(5Z)-5-[3-(2,3-dimethoxy-4-methylphenyl)butylidene]-4-methylfuran-2-one | 682746-89-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5Z)-5-[3-(2,3-dimethoxy-4-methylphenyl)butylidene]-4-methylfuran-2-one
• CAS: 682746-89-0
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: NZOYPUBABDAXCG-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5Z)-5-[3-(2,3-dimethoxy-4-methylphenyl)butylidene]-4-methylfuran-2-one 在 三氟甲磺酸 作用下， 反应 0.25h， 以91%的产率得到7,8-dimethoxy-1,4',6-trimethylspiro[2,3-dihydro-1H-naphthalene-4,5'-furan]-2'-one
  参考文献：
  名称：

  A new approach to the pseudopterosins using an arene alkylation with a γ-methylene-γ-butyrolactone

  摘要：

  A short and practical route to the tricyclic core of an unnatural pseudopterosin diastereoisomer is presented. Key features are an arene alkylation with a gamma -methylene-gamma -butyrolactone, viz. 10 --> 14, and an elaborate reduction sequence 14 --> 17 which both proceed diastereoselectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02207-3
• 作为产物：
  描述：

  4-bromo-3-methylbut-2-en-4-olide 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 20.0h， 生成 (5Z)-5-[3-(2,3-dimethoxy-4-methylphenyl)butylidene]-4-methylfuran-2-one
  参考文献：
  名称：

  A new approach to the pseudopterosins using an arene alkylation with a γ-methylene-γ-butyrolactone

  摘要：

  A short and practical route to the tricyclic core of an unnatural pseudopterosin diastereoisomer is presented. Key features are an arene alkylation with a gamma -methylene-gamma -butyrolactone, viz. 10 --> 14, and an elaborate reduction sequence 14 --> 17 which both proceed diastereoselectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02207-3

文献信息

• Total synthesis of (±)-pseudopterosin A–F and K–L aglycone
  作者：David C. Harrowven、Melloney J. Tyte

  DOI：10.1016/j.tetlet.2004.01.060

  日期：2004.3

  A total synthesis of (±)-pseudopterosin A–F and K–L aglycone is described in which three aromatic alkylation reactions are used to construct the hexahydrophenalene ring system.

  描述了（±）-伪藻蛋白A-F和K-L糖苷配基的全合成，其中三个芳族烷基化反应用于构建六氢苯并环系统。
• A new approach to the pseudopterosins using an arene alkylation with a γ-methylene-γ-butyrolactone
  作者：David C Harrowven、Jonathan D Wilden、Melloney J Tyte、Michael B Hursthouse、Simon J Coles

  DOI：10.1016/s0040-4039(00)02207-3

  日期：2001.2

  A short and practical route to the tricyclic core of an unnatural pseudopterosin diastereoisomer is presented. Key features are an arene alkylation with a gamma -methylene-gamma -butyrolactone, viz. 10 --> 14, and an elaborate reduction sequence 14 --> 17 which both proceed diastereoselectively. (C) 2001 Elsevier Science Ltd. All rights reserved.