4,8-dimethyl-1,5-dioxo-3-hydroxy-2-oxabicyclo<4.3.0>non-4(9)-ene | 69841-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: 4,8-dimethyl-1,5-dioxo-3-hydroxy-2-oxabicyclo<4.3.0>non-4(9)-ene
• 英文别名: 1,5(3H,6H)-Isobenzofurandione, 7,7a-dihydro-3-hydroxy-4,7a-dimethyl-；3-hydroxy-4,7a-dimethyl-6,7-dihydro-3H-2-benzofuran-1,5-dione
• CAS: 69841-90-3
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: GJSBNMZJDAQQPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,8-dimethyl-1,5-dioxo-3-hydroxy-2-oxabicyclo<4.3.0>non-4(9)-ene 在 盐酸 、 六甲基磷酰三胺 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.67h， 生成 7-E,9-E methyl trisporate B
  参考文献：
  名称：

  Stereoselective synthesis of trisporic acids A and B, their methyl esters, and trisporols A and B, hormones and prohormones of mucoraceous fungi

  摘要：

  DOI：

  10.1021/jo00225a049
• 作为产物：
  描述：

  3-甲基-2,3,4,5-四氢-2,4-呋喃二酮 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 水 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 苯 为溶剂， 反应 45.08h， 生成 4,8-dimethyl-1,5-dioxo-3-hydroxy-2-oxabicyclo<4.3.0>non-4(9)-ene
  参考文献：
  名称：

  Stereoselective synthesis of trisporic acids A and B, their methyl esters, and trisporols A and B, hormones and prohormones of mucoraceous fungi

  摘要：

  DOI：

  10.1021/jo00225a049

文献信息

• Detours en route to a total synthesis of (+)-cassiol
  作者：Marı́a I. Colombo、Juan Zinczuk、Marı́a L. Bohn、Edmundo A. Rúveda

  DOI：10.1016/s0957-4166(03)00082-x

  日期：2003.3

  A synthesis of the antiulcerogenic compound (+)-cassiol 1b has been achieved in 43% yield starting with lactol (S)-2 and sulfone 26. This short and efficient synthesis features the one-pot Julia olefination reaction of the sodium anion of (S)-2 with 26, through the key intermediate (-)-9. This synthesis has been developed as a result of exploratory experiments including different olefination reactions on 2. An attempt to synthesize the intermediate 9 by an intramolecular aldol condensation approach of the open chain precursor 4 is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Enantioselective syntheses and resolution of the key white intermediate for the synthesis of trisporic acids
  作者：JoséA. Bacigaluppo、María I. Colombo、Marcelo D. Preite、Juan Zinczuk、Edmundo A. Rúveda、Joachim Sieler

  DOI：10.1016/0957-4166(96)00109-7

  日期：1996.4

  Two asymmetric syntheses of the alkylated cyclohexenone carboxylic acid moiety, the key White intermediate (4a), of trisporic acids A, B and C are described. The syntheses feature a Michael addition in tandem with an aldol condensation as the central step. The resolution of this readily available intermediate is also described. Copyright (C) 1996 Elsevier Science
• A concise synthesis of (+)-cassiol
  作者：Marı́a I Colombo、Juan Zinczuk、Mirta P Mischne、Edmundo A Rúveda

  DOI：10.1016/s0957-4166(01)00222-1

  日期：2001.6

  A synthesis of the anti-ulcerogenic compound (+)-cassiol 1b with 43% overall yield has been achieved. This short and efficient synthesis features the one-pot Julia olefination reaction of lactol (S)-2 with sulfone 3b through the key intermediate (-)-4b. (C) 2001 Elsevier Ltd. All rights reserved.
• Synthesis of methyl 4-dihydrotrisporate B, a prohormone of
  作者：Kunihiko Takabe、James D. White

  DOI：10.1016/s0040-4039(00)94515-5

  日期：1983.1
• Stereoselective synthesis of trisporic acids A and B, their methyl esters, and trisporols A and B, hormones and prohormones of mucoraceous fungi
  作者：James D. White、Kunihiko Takabe、Michael P. Prisbylla

  DOI：10.1021/jo00225a049

  日期：1985.12