11a-c, and 14a-c and trans-octahydro-5aH-cyclohepta[b] naphthalene (27) through implementation of an efficient and highly regioselective 6-endo-trig-aryl radical cyclization of the respective 2-(o-bromoaryl)-1-methylenecyclohexanes 2, 10a-c, and 13a-c and 2-(o-bromobenzyl)-1-methylenecycloheptane (41) with tri-n- butyltin-hydride-is described. The radical cyclization of 2-(o-bromobenzyl)-1-methylenecyclopentane (43), in contrast, produced a mixture of the cis- and trans-hexahydro-1H-benz[f]indenes (38) and (37).

  DOI：

  10.1021/jo00089a009

文献信息

• Palladium-Catalyzed Cross-Coupling of Cyclopropanols with Aryl Halides Under Mild Conditions
  作者：David Rosa、Arturo Orellana

  DOI：10.1021/ol1026409

  日期：2011.1.7

  Intra- and intermolecular palladium-catalyzed cross-coupling of cyclopropanols with aryl halides can be achieved in good yields under mild conditions.

  在温和条件下，可以高收率实现环丙醇与芳基卤化物在分子内和分子间钯催化的交叉偶联。
• Efficient synthesis of 2- and 3-substituted indenes from 2-bromobenzyl bromide through an enolate alkylation/Cr(II)/Ni(II)-mediated carbonyl addition sequence
  作者：Ronald L. Halterman、Chengian Zhu

  DOI：10.1016/s0040-4039(99)01541-5

  日期：1999.10

  efficient new synthesis of 2- and 3-substituted indenes has been developed based on the nickel-catalyzed chromium(II)-promoted addition of aryl bromides to a tethered ketone carbonyl. Several tethered bromoaryl ketones were prepared through enolate alkylation of acyclic or cyclic ketones with 2-bromobenzyl bromide. Nozaki-Takai-Hiyama-Kishi closure of the resulting bromoaryl ketones followed by acid promoted

  基于镍催化的铬（II）促进的芳基溴化物向束缚的酮羰基的加成反应，已开发出一种有效的新合成2-和3-取代的茚基的方法。通过用2-溴苄基溴对无环或环状酮进行烯丙基化烷基化反应，制得了几种束缚的溴代芳基酮。所得到的溴芳基酮的Nozaki-Takai-Hiyama-Kishi封闭，然后酸促进的脱水作用，使三步顺序的总收率得到取代的茚满，收率范围为29％至58％。
• Polycyclic amines useful as cerebrovascular agents
  申请人：——

  公开号：US05071853A1

  公开（公告）日：1991-12-10

  A novel series of polycyclic amines, derivatives, methods of making the compounds, novel intermediates, compositions containing them, and methods for using them in the treatment and prevention of cerebrovascular disorders are disclosed.

  揭示了一种新的多环胺类化合物系列，其衍生物，制备这些化合物的方法，新的中间体，含有它们的组合物，以及在治疗和预防脑血管疾病中使用它们的方法。
• Palladium-catalyzed intramolecular α-arylation of aliphatic ketone, formyl, and nitro groups
  作者：Hideaki Muratake、Mitsutaka Natsume、Hiroshi Nakai

  DOI：10.1016/j.tet.2004.09.112

  日期：2004.12

  Intramolecular arylation of properly designed substrates bearing a ketone, formyl, or nitro terminating group was achieved by use of a PdCl2(Ph3P)2–Cs2CO3 reaction system to form a variety of carbocyclic compounds. Arylation in ketone compounds afforded benzene-annulated bridged or spirocycloalkanone derivatives, depending on the structure of the cyclization precursors. Arylation in formyl compounds

  通过使用PdCl 2（Ph 3 P）2 -Cs 2 CO 3，对设计适当的带有酮，甲酰基或硝基终止基团的底物进行分子内芳构化反应体系形成各种碳环化合物。取决于环化前体的结构，酮化合物中的芳基化可提供苯环化的桥环或螺环烷酮衍生物。取决于环化前体的结构和反应溶剂，甲酰基化合物中的芳基化发生在α位置（α-芳基化）或羰基碳（羰基芳基化）。α-芳基化的仲硝基以Nef反应的方式部分转化为酮，而叔硝基被部分消除，得到苯乙烯型烯烃。
• Synthesis and pharmacological evaluation of hexahydrofluorenamines as noncompetitive antagonists at the N-methyl-D-aspartate receptor
  作者：Sheryl J. Hays、Perry M. Novak、Daniel F. Ortwine、Christopher F. Bigge、Norman L. Colbry、Graham Johnson、Leonard J. Lescosky、Thomas C. Malone、Andre Michael

  DOI：10.1021/jm00058a002

  日期：1993.3

  optimal affinity concentrated in analogs containing a heteroatom (sulfur) in the B ring (IC50 of 11 nM versus [3H]TCP for 16b), methyl substitution on the amine, and R stereochemistry at the 4a position. No significant improvement in affinity was seen with aromatic ring substitution. Aliphatic ring substitution, large amine substituents, and alterations in the position of amine substitution on the ring

  N-甲基-D-天冬氨酸（NMDA）受体复合物的非竞争性（PCP）位点涉及多种病理，包括缺血性中风的病因。最近的测试表明，PCP的刚性类似物cis-1,2,3,4,9,9a-六氢-N-甲基-4aH-芴-4a-胺（1）在该部位是有效的拮抗剂（对于[3H] TCP置换，IC50 = 30 nM。基于该发现，已经制备了涵盖立体化学，胺取代和位置，芳族和脂族环取代以及杂原子环取代的变化的许多衍生物，以探索该环系统周围的构效关系。评估所有化合物的PCP受体亲和力；还在体外（培养的神经元）和体内（预防了NMDA诱导的小鼠致死性）中测试了有效的化合物。本六氢氟胺显示出广泛的效价，其最佳亲和力集中于在B环中包含杂原子（硫）的类似物（IC50为11 nM，而[3H] TCP为16b），胺上的甲基取代和R上的立体化学。 4a位置。用芳环取代没有观察到亲和力的显着改善。脂族环取代，大的胺取代基和胺取代在环系统上的