4-allyl-4'-(tert-butyl)-5,6-dihydro-[1,1'-bi(phenyl)]-3(4H)-one | 1415503-57-9

• 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: 4-allyl-4'-(tert-butyl)-5,6-dihydro-[1,1'-bi(phenyl)]-3(4H)-one
• 英文别名: 3-(4-Tert-butylphenyl)-6-prop-2-enylcyclohex-2-en-1-one；3-(4-tert-butylphenyl)-6-prop-2-enylcyclohex-2-en-1-one
• CAS: 1415503-57-9
• 化学式: C₁₉H₂₄O
• 分子量: 268.399
• InChiKey: OAMZBCGFNWDPLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  4-allyl-4'-(tert-butyl)-5,6-dihydro-[1,1'-bi(phenyl)]-3(4H)-one 、 氯乙酸酐 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以58%的产率得到4-allyl-4'-(tert-butyl)-5,6-dihydro-[1,1'-bi(phenyl)]-3-yl 2-chloroacetate
  参考文献：
  名称：

  Hydrolytic Enantioselective Protonation of Cyclic Dienyl Esters and a β-Diketone with Chiral Phase-Transfer Catalysts

  摘要：

  Hydrolytic enantioselective protonation of dienyl esters and a beta-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active alpha,beta-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).

  DOI：

  10.1021/ol3027363
• 作为产物：
  描述：

  4-allyl-4'-(tert-butyl)-5,6-dihydro-[1,1'-bi(phenyl)]-3-yl 2-chloroacetate 在 N-9-anthracenylmethylcinchonidinium chloride 、 potassium hydroxide 、 2-氯乙醇 作用下， 以 氯仿 、 均三甲苯 为溶剂， 反应 24.0h， 以92%的产率得到4-allyl-4'-(tert-butyl)-5,6-dihydro-[1,1'-bi(phenyl)]-3(4H)-one
  参考文献：
  名称：

  Hydrolytic Enantioselective Protonation of Cyclic Dienyl Esters and a β-Diketone with Chiral Phase-Transfer Catalysts

  摘要：

  Hydrolytic enantioselective protonation of dienyl esters and a beta-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active alpha,beta-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).

  DOI：

  10.1021/ol3027363

文献信息

• Hydrolytic Enantioselective Protonation of Cyclic Dienyl Esters and a β-Diketone with Chiral Phase-Transfer Catalysts
  作者：Eiji Yamamoto、Daichi Gokuden、Ayano Nagai、Takashi Kamachi、Kazunari Yoshizawa、Akiyuki Hamasaki、Tamao Ishida、Makoto Tokunaga

  DOI：10.1021/ol3027363

  日期：2012.12.21

  Hydrolytic enantioselective protonation of dienyl esters and a beta-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active alpha,beta-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).