(4S,8S)-8,11,13-trimethoxy-4-methyl-1,4,5,6,7,8,9,10-octahydro-2H-3-benzoxacyclododecine-2,10-dione | 1000866-28-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (4S,8S)-8,11,13-trimethoxy-4-methyl-1,4,5,6,7,8,9,10-octahydro-2H-3-benzoxacyclododecine-2,10-dione
• 英文别名: (5S,9S)-9,13,15-trimethoxy-5-methyl-4-oxabicyclo[10.4.0]hexadeca-1(12),13,15-triene-3,11-dione
• CAS: 1000866-28-3
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: YHEULPDWCVJBFY-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,8S)-8,11,13-trimethoxy-4-methyl-1,4,5,6,7,8,9,10-octahydro-2H-3-benzoxacyclododecine-2,10-dione 在 aluminium(III) iodide 、 四丁基碘化铵 、 盐酸 、 水 作用下， 以 苯 为溶剂， 反应 0.25h， 以65%的产率得到(4S,8S)-11,13-dihydroxy-8-methoxy-4-methyl-1,4,5,6,7,8,9,10-octahydro-2H-3-benzoxacyclododecine-2,10-dione
  参考文献：
  名称：

  Stereoseletive Total Synthesis of 11-α- and 11-β-Methoxycurvularins

  摘要：

  Total synthesis of 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin has been accomplished in a highly stereoselective manner by utilizing Jacobsen hydrolytic kinetic resolution, Maruoka asymmetric allylation and intramolecular Friedel-Crafts acylation as key steps.

  DOI：

  10.1055/s-0029-1218621
• 作为产物：
  描述：

  (3S,7S)-7-[2-(3,5-dimethoxyphenyl)acetyl]oxy-3-methoxyoctanoic acid 在 三氟乙酸 、 三氟乙酸酐 作用下， 以42%的产率得到(4S,8S)-8,11,13-trimethoxy-4-methyl-1,4,5,6,7,8,9,10-octahydro-2H-3-benzoxacyclododecine-2,10-dione
  参考文献：
  名称：

  First Total Syntheses and Spectral Data Corrections of 11-α-Methoxycurvularin and 11-β-Methoxycurvularin

  摘要：

  [Graphics]Concise and efficient total syntheses of 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin were accomplished for the first time. The three-component linchpin coupling and intramolecular acylation reactions were key steps, in which we found the spectral data of 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin, reported in the literature, were reversed with each other.

  DOI：

  10.1021/jo701885n

文献信息

• First Total Syntheses and Spectral Data Corrections of 11-α-Methoxycurvularin and 11-β-Methoxycurvularin
  作者：Qiren Liang、Yongquan Sun、Binxun Yu、Xuegong She、Xinfu Pan

  DOI：10.1021/jo701885n

  日期：2007.12.1

  [Graphics]Concise and efficient total syntheses of 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin were accomplished for the first time. The three-component linchpin coupling and intramolecular acylation reactions were key steps, in which we found the spectral data of 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin, reported in the literature, were reversed with each other.
• Stereoselective syntheses of 11-α-methoxycurvularin and 11-β-methoxycurvularin
  作者：G. Venkateswar Reddy、R. Sateesh Chandra Kumar、K. Suresh Babu、J. Madhusudana Rao

  DOI：10.1016/j.tetlet.2009.04.120

  日期：2009.7

  A stereoselective synthesis of potent cytotoxic macrolides, 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin has been accomplished. The synthesis entailed Maruoka asymmetric allylation to introduce the stereocentres at C-11 and the key fragment was installed by using Grubbs cross-metathesis followed by CBS-reduction. (C) 2009 Published by Elsevier Ltd.
• Stereoseletive Total Synthesis of 11-α- and 11-β-Methoxycurvularins
  作者：J. Yadav、A. Raju、K. Ravindar、B. Reddy

  DOI：10.1055/s-0029-1218621

  日期：2010.3

  Total synthesis of 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin has been accomplished in a highly stereoselective manner by utilizing Jacobsen hydrolytic kinetic resolution, Maruoka asymmetric allylation and intramolecular Friedel-Crafts acylation as key steps.