1-(α-tosyloxy)acetonaphthone | 352517-78-3

• 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: 1-(α-tosyloxy)acetonaphthone
• 英文别名: tosyloxymethyl 1-naphthyl ketone；(2-Naphthalen-1-yl-2-oxoethyl) 4-methylbenzenesulfonate
• CAS: 352517-78-3
• 化学式: C₁₉H₁₆O₄S
• 分子量: 340.4
• InChiKey: BXGFCJUVNRWTTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(α-tosyloxy)acetonaphthone 、 4-氯苯基硫脲 在 potassium carbonate 作用下， 以 neat (no solvent) 为溶剂， 以90%的产率得到2-(4-chlorophenyl)-4-(1-naphthyl)aminothiazole
  参考文献：
  名称：

  Pundeer, Rashmi; Vijaykiran, Indian Journal of Heterocyclic Chemistry, 2016, vol. 25, # 3-4, p. 311 - 315

  摘要：

  DOI：
• 作为产物：
  描述：

  1-萘乙酮 、 羟基甲苯磺酰碘苯 以 二氯甲烷 为溶剂， 反应 4.0h， 以85%的产率得到1-(α-tosyloxy)acetonaphthone
  参考文献：
  名称：

  Pundeer, Rashmi; Vijaykiran, Indian Journal of Heterocyclic Chemistry, 2016, vol. 25, # 3-4, p. 311 - 315

  摘要：

  DOI：

文献信息

• An unprecedented protocol for the synthesis of 3-hydroxy-3-phenacyloxindole derivatives with indolin-2-ones and α-substituted ketones
  作者：Mei Bai、Yong You、Yong-Zheng Chen、Guang-Yan Xiang、Xiao-Ying Xu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1039/c5ob02391b

  日期：——

  An unprecedented reaction between indolin-2-ones and α-substituted ketones has been developed. Using this protocol, a wide range of biologically important 3-hydroxy-3-phenacyloxindole derivatives could be obtained in good yield (up to 93%) under mild reaction conditions. A possible mechanism of this reaction was tentatively proposed based on some control experiments and MS spectrometry analysis.

  已经开发出吲哚-2-酮与α-取代的酮之间空前的反应。使用该协议，可以在温和的反应条件下以良好的收率（高达93％）获得各种各样的生物学上重要的3-羟基-3-苯并恶唑衍生物。根据一些对照实验和质谱分析，初步提出了该反应的可能机理。
• Iodoarene-Mediated α-Tosyloxylation of Ketones with MCPBA and p-Toluenesulfonic Acid
  作者：Hideo Togo、Ayumi Tanaka、Katsuhiko Moriyama

  DOI：10.1055/s-0030-1260948

  日期：2011.8

  Alkyl aryl ketones and dialkyl ketones could be converted into the corresponding α-tosyloxy ketones by the reaction with MCPBA and p-toluenesulfonic acid monohydrate (PTSA˙H2O) in the presence of a catalytic amount of molecular iodine (I2) in a mixture of acetonitrile and 2,2,2-trifluoroethanol, although the yields were dependent on the ketones (method A). The same conversion of alkyl aryl ketones and dialkyl ketones into the corresponding α-­tosyloxy ketones could be smoothly carried out by the reaction with MCPBA and PTSA˙H2O in the presence of catalytic amounts of ­iodine and tert-butylbenzene in a mixture of acetonitrile and 2,2,2-trifluoroethanol (method B). In those reactions, p-iodotoluene and 4-tert-butyl-1-iodobenzene were formed at first in method A and method B, respectively, and then they were converted into p-[(hydroxy)(tosyloxy)]iodotoluene and 4-tert-butyl-1-[(hydroxy)(tosyloxy)iodo]benzene by the reaction with MCPBA and PTSA˙H2O. p-[(Hydroxy)(tosyloxy)]iodotoluene and 4-tert-butyl-1-[(hydroxy)-(tosyloxy)iodo]benzene worked as an α-tosyloxylation reagent of ketones.

  烷基芳基酮和二烷基酮可以通过与间氯过氧苯甲酸（MCPBA）和单水合对甲苯磺酸（PTSA·H2O）在催化量的碘分子（I2）存在下反应，在乙腈和2,2,2-三氟乙醇的混合物中，转化为相应的α-甲苯磺酰氧基酮，尽管产率取决于酮类（方法A）。烷基芳基酮和二烷基酮同样可以通过与MCPBA和PTSA· 在催化量的碘和叔丁基苯存在下反应，在乙腈和2,2,2-三氟乙醇的混合物中，顺利转化为相应的α-甲苯磺酰氧基酮（方法B）。在这些反应中，方法A和方法B分别首先形成对碘甲苯和4-叔丁基-1-碘苯，然后它们通过与MCPBA和PTSA· 反应转化为对[(羟基)(甲苯磺酰氧基)]碘甲苯和4-叔丁基-1-[(羟基)(甲苯磺酰氧基)碘]苯。对[(羟基)(甲苯磺酰氧基)]碘甲苯和4-叔丁基-1-[(羟基)(甲苯磺酰氧基)碘]苯作为酮的α-甲苯磺酰氧化试剂。
• One‐Pot Synthesis of α‐Formyloxy Ketones from Enolizable Ketones
  作者：Sunil Kumar、Ashok Kumar、Rakesh K. Gupta、Devinder Kumar

  DOI：10.1080/00397910701767049

  日期：2008.1.1

  One-pot synthesis of alpha-formyloxy tones as well as alpha-acetoxy ketones from enolizable ketones and [hydroxy(tosyloxy)iodo] benzene (HTIB)/polymer supported [hydroxy(tosyloxy)iodo]benzene (PSHTIB) in N,N - dimethylformamide (DMF)/N,N - dimethylacetamide (DMA) in high yields is described.
• Design, regioselective synthesis and cytotoxic evaluation of 2-aminoimidazole–quinoline hybrids against cancer and primary endothelial cells
  作者：Kuldeep Singh、Vikas Verma、Kavita Yadav、Vedagopuram Sreekanth、Devinder Kumar、Avinash Bajaj、Vinod Kumar

  DOI：10.1016/j.ejmech.2014.09.055

  日期：2014.11

  In search of new selective anti-cancer agents, a series of sixteen novel 2-aminoimidazole quinoline hybrid compounds (5a-5p) have been designed and synthesized regioselectively. We have characterized the compounds extensively using IR, 1D and 2D NMR Spectroscopy and mass spectrometry. The cytotoxicity studies against different cancer cell lines showed that the compound 5a (Imd-Ph) emerged as a potent cytotoxic scaffold. Imd-Ph (5a) exhibited a selective anticancer activity against human colon cancer cell line (HCT-116, DLD-1) and was found relatively non-toxic to breast cancer cells (MDA-MB-231) as well as to normal primary endothelial cells (HUVEC). Structure-activity relationship of imidazole -quinoline hybrid scaffolds revealed differential and selective toxicities exerted by the different derivatives against cancer and normal cells. Structural modification of the scaffold with library of a wide variety of substituents may lead to the development of novel selective anti-cancer agents in the future. (C) 2014 Elsevier Masson SAS. All rights reserved.