8-propyl-3,3a,8,8a-tetrahydro-1H-indeno<1,2-c>furan-1-one | 143994-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 8-propyl-3,3a,8,8a-tetrahydro-1H-indeno<1,2-c>furan-1-one
• 英文别名: (3aR,4R,8bR)-4-propyl-1,3a,4,8b-tetrahydroindeno[1,2-c]furan-3-one
• CAS: 143994-23-4
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: YCBYVAPPIRGJPJ-RWMBFGLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 sodium periodate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 19.0h， 生成 8-propyl-3,3a,8,8a-tetrahydro-1H-indeno<1,2-c>furan-1-one
  参考文献：
  名称：

  A Breakthrough for the Photochemical Arylation in the 3-(Phenylmethyl)-2(5H)-furanone system Leading to the Tetrahydroindenofuranone System

  摘要：

  The photochemistry of the 'central methane'-substituted 3-benzyl-2(5H)-furanone system (1) is described. Despite its di-pi-methane structure, photochemical arylation was found to predominate in place of the di-pi-methane rearrangement, and gave substituted tetrahydroindenofuranones (2) in good yields.

  DOI：

  10.3987/com-92-6034

文献信息

• Michael Addition of Ortho-Lithiated Aryloxiranes to α,β-Unsaturated Malonates: Synthesis of Tetrahydroindenofuranones
  作者：Antonio Salomone、Vito Capriati、Saverio Florio、Renzo Luisi

  DOI：10.1021/ol800437s

  日期：2008.5.1

  A short and efficient synthesis of tetrahydroindenofuranones based on the Michael addition of ortho-lithiated aryloxiranes to alkylidene malonates followed by the nucleophilic oxirane ring-opening and subsequent lactonization is described. The methodology has been applied to the synthesis of a structural analogue of epipodophyllotoxins.

  描述了基于将邻甲硅烷基化的芳基氧杂环戊烷向亚烷基丙二酸酯的迈克尔加成，然后亲核的环氧乙烷开环和随后的内酯​​化的短而有效的合成四氢茚并呋喃酮的方法。该方法已经应用于表鬼臼毒素的结构类似物的合成。
• Furan-2(3H)- and 2(5H)-ones. Part 5. Photoreactions of 3-benzylfuran2(5H)-ones; cyclisation to indenofuranones
  作者：Osamu Muraoka、Genzoh Tanabe、Kyohko Sano、Toshie Minematsu、Takefumi Momose

  DOI：10.1039/p19940001833

  日期：——

  The effect of substitution at the 'central methane' on the photoreactivity of 3-benzylfuran-2(5H)ones 5a-g was investigated. Despite its di-pi-methane structure, photochemical arylation was effected to give substituted indenofuranones 6 in good yields. Only the substitution by phenyl caused the di-pi-methane rearrangement to give a cyclopropanofuranone 18g in moderate yield.
• A Breakthrough for the Photochemical Arylation in the 3-(Phenylmethyl)-2(5H)-furanone system Leading to the Tetrahydroindenofuranone System
  作者：Osamu Muraoka、Genzoh Tanabe、Kyoko Sano、Takefumi Momose

  DOI：10.3987/com-92-6034

  日期：——

  The photochemistry of the 'central methane'-substituted 3-benzyl-2(5H)-furanone system (1) is described. Despite its di-pi-methane structure, photochemical arylation was found to predominate in place of the di-pi-methane rearrangement, and gave substituted tetrahydroindenofuranones (2) in good yields.