(2R,4'S)-7'-methoxy-4'-(nitromethyl)spiro[3,4-dihydronaphthalene-2,3'-4H-chromene]-1,2'-dione | 1338566-42-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: (2R,4'S)-7'-methoxy-4'-(nitromethyl)spiro[3,4-dihydronaphthalene-2,3'-4H-chromene]-1,2'-dione
• CAS: 1338566-42-9
• 化学式: C₂₀H₁₇NO₆
• 分子量: 367.358
• InChiKey: YKWDDHMHYGIIIR-OXJNMPFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2R,4'S)-7'-methoxy-4'-(nitromethyl)spiro[3,4-dihydronaphthalene-2,3'-4H-chromene]-1,2'-dione
  参考文献：
  名称：

  Asymmetric Synthesis of 3,4-Dihydrocoumarin Motif with an All-Carbon Quaternary Stereocenter via a Michael–Acetalization Sequence with Bifunctional Amine-thiourea Organocatalysts

  摘要：

  Asymmetric domino Michael acetalization reactions of 2-hydroxynitrostyrene and 2-oxocyclohexanecarbaldehyde with a bifunctional thioureatertiary-amine organocatalyst, e.g., the Takemoto catalyst, followed by oxidation providing the 1',3-spiro-2'-oxocyclohexan-3,4-dihydrocoumarin having one all-carbon quaternary stereocenter with excellent diastereo- and enantioselectivities (up to >99% ee), are described. The structures and absolute configurations of the products were confirmed by X-ray analysis.

  DOI：

  10.1021/ol202331j

文献信息

• Asymmetric Synthesis of 3,4-Dihydrocoumarin Motif with an All-Carbon Quaternary Stereocenter <i>via</i> a Michael–Acetalization Sequence with Bifunctional Amine-thiourea Organocatalysts
  作者：Bor-Cherng Hong、Prakash Kotame、Gene-Hsiang Lee

  DOI：10.1021/ol202331j

  日期：2011.11.4

  Asymmetric domino Michael acetalization reactions of 2-hydroxynitrostyrene and 2-oxocyclohexanecarbaldehyde with a bifunctional thioureatertiary-amine organocatalyst, e.g., the Takemoto catalyst, followed by oxidation providing the 1',3-spiro-2'-oxocyclohexan-3,4-dihydrocoumarin having one all-carbon quaternary stereocenter with excellent diastereo- and enantioselectivities (up to >99% ee), are described. The structures and absolute configurations of the products were confirmed by X-ray analysis.