1-phenylhexa-2,4-dien-1-one | 74743-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenylhexa-2,4-dien-1-one
• 英文别名: 1-Phenyl-2,4-hexadien-1-one
• CAS: 74743-50-3
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: GHNBEBDYYSVNEK-UHFFFAOYSA-N

物化性质

• 沸点：
  276.6±13.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  1-phenylhexa-2,4-dien-1-one 在 sodium tetrahydroborate 、 1,10-菲罗啉 、 cerium(III) chloride heptahydrate 、 sodium t-butanolate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 4.25h， 生成 (E)-1-phenylhex-4-ene-1-one
  参考文献：
  名称：

  Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

  摘要：

  Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the S(RN)1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

  DOI：

  10.1021/acs.orglett.5b03124
• 作为产物：
  描述：

  1-benzoyl-2-chloroethene 以 水 为溶剂， 生成 1-phenylhexa-2,4-dien-1-one
  参考文献：
  名称：

  Cuvigny,T.; Normant,H., Bulletin de la Societe Chimique de France, 1960, p. 515 - 521

  摘要：

  DOI：

文献信息

• Ruthenium(<scp>ii</scp>)-catalyzed regioselective 1,6-conjugate addition of umpolung aldehydes as carbanion equivalents
  作者：Hyotaik Kang、Chao-Jun Li

  DOI：10.1039/d1sc03732c

  日期：——

  addition of carbon nucleophiles to electron-deficient ketones. Yet, 1,6-conjugate additions of extended conjugated systems largely remain underexplored due to difficulties in controlling the regioselectivity. Herein, we report umpolung aldehydes as carbanion equivalents for highly regioselective 1,6-conjugate addition reactions to unsaturated ketones, with preliminary studies of the enantioselective variant

  构建 C-C 键的最有效和最可靠的方法之一涉及将碳亲核试剂共轭加成到缺电子酮上。然而，由于难以控制区域选择性，扩展共轭体系的 1,6-共轭添加在很大程度上仍未得到充分探索。在这里，我们报告了 umpolung 醛作为碳负离子等价物，用于对不饱和酮进行高度区域选择性的 1,6-共轭加成反应，并对对映选择性变体进行了初步研究。钌( II )催化剂和富电子二齿膦配体的协同作用对于温和反应条件下的反应性和选择性至关重要。
• Ruthenium-Catalyzed Transformation of 3-Benzyl But-1-ynyl Ethers into 1,3-Dienes and Benzaldehyde via Transfer Hydrogen
  作者：Kuo-Liang Yeh、Bo Liu、Yen-Ting Lai、Chia-Wen Li、Rai-Shung Liu

  DOI：10.1021/jo049514x

  日期：2004.7.1

  TpRuPPh3(CH3CN)2PF6 catalyzed the transformation of various 3-benzyl but-1-ynyl ethers into dienes and benzaldehyde at a catalyst loading of 5 mol %. This process represents an atypical pattern of transfer hydrogenation. This catalytic reaction can be applied to various derivatives of 2-ethynyl tetrahydrofurans and pyrans to cleave their ether rings and gives diene and tethered aldehyde functionalities

  TpRuPPh 3（CH 3 CN）2 PF 6以5mol％的催化剂负载量催化了各种3-苄基丁-1-炔基醚向二烯和苯甲醛的转化。该过程代表转移氢化的非典型模式。该催化反应可用于2-乙炔基四氢呋喃和吡喃的各种衍生物，以裂解它们的醚环并分别得到二烯和束缚的醛官能团。
• Unique site-selectivity control in asymmetric Michael addition of azlactone to alkenyl dienyl ketones enabled by P-spiro chiral iminophosphorane catalysis
  作者：Ken Yoshioka、Kohei Yamada、Daisuke Uraguchi、Takashi Ooi

  DOI：10.1039/c7cc01715d

  日期：——

  and enantioselective 1,6-addition of azlactone to various alkenyl dienyl ketones has been achieved under P-spiro chiral triaminoiminophosphorane catalysis. This site-selectivity control relies on the distinct ability of the conjugate acids of iminophosphoranes, aminophosphonium ions, to precisely differentiate between the three electrophilic reaction sites of alkenyl dienyl ketones, which is further demonstrated

  在P-螺环手性三氨基亚氨基正膦催化下，将内酯向多种烯基二烯基酮进行高度区域，非对映和对映选择性的1,6-加成反应。这种位点选择性控制依赖于亚氨基正膦酸酯，氨基离子的共轭酸在烯基二烯基酮的三个亲电反应位点之间精确区分的独特能力，这进一步通过区分性不对称的1，6-添加add内酯来证明。二烯基酮，保留完整存在的烯基酮。
• Iridium-catalyzed Annulation of α,β-Unsaturated Amides with Electron-deficient Conjugated Dienes
  作者：Kotone Murakami、Midori Nagamoto、Takahiro Nishimura

  DOI：10.1246/cl.200193

  日期：2020.6.5

  Annulation of α,β-unsaturated amides with electron-deficient 1,3-dienes gave 5,6-dihydropyridin-2(1H)-ones in the presence of a hydroxoiridium catalyst. The reaction proceeded via direct C–H alkyla...

  在羟基铱催化剂存在下，α,β-不饱和酰胺与缺电子的 1,3-二烯环化得到 5,6-二氢吡啶-2(1H)-酮。反应通过直接的C-H烷基化进行...
• Trienamine Catalysis with 2,4-Dienones: Development and Application in Asymmetric Diels-Alder Reactions
  作者：Xiao-Feng Xiong、Quan Zhou、Jing Gu、Lin Dong、Tian-Yu Liu、Ying-Chun Chen

  DOI：10.1002/anie.201200248

  日期：2012.4.27

  A tri‐ing reaction: An asymmetric Diels–Alder cycloaddition of δ,δ‐disubstituted 2,4‐dienones is possible through the trienamine catalysis of cinchona‐based primary amines (see scheme). An array of electron‐deficient dienophiles, such as N‐substituted maleimides and 3‐alkenyl oxindoles, were tolerated, and multifunctional cyclohexene derivatives were obtained in excellent stereoselectivity and with

  Triing反应：δ，δ-二取代的2,4-二壬烯的不对称Diels-Alder环加成反应可能是通过基于金鸡纳酮的伯胺的三烯胺催化而实现的（参见方案）。可以耐受一系列缺电子的亲二烯体，例如N-取代的马来酰亚胺和3-烯基氧吲哚，并以优异的立体选择性和高非对映异构体比率获得了多功能环己烯衍生物。