(1S,4aS,9aS)-7-chloro-3-methyl-9-oxo-1-(2-oxoethyl)-4,4a,9,9a-tetrahydro-1H-xanthene-9a-carbonitrile | 1402805-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (1S,4aS,9aS)-7-chloro-3-methyl-9-oxo-1-(2-oxoethyl)-4,4a,9,9a-tetrahydro-1H-xanthene-9a-carbonitrile
• 英文别名: (8S,8aS,10aS)-2-chloro-6-methyl-9-oxo-8-(2-oxoethyl)-8,10a-dihydro-5H-xanthene-8a-carbonitrile
• CAS: 1402805-81-5
• 化学式: C₁₇H₁₄ClNO₃
• 分子量: 315.756
• InChiKey: APFOENNUGPNEND-XNJJOIOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四溴化碳 、 (1S,4aS,9aS)-7-chloro-3-methyl-9-oxo-1-(2-oxoethyl)-4,4a,9,9a-tetrahydro-1H-xanthene-9a-carbonitrile 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以98%的产率得到(1S,4aS,9aS)-7-chloro-1-(3,3-dibromoallyl)-3-methyl-9-oxo-4,4a,9,9a-tetrahydro-1H-xanthene-9a-carbonitrile
  参考文献：
  名称：

  Enantioselective H-Bond-Directing Approach for Trienamine-mediated Reactions in Asymmetric Synthesis

  摘要：

  Right direction: The presented enantioselective strategy for the preparation of diversely functionalized tetrahydroxanthones is based on a trienamine-mediated cycloaddition between 2,4-dieneals and activated chromones. It is possibile to control the stereochemical outcome of such reactions by employing an H-bond-directing aminocatalyst.

  DOI：

  10.1002/anie.201204790
• 作为产物：
  描述：

  6-氯色酮-3-腈 、 5-methyl-2,4-hexadienal 在 N,N-二乙基乙酰胺 、 (S)-2-(((2-((3,5-bis(trifluoromethyl)phenyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)methyl)pyrrolidin-1-ium 2,2,2-trifluoroacetate 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以98%的产率得到(1S,4aS,9aS)-7-chloro-3-methyl-9-oxo-1-(2-oxoethyl)-4,4a,9,9a-tetrahydro-1H-xanthene-9a-carbonitrile
  参考文献：
  名称：

  Enantioselective H-Bond-Directing Approach for Trienamine-mediated Reactions in Asymmetric Synthesis

  摘要：

  Right direction: The presented enantioselective strategy for the preparation of diversely functionalized tetrahydroxanthones is based on a trienamine-mediated cycloaddition between 2,4-dieneals and activated chromones. It is possibile to control the stereochemical outcome of such reactions by employing an H-bond-directing aminocatalyst.

  DOI：

  10.1002/anie.201204790