2-(benzylsulfanyl)-1-(4-chlorophenyl)ethanone | 52264-85-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(benzylsulfanyl)-1-(4-chlorophenyl)ethanone
• 英文别名: 2-(benzylthio)-1-(4-chlorophenyl)ethanone；2-(benzylthio)-4'-chloroacetophenone；benzyl p-chlorophenacyl sulphide；2-Benzylsulfanyl-1-(4-chlorophenyl)ethanone
• CAS: 52264-85-4
• 化学式: C₁₅H₁₃ClOS
• mdl: MFCD01603690
• 分子量: 276.787
• InChiKey: SZFDJIAWFRURCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzylsulfanyl)-1-(4-chlorophenyl)ethanone 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 Alpha,alpha-dichloro-alpha-(4-chlorobenzoyl)-methane-sulfenyl chloride
  参考文献：
  名称：

  Synthesis of .alpha.,.alpha.-dichlorosulfenyl chlorides

  摘要：

  DOI：

  10.1021/jo00820a016
• 作为产物：
  描述：

  2'-甲基乙酰乙酰苯胺 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.83h， 生成 2-(benzylsulfanyl)-1-(4-chlorophenyl)ethanone
  参考文献：
  名称：

  使用2- [双（双（烷硫基亚甲基）亚甲基] -3-氧代-N-邻甲苯基丁酰胺）硫醇当量高效无臭地合成硫醚

  摘要：

  使用2- [双（烷硫基）亚甲基] -3-氧代- ñ - ö -tolylbutanamides 1为无臭硫醇当量，硫醚的有效和无臭的合成已经研制成功。在EtOH中由NaOH促进，裂解1开始生成硫醇根阴离子，然后生成的硫醇根阴离子与卤化物反应生成各种硫醚，收率很高。值得注意的是，在反应和后处理过程中都只能感觉到非常微弱的硫醇气味。

  DOI：

  10.1002/cjoc.201100096

文献信息

• Enantioselective Synthesis of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation: A Facile Approach to the Preparation of Chiral Allylic and Homoallylic Compounds
  作者：Taigang Zhou、Byron Peters、Matías F. Maldonado、Thavendran Govender、Pher G. Andersson

  DOI：10.1021/ja306731u

  日期：2012.8.22

  A highly efficient and enantioselective Ir-catalyzed hydrogenation of unsaturated sulfones was developed. Chiral cyclic and acyclic sulfones were produced in excellent enantioselectivities (up to 98% ee). Coupled with the Ramberg-Bäcklund rearrangement, this reaction offers a novel route to chiral allylic and homoallylic compounds in excellent enantioselectivities (up to 97% ee) and high yields (up

  开发了一种高效且对映选择性 Ir 催化的不饱和砜加氢反应。以优异的对映选择性（高达 98% ee）生产手性环状和无环砜。与 Ramberg-Bäcklund 重排相结合，该反应提供了一种获得具有优异对映选择性（高达 97% ee）和高产率（高达 94%）的手性烯丙基和同型烯丙基化合物的新途径。
• Arora, Kanwar J. S.; Collier, John R.; Deodhar, Dinker J., Journal of Chemical Research, Miniprint, 1985, # 6, p. 2148 - 2183
  作者：Arora, Kanwar J. S.、Collier, John R.、Deodhar, Dinker J.、Hesabi, Masoud-M.、Hill, John

  DOI：——

  日期：——
• Design, synthesis and biological evaluation of novel (E)-α-benzylsulfonyl chalcone derivatives as potential BRAF inhibitors
  作者：Qing-Shan Li、Cui-Yun Li、Xiang Lu、Hui Zhang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2012.02.007

  日期：2012.4

  Activating mutations in the BRAF serine/threonine kinase are found in more than 70% of human melanomas, >90% of which are BRAF(V600E). It provides new therapeutic opportunities in malignant melanoma. In silico and in vitro screening of our compound collection has identified Hit 2 as BRAF(V600E) inhibitor. Based on its structure, a series of novel (E)-alpha-benzylsulfonyl chalcone derivatives (13-40) were designed and synthesized. Compound 38 exhibited the most potent inhibitory activity with an IC50 value of 0.17 mu M for BRAF(V600E) and GI(50) value of 0.52 mu M for mutant BRAF-dependent cells. The results of cell based pERK activity and cellular selectivity suggested that those compounds could selectively inhibit proliferation of mutant BRAF-dependent melanoma cell line through inhibition of oncogenic BRAF. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Singh, Harjit; Malhotra, Nageshwar; Batra, Manohar S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 4, p. 272 - 273
  作者：Singh, Harjit、Malhotra, Nageshwar、Batra, Manohar S.

  DOI：——

  日期：——
• Singh, Harjit; Batra, Manohar S.; Singh, Paramjit, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 131 - 136
  作者：Singh, Harjit、Batra, Manohar S.、Singh, Paramjit

  DOI：——

  日期：——