(E)-1-(4-nitrophenyl)-4-phenylbut-3-en-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(4-nitrophenyl)-4-phenylbut-3-en-2-one
• 英文别名: 1-(4-nitro-phenyl)-4-phenyl-but-3-en-2-one；α-(4-Nitro-phenyl)-α'-benzyliden-aceton；1-(4-Nitro-phenyl)-4-phenyl-but-3-en-2-on；(4-Nitro-benzyl)-styryl-keton
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: QRYBHOHJRHPIAU-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 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：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对硝基苯酚 在 吡啶 、 palladium diacetate 、 三正丁基氟化锡 、 cesium fluoride 、 lithium chloride 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 (E)-1-(4-nitrophenyl)-4-phenylbut-3-en-2-one
  参考文献：
  名称：

  Regioselectivity Switch Achieved in the Palladium Catalyzed α-Arylation of Enones by Employing the Modified Kuwajima–Urabe Conditions

  摘要：

  A new regioselective approach to the synthesis of alpha-aryl enones is reported. This represents an important application of the Kuwajima-Urabe protocol toward the synthesis of this simple albeit complex functional array. Several a-aryl enones were synthesized by the palladium catalyzed arylation of triethylsilylenol ethers of enones with high regioselectivity and broad scope, utilizing sterically encumbered electron-rich phosphine ligands to drive the reaction.

  DOI：

  10.1021/ol300401c

文献信息

• Cyclic α-Alkoxyphosphonium Salts from (2-(Diphenylphosphino)phenyl)methanol and Aldehydes and Their Application in Synthesis of Vinyl Ethers and Ketones via Wittig Olefination
  作者：Wenhua Huang、Hong-Ying Rong、Jie Xu

  DOI：10.1021/acs.joc.5b01031

  日期：2015.7.2

  synthesized from (2-(diphenylphosphino)phenyl)methanol and aldehydes in 36–89% yields. These phosphonium salts are bench-stable solids and undergo Wittig olefination with aldehydes under basic conditions (K2CO3 or t-BuOK) to form benzylic vinyl ethers, which are readily hydrolyzed to 1,2-disubstituted ethanones under acidic conditions. The formation mechanism of these phosphonium salts via hemiacetal

  环状α-烷氧基phosph盐是由（2-（二苯基膦基）苯基）甲醇和醛合成的，产率为36-89％。这些phospho盐是稳定的固体，并在碱性条件下（K 2 CO 3或叔丁基）与醛进行Wittig烯化反应，形成苄基乙烯基醚，该苄基乙烯基醚在酸性条件下容易水解为1,2-二取代的乙酮。还提出了这些phospho盐通过半缩醛的形成机理。
• Kleucker, Chemische Berichte, 1922, vol. 55, p. 1648
  作者：Kleucker

  DOI：——

  日期：——
• Regioselectivity Switch Achieved in the Palladium Catalyzed α-Arylation of Enones by Employing the Modified Kuwajima–Urabe Conditions
  作者：Ajit Prabhakar Kale、Govind Goroba Pawar、Manmohan Kapur

  DOI：10.1021/ol300401c

  日期：2012.4.6

  A new regioselective approach to the synthesis of alpha-aryl enones is reported. This represents an important application of the Kuwajima-Urabe protocol toward the synthesis of this simple albeit complex functional array. Several a-aryl enones were synthesized by the palladium catalyzed arylation of triethylsilylenol ethers of enones with high regioselectivity and broad scope, utilizing sterically encumbered electron-rich phosphine ligands to drive the reaction.