(E)-3-(4-chlorophenyl)-1-(2-methoxyphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(4-chlorophenyl)-1-(2-methoxyphenyl)prop-2-en-1-one
• 英文别名: (2E)-3-(4-Chlorophenyl)-1-(2-methoxyphenyl)prop-2-en-1-one
• 化学式: C₁₆H₁₃ClO₂
• 分子量: 272.731
• InChiKey: ISJRFVKFQCRHMN-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-chlorophenyl)-1-(2-methoxyphenyl)prop-2-en-1-one 、 2-氯苯肼盐酸盐 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以41%的产率得到1-(2-chlorophenyl)-5-(4-chlorophenyl)-3-(2-methoxyphenyl)-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Trisubstituted and tetrasubstituted pyrazolines as a novel class of cell-growth inhibitors in tumor cells with wild type p53

  摘要：

  Derivatives with scaffolds of 1,3,5-tri-substituted pyrazoline and 1,3,4,5-tetra-substituted pyrazoline were synthesized and tested for their inhibitory effects versus the p53(+/+) HCT116 and p53 (/) H1299 human tumor cell lines. Several compounds were active against the two cell lines displaying IC50 values in the low micromolar range with a clearly more pronounced effect on the p53(+/+) HCT116 cells. The compound class shows excellent developability due to the modular synthesis, allowing independent optimization of all three to four key substituents to improve the properties of the molecules. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.055
• 作为产物：
  描述：

  2'-甲氧基苯乙酮 、 4-氯苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以72%的产率得到(E)-3-(4-chlorophenyl)-1-(2-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Rh(III)-催化烯酮羰基/酮导向的有氧 C-H 烯烃与未活化烯烃的芳烃

  摘要：

  已经开发了一种 Rh(III) 催化的弱烯酮羰基/酮辅助的芳烃与未活化烯烃的好氧氧化 C-H 烯化。该协议涉及各种取代的生物相关查尔酮和芳香酮（如苯乙酮和色酮）与各种功能化未活化烯烃的交叉脱氢 Heck 型烯化反应，产率适中至良好。此外，还证明了查尔酮与降冰片烯的邻位烷基化。氘标记研究提出并支持了一种可能的反应机制，涉及弱螯合辅助的 C-H 活化/插入/β-氢化物消除。

  DOI：

  10.1021/acs.joc.2c01730

文献信息

• Antiproliferative properties of piperidinylchalcones
  作者：Xiaoling Liu、Mei-Lin Go

  DOI：10.1016/j.bmc.2005.08.006

  日期：2006.1

  Methoxylated chalcones bearing N-methylpiperidinyl substituents oil ring A inhibited the growth of human tumour cell lines (MCF, HCT 116, and Jurkat) at IC50 values or < 5 mu M. Investigations oil a representative member (12) showed that antiproliferative activity was linked to the disruption of the cell cycle at G1 and G2/M phases. The effect was concentration dependent and was evident at the approximate IC50 of 12. Down regulation of cell cycle regulatory components (CDK4, cyclin B, E2F, and phosphorylated Rb) were observed under similar conditions. Methoxylated chalconcs without the piperidinyl substituent were found to exert equally potent and selective antiproliferative activity against HCT 116 tumour cells but did not interfere with cell cycle progression at their IC50 concentrations. The presence of the piperidinyl substituent in the chalcone template is proposed to lend specificity to the mechanism of antiproliferative activity, in addition to promoting a more desirable physicochemical profile. (c) 2005 Elsevier Ltd. All rights reserved.
• Stereoselective One-Pot Synthesis of Oxazolines
  作者：Saumen Hajra、Sukanta Bar、Debarshi Sinha、Biswajit Maji

  DOI：10.1021/jo8003937

  日期：2008.6.1

  Treatment of alkenes with NBS, a nitrile, NaHCO3 and water in the presence of Cu(OTf)(2) or Zn(OTf)(2) is reported to furnish oxazolines in one pot and good yields. The reaction is equally applicable to chalcones.
• Solvent free synthesis of 1,3-diaryl-2-propenones catalyzed by commercial acid-clays under ultrasound irradiation
  作者：Manef Chtourou、Rami Abdelhédi、Mohamed Hédi Frikha、Mahmoud Trabelsi

  DOI：10.1016/j.ultsonch.2009.06.008

  日期：2010.1

  This paper presents a novel solvent free method of synthesis of trans-chalcones. The method was based on ultrasound irradiation of the reagents (aryl methyl ketones and aryl aldehydes) in presence of commercial acid-montmorillonites as catalysts. The trans-chalcones were synthesized in high yields (85-95%) and excellent selectivity in a short reaction time. (C) 2009 Elsevier B.V. All rights reserved.
• Trisubstituted and tetrasubstituted pyrazolines as a novel class of cell-growth inhibitors in tumor cells with wild type p53
  作者：Mohammad Abdel-Halim、Adam B. Keeton、Evrim Gurpinar、Bernard D. Gary、Simon M. Vogel、Matthias Engel、Gary A. Piazza、Frank M. Boeckler、Rolf W. Hartmann、Ashraf H. Abadi

  DOI：10.1016/j.bmc.2013.09.055

  日期：2013.12

  Derivatives with scaffolds of 1,3,5-tri-substituted pyrazoline and 1,3,4,5-tetra-substituted pyrazoline were synthesized and tested for their inhibitory effects versus the p53(+/+) HCT116 and p53 (/) H1299 human tumor cell lines. Several compounds were active against the two cell lines displaying IC50 values in the low micromolar range with a clearly more pronounced effect on the p53(+/+) HCT116 cells. The compound class shows excellent developability due to the modular synthesis, allowing independent optimization of all three to four key substituents to improve the properties of the molecules. (C) 2013 Elsevier Ltd. All rights reserved.
• Rh(III)-Catalyzed Enone Carbonyl/Ketone-Directed Aerobic C–H Olefination of Aromatics with Unactivated Olefins
  作者：Chikkabagilu Nagaraju Shambhavi、Masilamani Jeganmohan

  DOI：10.1021/acs.joc.2c01730

  日期：2022.10.7

  carbonyl/ketone-assisted aerobic oxidative C–H olefination of aromatics with unactivated alkenes has been developed. This protocol involves cross-dehydrogenative Heck-type olefination reaction of various substituted biologically relevant chalcones and aromatic ketones such as acetophenones and chromones with various functionalized unactivated olefins in moderate to good yields. Further, ortho-alkylation of chalcones

  已经开发了一种 Rh(III) 催化的弱烯酮羰基/酮辅助的芳烃与未活化烯烃的好氧氧化 C-H 烯化。该协议涉及各种取代的生物相关查尔酮和芳香酮（如苯乙酮和色酮）与各种功能化未活化烯烃的交叉脱氢 Heck 型烯化反应，产率适中至良好。此外，还证明了查尔酮与降冰片烯的邻位烷基化。氘标记研究提出并支持了一种可能的反应机制，涉及弱螯合辅助的 C-H 活化/插入/β-氢化物消除。