4-(4-methoxyphenyl)-4,6,7,8-tetrahydrochromen-5-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxyphenyl)-4,6,7,8-tetrahydrochromen-5-one
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: OYXPSWMSXLDNGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1'-羟基-2',3'-去氢草蒿脑 、 1,3-环己二酮 在 ammonium tetrafluoroborate 、 [(η5-C5Me5)RuCl(μ2-SMe)2Ru(η5-C5Me5)Cl] 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以94%的产率得到4-(4-methoxyphenyl)-4,6,7,8-tetrahydrochromen-5-one
  参考文献：
  名称：

  Ruthenium-Catalyzed Cycloaddition between Propargylic Alcohols and Cyclic 1,3-Dicarbonyl Compounds via an Allenylidene Intermediate

  摘要：

  Thiolate-bridged diruthenium complexes such as [Cp*RuCl(mu(2)-SR)(2)RuCp*Cl] (Cp* = eta(5)-C5Me5; R = Me, Pr-n, Pr-i) and [CP*RuCl(mu(2)-(SPr)-Pr-i)(2)RuCp*(OH2)]OTf (OTf = OSO2CF3) promote the cycloaddition between propargylic alcohols and cyclic 1,3-dicarbonyl compounds to give either the corresponding 4,6,7,8-tetrahydrochromen-5-ones or 4H-cyclopenta[b]pyran-5-ones in high yields with complete regioselectivity. This catalytic cycloaddition provides a simple and one-pot synthetic protocol for a variety of substituted chromenones and cyclopenta[b]pyranones.

  DOI：

  10.1021/jo0357465

文献信息

• Ruthenium-Catalyzed Cycloaddition between Propargylic Alcohols and Cyclic 1,3-Dicarbonyl Compounds via an Allenylidene Intermediate
  作者：Yoshiaki Nishibayashi、Masato Yoshikawa、Youichi Inada、Masanobu Hidai、Sakae Uemura

  DOI：10.1021/jo0357465

  日期：2004.5.1

  Thiolate-bridged diruthenium complexes such as [Cp*RuCl(mu(2)-SR)(2)RuCp*Cl] (Cp* = eta(5)-C5Me5; R = Me, Pr-n, Pr-i) and [CP*RuCl(mu(2)-(SPr)-Pr-i)(2)RuCp*(OH2)]OTf (OTf = OSO2CF3) promote the cycloaddition between propargylic alcohols and cyclic 1,3-dicarbonyl compounds to give either the corresponding 4,6,7,8-tetrahydrochromen-5-ones or 4H-cyclopenta[b]pyran-5-ones in high yields with complete regioselectivity. This catalytic cycloaddition provides a simple and one-pot synthetic protocol for a variety of substituted chromenones and cyclopenta[b]pyranones.