3-(4-cyanobenzylidene)flavanone | 77015-49-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-(4-cyanobenzylidene)flavanone
• 英文别名: 4-[(E)-(4-oxo-2-phenylchromen-3-ylidene)methyl]benzonitrile
• CAS: 77015-49-7
• 化学式: C₂₃H₁₅NO₂
• 分子量: 337.378
• InChiKey: PCQOQBMCMJDSIF-ZHZULCJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-cyanobenzylidene)flavanone 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 552.0h， 以80%的产率得到trans,trans-(+/-)-3'-(4-Cyanophenyl)-2-phenylspiro-4-one
  参考文献：
  名称：

  Dioxirane Oxidation of 3-Arylideneflavanones: Diastereoselective Formation of trans,trans Spiroepoxides from the E Isomers

  摘要：

  Oxidation of the E isomers of the 3-arylideneflavanones 1 by dimethyldioxirane in acetone solution at ambient temperature led to spiroepoxides trans,trans-2 in high yields (greater than or equal to 170%) and complete diastereoselectivity. Steric interaction with the axial aryl group in the 3-arylideneflavanone E-1. directs the attack of the dioxirane to the opposite side during the oxygen transfer to afford exclusively the trans,trans-2 epoxides, which clearly demonstrates the advantage of dimethyldioxirane as oxidant. In comparison, these substrates give under Weitz-Scheffer conditions (alkaline hydrogen peroxide) both diastereomeric epoxides (dr ca. 3:1) in poor yields (less than or equal to 130%), while m-CPBA produces trans,trans-2 spiroepoxides preferentially, but also in low yields (less than or equal to 140%).(1,2) Attempted epoxidation of the Z isomers afforded instead the 3-benzoylflavones 3 and/or 3-benzoylflavanones 4 in low yields. With the much more reactive methyl(trifluoromethyl)dioxirane, the E-1 isomers also gave the trans,-trans-2 spiroepoxides diastereoselectively in high yields, but the Z isomers suffered complete decomposition. Presumably the sterically hindered Z isomers encumber the oxygen atom transfer by the dioxirane and radical-type oxidation dominates for these reluctant substrates.

  DOI：

  10.1021/jo00083a035
• 作为产物：
  描述：

  4-氰基苯甲醛 、 黄烷酮 在 哌啶 作用下， 生成 3-(4-cyanobenzylidene)flavanone
  参考文献：
  名称：

  Pijewska; Kamecki; Perka-Karolczak, Pharmazie, 1993, vol. 48, # 4, p. 254 - 257

  摘要：

  DOI：

文献信息

• Facile Synthesis of Tetrazolylchromonoids and Related Compounds
  作者：Tamás Patonay、Albert Lévai

  DOI：10.1002/ardp.19943270310

  日期：——

  The reaction between the appropriate nitriles and tributyltin azide (TBTA) provides an easy and efficient method for the synthesis of the title compounds. Treatment of thiocyanate 9b with TBTA affords the alkylthio‐substituted tetrazole 10b.

  合适的腈与叠氮化三丁基锡 (TBTA) 之间的反应为合成标题化合物提供了一种简单有效的方法。用 TBTA 处理硫氰酸酯 9b 得到烷硫基取代的四唑 10b。