rac-(3aR,7aR,E)-3-(4-hydroxybenzylidene)-7a-methyl-2,3,3a,4-tetrahydrobenzofuran-5(7aH)-one | 1423043-06-4

• 分子结构分类: 有机化合物
• 英文名称: rac-(3aR,7aR,E)-3-(4-hydroxybenzylidene)-7a-methyl-2,3,3a,4-tetrahydrobenzofuran-5(7aH)-one
• 英文别名: (3aS,7aS,E)-3-(4-hydroxybenzylidene)-7a-methyl-2,3,3a,4-tetrahydrobenzofuran-5(7aH)-one
• CAS: 1423043-06-4
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: PWBXLRNBXDNIST-HFWIMWPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-methyl-4-(prop-2-yn-1-yloxy)cyclohexa-2,5-dien-1-one 、 4-羟基苯硼酸 在 palladium(II) trifluoroacetate 、 对苯醌 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到rac-(3aR,7aR,E)-3-(4-hydroxybenzylidene)-7a-methyl-2,3,3a,4-tetrahydrobenzofuran-5(7aH)-one
  参考文献：
  名称：

  Palladium-Catalyzed Regioselective Domino Cyclization of Cyclohexadienones

  摘要：

  A mild and efficient Pd-catalyzed arylative domino carbocyclization of cyclohexadienone-containing 1,6-enynes is described. The reaction tolerates a variety of functionalized boronic acids to afford a cis-fused bicyclic framework containing an alpha,beta-unsaturated ketone with excellent regio- and diastereoselectivity in good yields. The tandem process proceeds with beta-arylation of propargylic ether followed by conjugate addition of a vinyl palladium intermediate and subsequent protonolysis of a palladium enolate.

  DOI：

  10.1021/acs.joc.5b00493

文献信息

• Enantioselective Rh-Catalyzed Domino Transformations of Alkynylcyclohexadienones with Organoboron Reagents
  作者：Juliane Keilitz、Stephen G. Newman、Mark Lautens

  DOI：10.1021/ol400363f

  日期：2013.3.1

  A new enantioselective rhodium-catalyzed domino reaction is described that gives access to fused heterocycles by desymmetrization of alkyne-tethered cyclohexadienones. Two new C–C bonds and two stereocenters are formed in one step with good enantioselectivity. In contrast to prior reports, it was found that a vinylidene is not involved in the product formation but that syn-addition of the rhodium-aryl

  描述了一种新的对映体选择性的铑催化的多米诺骨牌反应，该反应通过炔烃连接的环己二酮的不对称化获得稠合的杂环。一步就形成了两个新的C–C键和两个立体中心，具有良好的对映选择性。与先前的报道相反，发现亚乙烯基不参与产物形成，但是发生了铑-芳基物质向炔烃的顺式加成。