(E)-3-(4-fluorophenyl)-1-(2-methoxyphenyl)prop-2-en-1-one | 1029599-27-6

• 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-fluorophenyl)-1-(2-methoxyphenyl)prop-2-en-1-one
• 英文别名: (2E)-3-(4-Fluorophenyl)-1-(2-methoxyphenyl)prop-2-en-1-one
• CAS: 1029599-27-6
• 化学式: C₁₆H₁₃FO₂
• 分子量: 256.276
• InChiKey: ZTSGCLKEJGWBCA-DHZHZOJOSA-N

物化性质

• 沸点：
  397.3±42.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-fluorophenyl)-1-(2-methoxyphenyl)prop-2-en-1-one 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 碳酸氢铵 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以68%的产率得到(Z)-3-amino-3-(4-fluorophenyl)-1-(2-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  三硫-自由基-阴离子引发的缺电子烯烃的C（sp 2）–H胺化

  摘要：

  甲trisulfur自由基-阴离子（š 3＆CenterDot; -）-triggered C（SP 2）-H的α胺化，用简单的胺β不饱和羰基衍生物已被证明。该方案可方便地获得具有绝对Z选择性的多种合成有价值的N-未保护和仲β-烯胺酮，以及具有E选择性的叔β-烯胺酮。机械探针和电子结构理论计算表明该S 3＆CenterDot; -发起经由硫杂丙环亲核攻击中间。

  DOI：

  10.1021/acs.orglett.0c03846
• 作为产物：
  描述：

  2'-甲氧基苯乙酮 、 对氟苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以76%的产率得到(E)-3-(4-fluorophenyl)-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

• Development of a Formal Catalytic Asymmetric [4 + 2] Addition of Ethyl-2,3-butadienoate with Acyclic Enones
  作者：Kumar Dilip Ashtekar、Richard J. Staples、Babak Borhan

  DOI：10.1021/ol202301f

  日期：2011.11.4

  Allene esters are unique not only as excellent electrophiles but also because of their ability for subsequent reactivity after the initial nucleophilic attack. A mechanistically inspired cyclization using ethyl-2,3-butadienoate and acyclic enones to provide dihydropyrans In excellent yields and enantioselectivity under solvent-free conditions at room temperature is reported.
• Chalcones with electron-withdrawing and electron-donating substituents: Anticancer activity against TRAIL resistant cancer cells, structure–activity relationship analysis and regulation of apoptotic proteins
  作者：Chun Wai Mai、Marzieh Yaeghoobi、Noorsaadah Abd-Rahman、Yew Beng Kang、Mallikarjuna Rao Pichika

  DOI：10.1016/j.ejmech.2014.03.002

  日期：2014.4

  In the present study, a series of 46 chalcones were synthesised and evaluated for antiproliferative activities against the human TRAIL-resistant breast (MCF-7, MDA-MB-231), cervical (HeLa), ovarian (Caov-3), lung (A549), liver (HepG2), colorectal (HT-29), nasopharyngeal (CNE-1), erythromyeloblastoid (K-562) and T-Iymphoblastoid (CEM-SS) cancer cells. The chalcone 38 containing an amino (-NH2) group on ring A was the most potent and selective against cancer cells. The effects of the chalcone 38 on regulation of 43 apoptosis-related markers in HT-29 cells were determined. The results showed that 20 apoptotic markers (Bad, Bax, BcI-2, Bcl-w, Bid, Bim, CD40, Fas, HSP27, IGF-1, IGFBP-4, IGFBP-5, Livin, p21, Survivin, 5TNE-R2, TRAIL-R2, XIAP, caspase-3 and caspase-8) were either up regulated or down regulated. (C) 2014 Elsevier Masson SAS.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.
• Trisulfur-Radical-Anion-Triggered C(sp²)–H Amination of Electron-Deficient Alkenes
  作者：Khang X. Nguyen、Phuc H. Pham、Thao T. Nguyen、Chou-Hsun Yang、Hoai T. B. Pham、Tung T. Nguyen、Haobin Wang、Nam T. S. Phan

  DOI：10.1021/acs.orglett.0c03846

  日期：2020.12.18

  A trisulfur-radical-anion (S3̇–)-triggered C(sp2)–H amination of α,β-unsaturated carbonyl derivatives with simple amines has been demonstrated. This protocol provides convenient access to a variety of synthetically valuable N-unprotected and secondary β-enaminones with absolute Z selectivity and tertiary β-enaminones with E selectivity. Mechanistic probe and electronic structure theory calculations

  甲trisulfur自由基-阴离子（š 3＆CenterDot; -）-triggered C（SP 2）-H的α胺化，用简单的胺β不饱和羰基衍生物已被证明。该方案可方便地获得具有绝对Z选择性的多种合成有价值的N-未保护和仲β-烯胺酮，以及具有E选择性的叔β-烯胺酮。机械探针和电子结构理论计算表明该S 3＆CenterDot; -发起经由硫杂丙环亲核攻击中间。
• 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。