19,20-di-O-methylenepuupehenol | 197655-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 19,20-di-O-methylenepuupehenol
• 英文别名: (1S,13R,14S,19S)-1,14,18,18-tetramethyl-2,6,8-trioxapentacyclo[11.8.0.03,11.05,9.014,19]henicosa-3,5(9),10-triene
• CAS: 197655-87-1
• 化学式: C₂₂H₃₀O₃
• 分子量: 342.478
• InChiKey: SACUDAWUVXNSEM-MXNKGDRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  19,20-di-O-methylenepuupehenol 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以45%的产率得到(1S,13R,14S,19S)-1,14,18,18-tetramethyl-2,6,8-trioxapentacyclo[11.8.0.03,11.05,9.014,19]henicosa-3,5(9),10-trien-12-one
  参考文献：
  名称：

  Total synthesis of both enantiomers of 15-oxopuupehenol methylendioxy derivatives

  摘要：

  The total synthesis of both enantiomers of puupehenol and 15-oxopuupehenol as methylenedioxy derivatives is described. The key steps of the synthesis are the regioselective transformation of 10 to 11 and the stereoselective cyclization of 12 to 13. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01683-3
• 作为产物：
  描述：

  (-)-补身醇 在 sodium tetrahydroborate 、 camphor-10-sulfonic acid 、 叔丁基锂 、 pyridinium chlorochromate 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.75h， 生成 19,20-di-O-methylenepuupehenol
  参考文献：
  名称：

  Total synthesis of both enantiomers of 15-oxopuupehenol methylendioxy derivatives

  摘要：

  The total synthesis of both enantiomers of puupehenol and 15-oxopuupehenol as methylenedioxy derivatives is described. The key steps of the synthesis are the regioselective transformation of 10 to 11 and the stereoselective cyclization of 12 to 13. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01683-3

文献信息

• Synthesis and antitumor activity of puupehedione and related compounds
  作者：Alejandro F. Barrero、Enrique J. Alvarez-Manzaneda、Rachid Chahboun、M. Cortés、V. Armstrong

  DOI：10.1016/s0040-4020(99)00992-8

  日期：1999.12

  The first enantiospecific synthesis of bioactive marine puupehedione (2) and related compounds from (−)-sclareol (11) is reported. The antitumor activity of these compounds was assayed and compared with that of the natural products.

  据报道，首次从（-）-香紫苏醇（11）合成了生物活性海洋puupehedione（2）和相关化合物的对映体。测定这些化合物的抗肿瘤活性并将其与天然产物的抗肿瘤活性进行比较。
• NIS–PPh₃: A Selective Reagent for the Spiroannulation of <i>o</i>-Allyl Phenols. Total Synthesis of Corallidictyal D
  作者：M. José Cano、Hanane Bouanou、Rubén Tapia、Esteban Alvarez、Ramón Alvarez-Manzaneda、Rachid Chahboun、Enrique Alvarez-Manzaneda

  DOI：10.1021/jo4014047

  日期：2013.9.20

  Treatment of o-allyl phenols with catalytic NIS–PPh3 affords the corresponding spirodihydrobenzofuran derivatives in high yield with high regio- and total stereoselectivity under mild conditions. These results were utilized to achieve the first total synthesis of the protein kinase C inhibitor corallidictyal D starting from α-ionone.

  用催化性NIS-PPh 3处理邻烯丙基苯酚可在温和条件下以高收率和高区域选择性和总立体选择性提供相应的螺二氢苯并呋喃衍生物。这些结果被用来实现从α-紫罗兰酮开始的蛋白激酶C抑制剂珊瑚D的第一个全合成。
• First Enantiospecific Synthesis of the Antitumor Marine Sponge Metabolite (−)-15-Oxopuupehenol from (−)-Sclareol
  作者：E. J. Alvarez-Manzaneda、R. Chahboun、I. Barranco Pérez、E. Cabrera、E. Alvarez、R. Alvarez-Manzaneda

  DOI：10.1021/ol047332j

  日期：2005.4.14

  [GRAPHICS]A new route toward puupehenone-related bioactive metabolites from (-)-sclareol, based on the palladium(II)-mediated diastereoselective cyclization of a drimenylphenol, is described. Utilizing this, the first enantiospecific synthesis of the antitumor and antimalarial (-)-15-oxopuupehenol, together with improved syntheses of (+)-puupehenone, (+)-puupehedione, and (+)-15-cyanopuupehenone, were accomplished.
• Total synthesis of both enantiomers of 15-oxopuupehenol methylendioxy derivatives
  作者：Odón Arjona、María Garranzo、Jesús Mahugo、Eduardo Maroto、Joaquín Plumet、Beatriz Sáez

  DOI：10.1016/s0040-4039(97)01683-3

  日期：1997.10

  The total synthesis of both enantiomers of puupehenol and 15-oxopuupehenol as methylenedioxy derivatives is described. The key steps of the synthesis are the regioselective transformation of 10 to 11 and the stereoselective cyclization of 12 to 13. (C) 1997 Elsevier Science Ltd.