(Z)-3-phenyl-2-(phenylselanyl)acrylaldehyde | 91890-50-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (Z)-3-phenyl-2-(phenylselanyl)acrylaldehyde
• 英文别名: (Z)-3-phenyl-2-(phenylselenyl)acrylaldehyde；(Z)-2-phenylseleno-3-phenyl-2-propen-1-al；(Z)-3-phenyl-2-phenylselanylprop-2-enal
• CAS: 91890-50-5
• 化学式: C₁₅H₁₂OSe
• 分子量: 287.22
• InChiKey: MXPGBFXLSWHYET-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• 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：

  (Z)-3-phenyl-2-(phenylselanyl)acrylaldehyde 在 双氧水 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 dihydro-2,5 phenyl-5 phenylseleno-4 furannecarboxylate d'ethyle-2
  参考文献：
  名称：

  Synthese D′α-hydroxyallenes α-fonctionnalises a partir D′α-phenylselenoenals

  摘要：

  DOI：

  10.1016/s0040-4039(01)90093-0
• 作为产物：
  描述：

  [(Z)-3,3-diethoxy-1-phenylprop-1-en-2-yl]selanylbenzene 在 三氟甲磺酸三甲基硅酯 、 乙烯基三甲基硅烷 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到(Z)-3-phenyl-2-(phenylselanyl)acrylaldehyde
  参考文献：
  名称：

  A New 1-Alkoxy-2-(chalcogeno)allylic or 1-Alkoxy-2,4-bis(chalcogeno)penta-2,4-dienyl Cation:  Highly-Regioselective Allylating or Penta-2,4-dienylating Electrophiles and Their Reactions

  摘要：

  2-(Chalcogeno)-1-ethoxyallylic cations 4A are easily generated from the reactions of 2-(chalcogeno)-1-ethoxyprop-1-en-3-ols 2a-e or 2-(chalcogeno)prop-2-enal acetals 3a-c and TMSOTf and reacted with various nucleophiles to give the adducts 5a-8a, 5b-11b, and 5c-e regio and stereoselectively. 2,4-Bis(chalcogeno)penta-2,4-dienal acetals 16a,c and the 2,4,6-tris(phenylthio)hepta-2,4,6-trienal acetal 20c also gave the dienones 17a,c and 21c in good yields. Furthermore, the intramolecular cyclization of the alkenyl alcohols 25a,b and the 2,4-dienal 2,4-dinitrophenyl hydrazones 29a-c afforded the tetrahydrofurans 26a,b and 3,5-bis(chalcogeno)pyridines 30a-c, respectively.

  DOI：

  10.1021/jo9807767

文献信息

• New synthesis and cyclopropanation of α-phenylselanyl α,β-unsaturated ketones with non-stabilized phosphorus ylides
  作者：Sébastien Redon、Stéphane Leleu、Xavier Pannecoucke、Xavier Franck、Francis Outurquin

  DOI：10.1016/j.tet.2008.07.025

  日期：2008.9

  A general method for the preparation of α-phenylselanyl enones is described. Phosphorus ylides react with these α-phenylselanyl enones in a 1,4-addition, leading to cyclopropanes and/or dihydrofurans, depending on the substitution pattern. This unusual reactivity is due to the phenylselanyl moiety, hindering the carbonyl of the enone and making it less prone to 1,2-additions or promoting conjugate

  描述了制备α-苯基硒基烯酮的一般方法。磷取代基与这些α-苯基硒基烯酮以1,4-加成反应，生成环丙烷和/或二氢呋喃，具体取决于取代方式。这种不寻常的反应性是由于苯硒基部分造成的，它阻碍了烯酮的羰基，使其更不容易通过电子作用加成1，2-加成或促进共轭加成。
• Meyer–Schuster-Type Rearrangement of Propargylic Alcohols into α-Selenoenals and -enones with Diselenides
  作者：Yong-Liang Ban、Long You、Kai-Wen Feng、Fei-Cen Ma、Xiao-Ling Jin、Qiang Liu

  DOI：10.1021/acs.joc.1c00167

  日期：2021.4.2

  preparation of a diverse array of multisubstituted α-selenoenals and -enones from readily accessible propargylic alcohols and diselenides. The transformation proceeds via the Selectfluor-promoted selenirenium pathway, which enables selenenylation/rearrangement of a variety of propargylic alcohols. Gram-scale experiments showed the potential of this synergistic protocol for practical application.

  我们描述了一种温和且广泛适用的方案，用于从易于获得的炔丙醇和二硒化物制备多种多样的多取代的α-硒烯醛和-烯酮阵列。转化通过Selectfluor促进的硒鎓途径进行，该途径可实现各种炔丙醇的硒烯基化/重排。克级实验显示了这种协同协议在实际应用中的潜力。
• Visible-light-induced phenylchalcogenyl-oxygenation of allenes having aryl or electron withdrawing substituents with ambient air as a sole oxidant
  作者：Gullapalli Kumaraswamy、Swargam Vijaykumar、Kukkadapu Ankamma、Vykunthapu Narayanarao

  DOI：10.1039/c6ob02033j

  日期：——

  The synthesis of regio- and stereoselective aryl substituted α,β-unsaturated aldehydes and ketones from activated allenes was achieved. This mild and non-metallic oxidation is exclusively driven by benign ambient air and triggered by visible light. The same starting materials under ideal anaerobic conditions led to the 2,3-diphenylselenation adduct with no trace of oxygenated products, demonstrating

  从活化的烯上合成了区域和立体选择性的芳基取代的α，β-不饱和醛和酮。这种温和的非金属氧化仅由良性环境空气驱动，并由可见光触发。在理想的厌氧条件下，相同的原料导致形成2,3-二苯硒化加合物，而没有痕量的氧化产物，这表明溶解氧是两个不同反应路径的化学开关。该协议的显着特征是通过辐照两个有机分子之一实现的单电子转移（SET），从而避免了敏化剂形成自由基离子对。
• Selenylated dienes: synthesis, stereochemical studies by 77Se NMR, and transformation into functionalized allenes
  作者：Sebastien Redon、Anne-Lise Berthe Berkaoui、Xavier Pannecoucke、Francis Outurquin

  DOI：10.1016/j.tet.2007.02.082

  日期：2007.4

  some cases. In THF, [2,3]-sigmatropic rearrangement of allylic selenoxides, selenimides, and dihalo-selenuranes occurred, yielding allenyl alcohols 12–15, allenyl carbamates 16c–19c, and 1-haloalkyl allenes 20c–22c, respectively.

  2- Phenylselanyl-1,3-二烯3 - 8通过从α-phenylselanylα，β不饱和醛开始维悌希或维悌希-霍纳-埃蒙斯程序制备。通过77 Se和1 H NMR确定每种二烯异构体的比率和构型。然后将这些二烯氧化为亚硒酸盐，在某些情况下可以分离出来。在THF中，[2,3]烯丙基selenoxides，selenimides，和二卤代selenuranes的-sigmatropic重排发生，得到丙二烯基醇12 - 15，丙二烯基氨基甲酸酯16C - 19C，和1-卤代丙二烯20C - 22C，分别。
• The First Example of the 1-Chalcogene-Substituted Formylolefination of the Ketones and Aldehydes Using 1-Lithio-2-ethoxyvinyl Chalcogenides
  作者：Mitsuhiro Yoshimatsu、Kiyomi Oguri、Kazunari Ikeda、Satoshi Gotoh

  DOI：10.1021/jo980487i

  日期：1998.6.1

  The alpha-chalcogene-substituted formylolefinations of ketones and aldehydes proceeded using 1-lithio-2-ethoxyvinyl chalcogenides/PPSE or TMSOTf produce the alpha-chalcogenoformylolefinated products 4a-1 in high yields. Tandem-formylolefination provided the (2Z,4Z)-2,4-bis(chalcogeno)pent-2,4-dienals 5d,h,i and (2Z,4Z,6Z)-2,4,6-tris(phenylthio)hept-2, derivatives 7d and 8d, respectively.