1,2,3,3-tetraphenylprop-2-en-1-one | 6333-11-5

• 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: 1,2,3,3-tetraphenylprop-2-en-1-one
• 英文别名: 1,2,3,3-tetdrahenylprop-2-en-1-one；1,2,3,3-tetraphenyl-2-propen-1-one；tetraphenyl-propenone；Tetraphenyl-propenon；α.β-Diphenyl-chalkon；γ-Oxo-α.α.β.γ-tetraphenyl-α-propylen
• CAS: 6333-11-5
• 化学式: C₂₇H₂₀O
• 分子量: 360.455
• InChiKey: LJVKAAJFUJOCEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• 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：

  1,2,3,3-tetraphenylprop-2-en-1-one 在 硫酸 、 溶剂黄146 、 苯 作用下， 生成 1-methyl-1,2,3-triphenyl-1H-indene
  参考文献：
  名称：

  THE PREPARATION OF SOME CHLOROMETHYLINDENES AND THE DETERMINATION OF THEIR REACTIVITIES TOWARDS SODIUM IODIDE¹

  摘要：

  DOI：

  10.1021/jo01204a014
• 作为产物：
  描述：

  (1Z)-2-偶氮基-3-氧代-1,3-二苯基-1-丙烯-1-醇 在 tris(triphenylphosphine)ruthenium(II) chloride 、 四(三苯基膦)钯 、 草酰氯 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 35.0h， 生成 1,2,3,3-tetraphenylprop-2-en-1-one
  参考文献：
  名称：

  钌（II）催化的重氮二羰基化合物制备各种α，β-和β，β-二卤代烯酮的方案

  摘要：

  AbstractEfficient one‐step syntheses of α,β‐ and β,β‐dihaloenones were achieved by ruthenium(II)‐catalyzed reactions between cyclic or acyclic diazodicarbonyl compounds and oxalyl chloride or oxalyl bromide in moderate to good yields. This methodology offers several significant advantages, which include ease of handling, mild reaction conditions, one‐step reaction, and the use of an effective and non‐toxic catalyst. The synthesized compounds were further transformed into highly functionalized novel molecules bearing aromatic rings on the enone moiety using the Suzuki reaction.magnified image

  DOI：

  10.1002/adsc.201400348

文献信息

• Hypervalent Iodine Oxidation of Allenes: Synthesis of 3-Acetoxy-3-alkoxypropynes, 2-Alkoxy-3-tosyloxypropanals and Phenyl-Substituted Propenals and Propenones
  作者：Robert M. Moriarty、Thomas E. Hopkins、Radhe K. Vaid、Beena K. Vaid、Stuart G. Levy

  DOI：10.1055/s-1992-26244

  日期：——

  1-Alkoxyallenes yield 3-acetoxy-3-alkoxypropynes upon oxidation with [(diacetoxy)iodo]benzene at - 78°C in dichloromethane. Treatment with [hydroxy(tosyloxy)iodo]benzene under similar conditions gives 2-alkoxy-3-tosyloxypropanals. Phenyl-substituted propenals and propen-1-ones are obtained from the treatment of phenyl-substituted alienes with [hydroxy(tosyloxy)iodo]benzene in dichloromethane at - 78°C.

  中文翻译结果：1-烷氧基丙二烯在-78°C下用二氯甲烷中的[双乙酰氧基碘]苯氧化生成3-乙酰氧基-3-烷氧基丙炔。在相似条件下，使用[羟基(甲苯磺酰氧基)碘]苯处理得到2-烷氧基-3-甲苯磺酰氧基丙醛。在-78°C下，用二氯甲烷中的[羟基(甲苯磺酰氧基)碘]苯处理苯基取代的丙二烯，生成苯基取代的丙烯醛和丙烯-1-酮。
• The Action of Lithium Aluminum Hydride and Phenyllithium on Phenylated Chalcones¹
  作者：Robert E. Lutz、Everett H. Rinker

  DOI：10.1021/ja01607a039

  日期：1955.1

  Abstract : Aluminum isopropoxide in normal fashion reduces the carbonyl of trans- but not of cis-alpha-phenylchalcone; lithium aluminum hydride reduces the carbonyls of both, and also the carbonyl of alpha, beta-diphenylchalcone. Phenyllithium adds 48% 1,2 and 33% 1,4 to the trans isomer but chiefly 1,4 to the cis; and it adds only 1,2 to the carbonyl of alpha-beta-diphenylchalcone. These results are

  摘要: 异丙醇铝以正常方式还原反式-α-苯基查尔酮的羰基，但不还原顺式-α-苯基查尔酮的羰基；氢化铝锂还原两者的羰基，也还原 α, β-二苯基查尔酮的羰基。苯基锂向反式异构体添加 48% 1,2 和 33% 1,4，但主要向顺式异构体添加 1,4；它仅在 α-β-二苯基查尔酮的羰基上增加 1,2。这些结果显示符合一致的模式。（作者）
• Photochemical and thermal transformations of 2(3H)-furanones and bis(benzofuranones). A laser flash photolysis study
  作者：B. B. Lohray、C. V. Kumar、P. K. Das、M. V. George

  DOI：10.1021/ja00336a010

  日期：1984.11

  Photochemical and thermal transformations of a few 2(3H)-furanones and bis(benzofuranones) were investigated in detail. Laser flash photolysis technique was employed for the first time to examine the mechanistic aspects of these photochemical reactions. Spectral and kinetic data are presented for the triplets of 2(3H)-furanones containing styrene and cis-stilbene moieties constrained into planar geometries

  详细研究了一些 2(3H)-呋喃酮和双 (苯并呋喃酮) 的光化学和热转变。首次采用激光闪光光解技术来检查这些光化学反应的机械方面。提供了 2(3H)-呋喃酮三联体的光谱和动力学数据，其中包含限制在平面几何形状中的苯乙烯和顺二苯乙烯部分。呋喃酮的光解在苯或甲醇溶液中进行。
• Effects of strong π-electron accepting substituents on structure preference for thiocarbonyl ylide or thiirane
  作者：Kitaro Oka、Akira Dobashi、Shoji Hara

  DOI：10.1016/0040-4039(80)80240-1

  日期：1980.1

  Equilibrium between thiocarbonyl ylide and thiirane depends upon the π-electron accepting nature of the substituents. Four carbonyl and ester groups move the equilibrium far to the thiocarbonyl ylide side.

  硫代羰基内酯和硫杂环丁烷之间的平衡取决于取代基的π电子接受性质。四个羰基和酯基将平衡点移至硫代羰基内酯一侧。
• Sequential multiple-photon photochemistry of sterically congested enones
  作者：Karlyn A. Schnapp、Philip L. Motz、Sharon M. Stoeckel、R.Marshall Wilson、Jeanette A. Krause Bauer、Cornelia Bohne

  DOI：10.1016/0040-4039(96)00284-5

  日期：1996.4

  The photochemistry of sterically hindered enones 1 and 2 is described. A novel photorearrangement occurs in both systems which involves carbonyl attack on the adjacent phenyl ring, expansion of that ring to a cycloheptatriene and subsequent photochemically induced 1,7-phenyl migration.

  描述了位阻烯酮1和2的光化学。在两个系统中均发生新的光重排，这涉及羰基对相邻苯环的攻击，该环向环庚三烯的扩展以及随后的光化学诱导的1,7-苯基迁移。