5-Phenyl-1--pentadien-(2,4)-on-(1) | 100001-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Phenyl-1--pentadien-(2,4)-on-(1)
• 英文别名: 5-Phenyl-1--1-oxo-pentadien-(2,4)；5-Phenyl-1-(naphthyl-(2))-1-oxo-pentadien-(2,4)；1-(2-Naphthyl)-5-phenyl-2,4-pentadiene-1-one；1-naphthalen-2-yl-5-phenylpenta-2,4-dien-1-one
• CAS: 100001-81-8
• 化学式: C₂₁H₁₆O
• 分子量: 284.357
• InChiKey: KPPOVOMNCMSREF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Phenyl-1--pentadien-(2,4)-on-(1) 在 甲酸铵 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以68%的产率得到2-(naphthalen-2-yl)-6-phenylpyridine
  参考文献：
  名称：

  线性的α，β，γ，δ-不饱和酮通过加成铵和随后的环化反应合成不对称的2,6-二芳基吡啶

  摘要：

  纪念张永民教授（1932-2019） 抽象的 建立了一种简单有效的方法，通过在空气气氛下用甲酸铵将α，β，γ，δ-不饱和酮环化来合成不对称的2,6-二芳基吡啶。该反应是无金属的，并且易于获得的起始原料在操作上是方便的。已经提出了33个例子，其中大多数显示出良好的产量。 建立了一种简单有效的方法，通过在空气气氛下用甲酸铵将α，β，γ，δ-不饱和酮环化来合成不对称的2,6-二芳基吡啶。该反应是无金属的，并且易于获得的起始原料在操作上是方便的。已经提出了33个例子，其中大多数显示出良好的产量。

  DOI：

  10.1055/s-0037-1610725
• 作为产物：
  描述：

  反式肉桂醛 、 2-萘乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 5-Phenyl-1--pentadien-(2,4)-on-(1)
  参考文献：
  名称：

  通过硼酸与线性 α,β,γ,δ-不饱和酮的不对称 1,4-加成反应，高度区域选择性地引入芳基取代基

  摘要：

  使用磷钯环催化剂开发了一种有效的钯 (II) 催化的区域选择性不对称 1,4-共轭加成芳基硼酸到线性 α,β,γ,δ-不饱和酮。以完美的区域选择性、可观的产率和对映选择性专门获得了相关的 1,4-产物。在室温下进行的该协议中可以容忍多种二烯酮底物以及取代的芳基硼酸。

  DOI：

  10.1055/s-0035-1560513

文献信息

• Synthesis of 7-arylethyl-5-arylpyrazolo $$[1{,}5\hbox {-}a]$$ [ 1 , 5 - a ] pyrimidines through an aza-Michael addition/nucleophilic addition/1,3-hydrogen transfer cascade
  作者：Zheng Li、Demeng Xie、Jiaojiao He、Yan Du、Jingya Yang

  DOI：10.1007/s12039-017-1365-4

  日期：2017.10

  AbstractAn efficient method for the synthesis of pyrazolo\([1,}5\hbox -}a]\)pyrimidines by the tandem reactions of dienones with pyrazole-3-amine through an aza-Michael addition/nucleophilic addition/1,3-hydrogen transfer process in the presence of potassium hydroxide is described. This protocol offers access to 7-arylethyl-5-arylpyrazolo\([1,}5\hbox -}a]\)pyrimidines in good to excellent yield

  摘要一种通过二氮酮与吡唑-3-胺通过aza-Michael加成/亲核加成/ 1串联反应合成吡唑并\（[[1 ，} 5 \ hbox -} a] \）嘧啶的有效方法，描述了在氢氧化钾存在下的3-氢转移过程。该方案可以良好的收率获得7-芳基乙基-5-芳基吡唑并（[[1 ，} 5 \ hbox -} a] \）嘧啶。同时，对于4-取代的二烯酮，通过氮杂-迈克尔加成/亲核加成/氧化过程得到不同的产物7-芳基乙烯-5-芳基吡唑并（[1 ，} 5 \ hbox -} a] \）嘧啶。已经进行了克规模的反应，以证明用于放大过程的优化程序的效力。 图形概要 概要通过4-未取代的二烯酮与吡唑-3-胺的反应有效地合成了7-芳基乙基-5-芳基吡唑并（[[1 ，} 5 \ hbox -} a] \）嘧啶。相反，通过4-取代的二烯酮与吡唑-3-胺的反应可得到7-芳基乙烯-5-芳基吡唑并（[[1 ，}
• Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones
  作者：Kunal Nepali、Kanika Kadian、Ritu Ojha、Rajni Dhiman、Atul Garg、Gagandip Singh、Abhishek Buddhiraja、Preet Mohinder Singh Bedi、Kanaya Lal Dhar

  DOI：10.1007/s00044-011-9824-9

  日期：2012.10

  Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C-6-C-3-C-6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines.All the synthesized compounds were evaluated for in vitro cytotoxicity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Compound 68 was found to be the most potent showing broad spectrum of cytotoxicity against all the cell lines .
• Asymmetric 1,4-Conjugate Addition of Diarylphosphines to α,β,γ,δ-Unsaturated Ketones Catalyzed by Transition-Metal Pincer Complexes
  作者：Xiang-Yuan Yang、Wee Shan Tay、Yongxin Li、Sumod A. Pullarkat、Pak-Hing Leung

  DOI：10.1021/acs.organomet.5b00787

  日期：2015.10.26

  An enantioselective asymmetric 1,4-addition of diarylphosphines to linear alpha,beta,gamma,delta-unsaturated dienones was developed. A series of chiral PCP- and PCN-transition-metal (Pd, Pt and Ni) pincers, themselves prepared catalytically via asymmetric hydrophosphination, were sequentially screened to reveal the roles of backbone architecture and metal ion in catalyst design. The selected ester-functionalized PCP-palladium pincer afforded the chiral 1,4-phosphine adducts in excellent yields with up to >99% ee. The same catalyst when utilized for the hydrophosphination of an alpha,beta,gamma,delta-unsaturated malonate ester also revealed the critical role played by the ester functionality on the ligand backbone in dictating the enantioselectivity of the 1,6-adduct.
• Highly Regioselective Introduction of Aryl Substituents via Asymmetric 1,4-Addition of Boronic Acids to Linear α,β,γ,δ-Unsaturated Ketones
  作者：Sumod Pullarkat、Kennard Gan、Jia Ng、Abdul Sadeer

  DOI：10.1055/s-0035-1560513

  日期：——

  An efficient palladium(II)-catalyzed regioselective asymmetric 1,4-conjugate addition of arylboronic acids to linear α,β,γ,δ-unsaturated ketones is developed using phosphapalladacycle catalysts. The relevant 1,4-products were obtained exclusively with perfect regioselectivity, appreciable yields, and enantioselectivities. A wide range of dienone substrates as well as substituted arylboronic acids are

  使用磷钯环催化剂开发了一种有效的钯 (II) 催化的区域选择性不对称 1,4-共轭加成芳基硼酸到线性 α,β,γ,δ-不饱和酮。以完美的区域选择性、可观的产率和对映选择性专门获得了相关的 1,4-产物。在室温下进行的该协议中可以容忍多种二烯酮底物以及取代的芳基硼酸。
• Synthesis of Asymmetrical 2,6-Diarylpyridines from Linear α,β,γ,δ-Unsaturated Ketones by Addition of Ammonium Formate Followed by Annulation
  作者：Yejun Gao、Rener Chen、Yongmin Ma

  DOI：10.1055/s-0037-1610725

  日期：2019.10

  established for the synthesis of asymmetrical 2,6-diarylpyridines by cyclization of α,β,γ,δ-unsaturated ketones with ammonium formate under air atmosphere. The reaction is metal-free and operationally convenient from readily available starting materials. Thirty-three examples have been presented, most of which show good yields. A simple and efficient method has been established for the synthesis of asymmetrical

  纪念张永民教授（1932-2019） 抽象的 建立了一种简单有效的方法，通过在空气气氛下用甲酸铵将α，β，γ，δ-不饱和酮环化来合成不对称的2,6-二芳基吡啶。该反应是无金属的，并且易于获得的起始原料在操作上是方便的。已经提出了33个例子，其中大多数显示出良好的产量。 建立了一种简单有效的方法，通过在空气气氛下用甲酸铵将α，β，γ，δ-不饱和酮环化来合成不对称的2,6-二芳基吡啶。该反应是无金属的，并且易于获得的起始原料在操作上是方便的。已经提出了33个例子，其中大多数显示出良好的产量。