2-Chlor-4'-methyl-desoxybenzoin | 41840-94-2

• 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-Chlor-4'-methyl-desoxybenzoin
• 英文别名: 2-(2-chlorophenyl)-1-p-tolylethanone；Ethanone, 2-(2-chlorophenyl)-1-(4-methylphenyl)-；2-(2-chlorophenyl)-1-(4-methylphenyl)ethanone
• CAS: 41840-94-2
• 化学式: C₁₅H₁₃ClO
• mdl: MFCD11210894
• 分子量: 244.721
• InChiKey: VVBUKAZKJLSCFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 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-Chlor-4'-methyl-desoxybenzoin 在 溴 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.5h， 生成 2-(2-chlorophenyl)-3-(4-methylphenyl)-5-nitroimidazo[2,1-b][1,3]benzothiazole
  参考文献：
  名称：

  Synthesis and Preliminary In-Vitro Cytotoxic Activity of Novel Substituted diaryl-imidazo [2,1,b]-benzothiazole Derivatives

  摘要：

  通过2-氨基苯并噻唑衍生物（3a-g）与取代α-溴-1,2-取代二苯基-1-乙酮（7a-i）的缩合反应，合成了一系列新型取代二苯并咪唑[2,1-b]苯并噻唑衍生物（8a-y）。通过IR、1H NMR、13C NMR和质谱数据确定了合成化合物的结构。利用MTT法评估了化合物（8a-y）对小鼠（B16F10）和人（MCF-7）癌细胞的体外细胞毒活性。从体外研究中发现，化合物8p、8u和8y最为有效，对MCF-7细胞的IC50范围为0.56-27.50 μM，对B16F10细胞的IC50范围为2.57-36.54 μM。

  DOI：

  10.2174/157018011796576015
• 作为产物：
  描述：

  邻氯苯乙酸 在 吡啶 、 iron(III) chloride 、 三聚氯氰 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 生成 2-Chlor-4'-methyl-desoxybenzoin
  参考文献：
  名称：

  Synthesis of (2-chlorophenyl)(phenyl)methanones and 2-(2-chlorophenyl)-1-phenylethanones by Friedel–Crafts acylation of 2-chlorobenzoic acids and 2-(2-chlorophenyl)acetic acids using microwave heating

  摘要：

  Several 2-(2-chlorophenyl)-1-phenylethanones and (2-chlorophenyl)(phenyl)methanones were prepared by the Friedel-Crafts acylation reaction of 2-(2-chlorophenyl) acetic acids and 2-chlorocarboxylic acids, respectively, in the presence of cyanuric chloride, pyridine, and AlCl(3) or FeCl(3) using microwave heating. The yields of the ketones were significantly higher than those obtained using conventional heating. In addition, similar reactions carried out with the less inexpensive and less toxic FeCl(3) gave titled ketones in comparable yields. Interestingly, the FeCl(3) catalyzed reactions gave pure ketones (no chromatographic purification required), whereas the AlCl(3) catalyzed reaction gave impure product that required chromatographic purification. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.052

文献信息

• Catalytic mutual multicomponent reaction: facile access to α-trifluoromethylthiolated ketones
  作者：Ming Yu Jin、Xiaodong Gu、Min Deng、Chuancheng Wang、Jun (Joelle) Wang

  DOI：10.1039/d0cc04555a

  日期：——

  A multicomponent catalytic reaction between ketones, Morita–Baylis–Hillman (MBH) carbonates and trifluoromethylthiolating agents is devised for straightforwardly accessing two products, α-trifluoromethylthiolated ketones and α-methylene β-amino esters in a one pot fashion. Particularly noteworthy is that the trifluoromethylthiolating reagent is employed as both the nitrogen and SCF3 source initiated

  设计了酮，森田-贝利斯-希尔曼（MBH）碳酸酯和三氟甲基硫醇化剂之间的多组分催化反应，以一种简单的方式直接获得两种产品，即α-三氟甲基硫醇化酮和α-亚甲基β-氨基酯。特别值得注意的是，三氟甲基硫醇化试剂同时被用作由DABCO引发的氮源和SCF 3源。这种温和的一锅策略在将SCF 3基团直接引入各种无环酮上享有原子和阶梯经济吸引力，这些无环酮被认为是效果较差且开发较差的底物。
• Malik, Jitender K.; Noolvi, Malleshappa N.; Manvi, Fakkirappa V., Letters in drug design and discovery, 2011, vol. 8, # 9, p. 717 - 724
  作者：Malik, Jitender K.、Noolvi, Malleshappa N.、Manvi, Fakkirappa V.、Nanjwade、Patel, Harun M.、Manjula、Rao, Mallikarjuna C.、Barve, Ashutosh

  DOI：——

  日期：——
• Pd-catalyzed synthesis of α-aryl ketones through couplings of α-arylacetyl chlorides with triarylbismuths as multi-coupling nucleophiles
  作者：Maddali L.N. Rao、Somnath Giri、Deepak N. Jadhav

  DOI：10.1016/j.tetlet.2009.08.074

  日期：2009.11

  The cross-coupling reaction of alpha-arylacetyl chlorides with triarylbismuths was studied under Pd-catalyzed conditions. The reaction was found to be facile under the established protocol and furnished high yields of alpha-aryl ketones in short reaction times. This work also demonstrated a facile synthesis of various regio-isomeric mono-, di- and tri-substituted alpha-aryl ketones in high yields. Triarylbisrnuths were employed as sub-stoichiometric multi-coupling organometallic nucleophiles in this coupling protocol. (C) 2009 Elsevier Ltd. All rights reserved.
• Shirude; Patel; Giridhar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 4, p. 1080 - 1085
  作者：Shirude、Patel、Giridhar、Yadav

  DOI：——

  日期：——
• Synthesis of (2-chlorophenyl)(phenyl)methanones and 2-(2-chlorophenyl)-1-phenylethanones by Friedel–Crafts acylation of 2-chlorobenzoic acids and 2-(2-chlorophenyl)acetic acids using microwave heating
  作者：Jasia Mahdi、Haribabu Ankati、Jill Gregory、Brian Tenner、Edward R. Biehl

  DOI：10.1016/j.tetlet.2011.03.052

  日期：2011.5

  Several 2-(2-chlorophenyl)-1-phenylethanones and (2-chlorophenyl)(phenyl)methanones were prepared by the Friedel-Crafts acylation reaction of 2-(2-chlorophenyl) acetic acids and 2-chlorocarboxylic acids, respectively, in the presence of cyanuric chloride, pyridine, and AlCl(3) or FeCl(3) using microwave heating. The yields of the ketones were significantly higher than those obtained using conventional heating. In addition, similar reactions carried out with the less inexpensive and less toxic FeCl(3) gave titled ketones in comparable yields. Interestingly, the FeCl(3) catalyzed reactions gave pure ketones (no chromatographic purification required), whereas the AlCl(3) catalyzed reaction gave impure product that required chromatographic purification. (C) 2011 Elsevier Ltd. All rights reserved.