2-oxo-1,2-diphenylethyl 4-chlorobenzoate | 114678-98-7

• 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-oxo-1,2-diphenylethyl 4-chlorobenzoate
• 英文别名: (2-Oxo-1,2-diphenylethyl) 4-chlorobenzoate
• CAS: 114678-98-7
• 化学式: C₂₁H₁₅ClO₃
• 分子量: 350.801
• InChiKey: YTEZSLKJBXSBOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxo-1,2-diphenylethyl 4-chlorobenzoate 在 sodium hydride 、 magnesium 作用下， 以 苯 为溶剂， 反应 42.5h， 生成 α,β-stilbenediol bis(p-chlorobenzoate)
  参考文献：
  名称：

  Equilibria among anions of .alpha.-hydroxy .beta.-diketones and .alpha.-ketol esters

  摘要：

  DOI：

  10.1021/jo00249a043
• 作为产物：
  描述：

  安息香精油 、 4-氯苯甲酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以71%的产率得到2-oxo-1,2-diphenylethyl 4-chlorobenzoate
  参考文献：
  名称：

  Molecular modeling based approach, synthesis, and cytotoxic activity of novel benzoin derivatives targeting phosphoinostide 3-kinase (PI3Kα)

  摘要：

  The oncogenic potential of phosphatidylinositol 3-kinase (PI3K alpha) has made it an attractive target for anticancer drug design. In this work, we describe our efforts to optimize the lead PI3K alpha inhibitor 2-hydroxy-1,2-diphenylethanone (benzoin). A series of 2-oxo-1,2-diphenylethyl benzoate analogs were identified as potential PI3K alpha inhibitors. Docking studies confirmed that the aromatic interaction is mediating ligand/protein complex formation and identified Lys802 and Val851 as H-bonding key residues. Our biological data in human colon carcinoma HCT116 showed that the structure analogs inhibited cell proliferation and induced apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.011

文献信息

• Divergent Synthesis of α-Aroyloxy Ketones and Indenones: A Controlled Domino Radical Reaction for Di- and Trifunctionalization of Alkynes
  作者：Farnaz Jafarpour、Meysam Azizzade、Yekta Golpazir-Sorkheh、Hamed Navid、Saideh Rajai-Daryasarei

  DOI：10.1021/acs.joc.0c00967

  日期：2020.6.19

  Three different modes of aldehyde/alkyne assembly through a controlled radical reaction are devised. While a double C–H activation/annulation leads to indenones, a concurrent oxidation of both aldehydes and alkynes in the course of their connection offers aroyloxy ketones. Besides two types of cascade reactions starting from identical materials, through a phenylpropiolic acid substrate, a cascade three

  设计了通过受控的自由基反应的醛/炔烃组装的三种不同模式。虽然两次C–H活化/环化会导致茚满，但醛和炔烃在其连接过程中同时氧化会产生芳酰氧基酮。除了从相同材料开始的两种类型的级联反应，通过苯丙酸底物外，还通过不间断的C–H功能化/环化/脱羧芳基化形成级联的3个C–C键，这是自由基反应中的一个艰巨挑战，它会产生2-芳酰基-3-芳基茚满。
• SHENOY, G. R.;RANGNEKAR, D. W., DYES AND PIGM., 10,(1989) N, C. 165-172
  作者：SHENOY, G. R.、RANGNEKAR, D. W.

  DOI：——

  日期：——
• RUBIN, MORDECAI B.;INBAR, SHAI, J. ORG. CHEM., 53,(1988) N 14, 3355-3358
  作者：RUBIN, MORDECAI B.、INBAR, SHAI

  DOI：——

  日期：——
• Equilibria among anions of .alpha.-hydroxy .beta.-diketones and .alpha.-ketol esters
  作者：Mordecai B. Rubin、Shai Inbar

  DOI：10.1021/jo00249a043

  日期：1988.7
• Molecular modeling based approach, synthesis, and cytotoxic activity of novel benzoin derivatives targeting phosphoinostide 3-kinase (PI3Kα)
  作者：Dima A. Sabbah、Musaab Saada、Reema Abu Khalaf、Sanaa Bardaweel、Kamal Sweidan、Tariq Al-Qirim、Amani Al-Zughier、Heba Abdel Halim、Ghassan Abu Sheikha

  DOI：10.1016/j.bmcl.2015.06.011

  日期：2015.8

  The oncogenic potential of phosphatidylinositol 3-kinase (PI3K alpha) has made it an attractive target for anticancer drug design. In this work, we describe our efforts to optimize the lead PI3K alpha inhibitor 2-hydroxy-1,2-diphenylethanone (benzoin). A series of 2-oxo-1,2-diphenylethyl benzoate analogs were identified as potential PI3K alpha inhibitors. Docking studies confirmed that the aromatic interaction is mediating ligand/protein complex formation and identified Lys802 and Val851 as H-bonding key residues. Our biological data in human colon carcinoma HCT116 showed that the structure analogs inhibited cell proliferation and induced apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.