trans-1-phenyl-3-hepten-2-one | 129083-13-2

• 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: trans-1-phenyl-3-hepten-2-one
• 英文别名: (E)-1-phenylhept-3-en-2-one；(3E)-1-phenyl-3-hepten-2-one
• CAS: 129083-13-2
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: GAYZQQDRYGJFTP-BJMVGYQFSA-N

物化性质

• 沸点：
  76-79 °C(Press: 2 Torr)
• 密度：
  0.962±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-1-iodo-1-pentene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 一氧化碳 、 水 、 三乙胺 、 platinum(II) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.34h， 生成 trans-1-phenyl-3-hepten-2-one
  参考文献：
  名称：

  Regioselective hydrations of 1-aryl-3-en-1-ynes using gold and platinum catalysts: selective production of 2-en-1-ones and 3-en-1-ones

  摘要：

  区域控制的1-芳基-3-烯-1-炔的氢化反应已经通过使用IPrAuOTf和PtCl2/CO高效地实现了，生成了3-烯-1-酮和2-烯-1-酮；我们的实验数据显示催化剂的大小起着重要作用。

  DOI：

  10.1039/c4cc02786h

文献信息

• A Stereoselective and Practical Synthesis of (E)-α,β-Unsaturated Ketones from Aldehydes
  作者：Evita Balducci、Emanuele Attolino、Maurizio Taddei

  DOI：10.1002/ejoc.201001182

  日期：2011.1

  α,β-Unsaturated ketones can be prepared by reaction of differently substituted β-keto acids and aldehydes. The reaction is carried out under organocatalysis (β-alanine, 0.5 equiv.) and generates the enones with high E selectivity (>95 %). This version of the Verley–Doebner modification of the Knoevenagel reaction is a practical alternative to the classic Horner–Wadsworth–Emmons (HWE) reaction without

  α,β-不饱和酮可以通过不同取代的β-酮酸和醛反应制备。该反应在有机催化（β-丙氨酸，0.5 当量）下进行，并生成具有高 E 选择性（> 95 %）的烯酮。这个版本的 Knoevenagel 反应的 Verley-Doebner 修饰是经典 Horner-Wadsworth-Emmons (HWE) 反应的实用替代方案，不会形成高分子量副产物。该过程使用简单的试剂，可在符合原子经济原理的条件下应用于大规模合成。可以制备不同取代的脂肪族、芳香族或杂芳香族 α,β-不饱和酮。还描述了加氢甲酰化/Verley-Doebner Knoevenagel 伸缩过程的一个例子。
• A new synthesis of α,β-unsaturated ketones
  作者：J. Le Roux、M. Le Corre

  DOI：10.1016/0040-4039(90)80133-7

  日期：1990.1

  α,β-unsaturated ketones have been obtained by thermolysis of δ-hydroxy β-keto triphenylphosphoranes prepared from the corresponding β-keto phosphoranes.

  通过热解由相应的β-酮基膦烷制备的δ-羟基β-酮基三苯基正膦，可以得到α，β-不饱和酮。
• Benzotriazole- and 1,2,4-Triazole-Stabilized Allylic Anions:  Applications in Syntheses of Functionalized α,β-Unsaturated Ketones, γ-Lactones, γ-Lactams, and β-Substituted Esters
  作者：Alan R. Katritzky、Daming Feng、Hengyuan Lang

  DOI：10.1021/jo961396t

  日期：1997.2.1

  Deprotonated 1-(benzotriazol-1-yl)-1-ethoxy-2-hexene (7) reacted with alkyl halides, aldehydes, ketones, imines, and alpha-beta-unsaturated esters to give exclusively the alpha-alkylated products 8a-c, 10a,b, 12, 14, 16, and 18a,b, respectively. Without isolation, these products were hydrolyzed under mild conditions to generate the corresponding simple or functionalized alpha,beta-unsaturated ketones 9a-c, 11a,b, 13, 15, 17, and 19a,b. Similar reactions with the phenyl-substituted analog 3-(benzotriazol-1-yl)-3-ethoxy-1-phenyl-1-propene (21) also gave the analogous alpha-products, but they were accompanied by small amount of the gamma-products in most cases. By contrast, deprotonation of the corresponding triazole derivative 29 with butyllithium followed by reactions with alkyl halides, aldehydes, ketones, or imines yielded exclusively gamma-alkylated adducts 32, 34, 36, 38, 40, and 42. Intermediates 32, 34, 36, 38, 40, and 42 were readily converted into beta-substituted esters 33a-c, gamma-lactones 35a,b, 39, 41, and 43, and gamma-lactams 37a-c on hydrolysis.
• ROUX, J. LE;CORRE, M. LE, TETRAHEDRON LETT., 31,(1990) N8, C. 2591-2594
  作者：ROUX, J. LE、CORRE, M. LE

  DOI：——

  日期：——
• Regioselective hydrations of 1-aryl-3-en-1-ynes using gold and platinum catalysts: selective production of 2-en-1-ones and 3-en-1-ones
  作者：Bhanudas Dattatray Mokar、Rai-Shung Liu

  DOI：10.1039/c4cc02786h

  日期：——

  Regiocontrolled hydrations of 1-aryl-3-en-1-ynes have been accomplished with IPrAuOTf and PtCl2/CO to yield 3-en-1-ones and 2-en-1-ones efficiently; our experimental data indicates that the sizes of catalysts play an important role.

  区域控制的1-芳基-3-烯-1-炔的氢化反应已经通过使用IPrAuOTf和PtCl2/CO高效地实现了，生成了3-烯-1-酮和2-烯-1-酮；我们的实验数据显示催化剂的大小起着重要作用。