(S)-3-Hydroxy-4,7a-dimethyl-7,7a-dihydro-3H,6H-isobenzofuran-1,5-dione | 548446-27-1

• 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: (S)-3-Hydroxy-4,7a-dimethyl-7,7a-dihydro-3H,6H-isobenzofuran-1,5-dione
• 英文别名: (7aS)-3-hydroxy-4,7a-dimethyl-6,7-dihydro-3H-2-benzofuran-1,5-dione
• CAS: 548446-27-1
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: GJSBNMZJDAQQPN-HTLJXXAVSA-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：

  (S)-3-Hydroxy-4,7a-dimethyl-7,7a-dihydro-3H,6H-isobenzofuran-1,5-dione 在 sodium tetrahydroborate 、 jones reagent 、 cerium(III) chloride 作用下， 生成 (S)-(+)-4,7a-dimethyl-7,7a-dihydro-2-benzofuran-1,5(3H,6H)-dione
  参考文献：
  名称：

  Enantioselective syntheses and resolution of the key white intermediate for the synthesis of trisporic acids

  摘要：

  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

  DOI：

  10.1016/0957-4166(96)00109-7
• 作为产物：
  描述：

  (3R,7aS)-4,7a-dimethyl-3-[[(1S,2R,3R,4S)-4,7,7-trimethyl-3-naphthalen-1-yl-2-bicyclo[2.2.1]heptanyl]oxy]-6,7-dihydro-3H-2-benzofuran-1,5-dione 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (S)-3-Hydroxy-4,7a-dimethyl-7,7a-dihydro-3H,6H-isobenzofuran-1,5-dione
  参考文献：
  名称：

  Enantioselective syntheses and resolution of the key white intermediate for the synthesis of trisporic acids

  摘要：

  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

  DOI：

  10.1016/0957-4166(96)00109-7

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.
• 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.
• 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