(E)-1-Hydroxy-1,4-diphenyl-but-3-en-2-one | 121078-41-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-Hydroxy-1,4-diphenyl-but-3-en-2-one
• 英文别名: (E)-1-hydroxy-1,4-diphenylbut-3-en-2-one
• CAS: 121078-41-9
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: PXONVVFXPIXXKX-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Phenyl-[2-((E)-styryl)-[1,3]dithian-2-yl]-methanol 在 水 、 mercury dichloride 作用下， 生成 (E)-1-Hydroxy-1,4-diphenyl-but-3-en-2-one
  参考文献：
  名称：

  二硫代肉桂酸锂与羰基化合物的反应：HSAB原理的测试

  摘要：

  通过介导BF 3 .Et 2 O，二硫取代的肉桂基锂2主要在α位与羰基化合物反应。当在不存在BF 3 .Et 2 O的情况下进行反应时，没有发现选择性。

  DOI：

  10.1016/s0040-4039(00)82231-5

文献信息

• 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.
• Acylzirconocene Chloride as an “Unmasked” Acyl Anion
  作者：Susumu Harada、Takeo Taguchi、Nobuhito Tabuchi、Kensuke Narita、Yuji Hanzawa

  DOI：10.1002/(sici)1521-3773(19980703)37:12<1696::aid-anie1696>3.0.co;2-p

  日期：1998.7.3

  Under mild conditions the acyl group of acylzirconocene chloride 1 formed from an alkene or alkyne and [(C5 H5 )2 ZrHCl] reacts as an "unmasked" acyl anion. The Lewis acid mediated reactions with aldehydes that yield α-ketol products in high yields demonstrate the versatility of this reagent for C-C coupling.
• Reaction of dithio-substituted cinnamyllithium with carbonyl compounds: a test of the HSAB principle
  作者：Jim-Min Fang、Ming-Yi Chen、Wen-Jin Yang

  DOI：10.1016/s0040-4039(00)82231-5

  日期：1988.1

  By mediation of BF3.Et2O, dithio-substituted cinnamyllithium 2 reacted predominantly at the α-site with carbonyl compounds. No selectivity was found when the reaction was performed in the absence of BF3.Et2O.

  通过介导BF 3 .Et 2 O，二硫取代的肉桂基锂2主要在α位与羰基化合物反应。当在不存在BF 3 .Et 2 O的情况下进行反应时，没有发现选择性。