2-bromo-1-(naphthalen-2-yl)-2-phenylethan-1-one | 113488-00-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-bromo-1-(naphthalen-2-yl)-2-phenylethan-1-one
• 英文别名: 2-bromo-1(naphthalen-2-yl)-2-phenylethanone；2-bromo-1-(2-naphthyl)-2-phenylethanone；2-bromo-1-[2]naphthyl-2-phenyl-ethanone；(α-Brom-benzyl)-β-naphthyl-keton；2-Brom-1-[2]naphthyl-2-phenyl-aethanon；2-Bromo-1-naphthalen-2-yl-2-phenylethanone
• CAS: 113488-00-9
• 化学式: C₁₈H₁₃BrO
• 分子量: 325.205
• InChiKey: ZOCQWIVCHBCHFT-UHFFFAOYSA-N

物化性质

• 熔点：
  111-111.5 °C
• 沸点：
  438.0±25.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-bromo-1-(naphthalen-2-yl)-2-phenylethan-1-one 在 吡啶 、 高氯酸 、 硫化氢 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.25h， 生成 4-Naphthalen-2-yl-5-phenyl-1,3-dithiol-2-thion
  参考文献：
  名称：

  Fanghaenel; Van Hinh; Schukat, Advanced Synthesis and Catalysis, 1996, vol. 338, # 6, p. 523 - 531

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(naphthalen-2-yl)-2-phenylethan-1-ol 在 溴 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 4.0h， 生成 2-bromo-1-(naphthalen-2-yl)-2-phenylethan-1-one
  参考文献：
  名称：

  3D-QSAR assisted identification of FABP4 inhibitors: An effective scaffold hopping analysis/QSAR evaluation

  摘要：

  Following on the recent publication of pharmacologically relevant effects, small molecule inhibitors of adipocyte fatty-acid binding protein 4 (FABP4) have attracted high interest. FABP4 is mainly expressed in macrophages and adipose tissue, where it regulates fatty acid storage and lipolysis, being also an important mediator of inflammation. In this regard, FABP4 recently demonstrated an interesting molecular target for the treatment of type 2 diabetes, other metabolic diseases and some type of cancers. In the past years, hundreds of effective FABP4 inhibitors have been synthesized. In this paper, a quantitative structure-activity relationship (QSAR) model has been produced, in order to predict the bioactivity of FABP4 inhibitors. The methodology has been combined with a scaffold-hopping approach, allowing to identify three new molecules that act as effective inhibitors of this protein. These molecules, synthesized and tested for their FABP4 inhibitor activity, showed IC(50 )values between 3.70 and 5.59 mu M, with a high level of agreement with the predicted values.

  DOI：

  10.1016/j.bioorg.2018.11.045

文献信息

• BF 3 ·OEt 2 -mediated [1,2]-aryl shift: Synthesis of functionalized α-arylnitriles via the bromination/cyanation/deformylation of substituted deoxybenzoin
  作者：Chieh-Kai Chan、Meng-Yang Chang

  DOI：10.1016/j.tet.2017.07.015

  日期：2017.8

  A new sequential, tandem synthesis of functionalized α-arylnitriles via the bromination/cyanation/deformylation of substituted deoxybenzoin has developed. CuBr2-promoted bromination of substituted deoxybenzoins gives 2-bromo-2-arylacetophenne 3. The cyanation of 3 with sodium cyanide (NaCN) generates epoxynitrile. Then, a treatment of epoxynitrile with BF3·OEt2 results in the formation of functionalized

  通过取代的脱氧安息香素的溴化/氰化/去甲酰基化，开发了一种新的顺序串联的官能化α-芳基腈的合成方法。CuBr 2促进的取代脱氧安息香素的溴化反应生成2-溴-2-芳基乙酰基3。的氰化3用氰化钠（NaCN的）epoxynitrile生成。然后，用BF 3 · OEt 2处理环氧腈导致通过1,2-芳基转移形成官能化的α-芳基腈4。
• Studies in the Cycloproparene Series: Reactions of Alkylidenecycloproparenes With Electrophiles
  作者：SJ Buckland、B Halton、Q Mei、PJ Stang

  DOI：10.1071/ch9871375

  日期：——

  The addition of an electrophile to the alkylidenecycloproparenes (2a-d) is dominated by capture at the exocyclic centre with formation of the corresponding cycloproparenyl cation, e.g. (15). Subsequent reaction with the counter ion is usually accompanied by cleavage of the three-membered ring. Thus compounds (2) give the ethanones (4) with aqueous acids whilst anhydrous acetic acid yields the vinyl acetates (5). Silver(1)-catalysed methanolysis of (2) leads to vinyl ethers (6); the alkyne (7) is formed only from (2d) which carries a vinylic proton. Brominations and bromine water additions lead to products of ring expansion (8)-(10) or ring cleavage (11)-(14) depending upon the conditions employed. These latter reactions demonstrate a delicate balance between cycloproparenylcarbinyl cation formation and cleavage of the three-membered ring.

  亲电体与亚烷基环丙烯酸酯（2a-d）的加成反应主要是捕获外环中心，形成相应的环丙烯酸阳离子，例如 (15)。随后与反离子的反应通常伴随着三元环的裂解。因此，化合物 (2) 与水酸反应可生成乙酮 (4)，而与无水乙酸反应则可生成乙酸乙烯酯 (5)。银(1)催化的(2)甲醇分解可生成乙烯基醚(6)；炔烃(7)仅由携带乙烯基质子的(2d)生成。溴化反应和溴水加成反应会产生扩环（8）-（10）或裂环（11）-（14）产物，具体取决于所采用的条件。后一种反应显示了环丙烯酰基碳酰阳离子形成和三元环裂解之间的微妙平衡。
• Analgesics. III. Hydrochlorides of Phenylalkylamines
  作者：L. H. Goodson、R. B. Moffett

  DOI：10.1021/ja01177a080

  日期：1949.9
• Rossi; Trave, Chimica e l'Industria (Milan, Italy), 1958, vol. 40, p. 827,829
  作者：Rossi、Trave

  DOI：——

  日期：——
• Ruggli; Reinert, Helvetica Chimica Acta, 1926, vol. 9, p. 74
  作者：Ruggli、Reinert

  DOI：——

  日期：——