puupehenol | 189098-18-8

• 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: puupehenol
• 英文别名: (4aS,6aS,12aR,12bS)-4,4,6a,12b-tetramethyl-1,2,3,4a,5,6,12,12a-octahydrobenzo[a]xanthene-9,10-diol
• CAS: 189098-18-8
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: POYORKRQQXVDST-YHELAOLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  puupehenol 在 silver(l) oxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以94%的产率得到puupehenone
  参考文献：
  名称：

  First Enantiospecific Synthesis of the Antitumor Marine Sponge Metabolite (−)-15-Oxopuupehenol from (−)-Sclareol

  摘要：

  [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.

  DOI：

  10.1021/ol047332j
• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 在 咪唑 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 叔丁基锂 、 silica gel 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 四氯化碳 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.08h， 生成 puupehenol
  参考文献：
  名称：

  Enantiospecific synthesis of (+)-puupehenone from (−)-sclareol and protocatechualdehyde

  摘要：

  The first enantiospecific synthesis of the antitumor and cholesteryl ester transfer protein (CETP) inhibitor (+)-puupehenone (19) from (-)-sclareol (10) and protocatechualdehyde (4) is described. The key steps of the reaction sequence are the organoselenium-induced cyclization of the mixture of regioisomers 15a-b to give 16 and 17, with complete diastereoselectivity, and the simultaneous removal of benzyl and phenylselenyl groups of 16 and 17 by treating with Raney Ni. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00305-5

文献信息

• Protecting-group-free synthesis of haterumadienone- and puupehenone-type marine natural products
  作者：Hong-Shuang Wang、Hui-Jing Li、Jun-Li Wang、Yan-Chao Wu

  DOI：10.1039/c7gc00704c

  日期：——

  A divergent and expeditious access to haterumadienone- and puupehenone-type marine natural products has been achieved by using a newly developed hemiacetalization/dehydroxylation/hydroxylation/retro-hemiacetalization tandem reaction as one of the key steps. Its applicability is showcased by the first synthesis of haterumadienone, 20-hydroxyhaterumadienone, 20-epihydroxy-haterumadienone and 20-acetoxy-haterumadienone

  通过使用新开发的半缩醛化/脱羟基/羟基化/逆半缩醛化串联反应作为关键步骤之一，已获得了迅速而多样的途径获得哈雷马二烯酮和布芬二酮类海洋天然产品的途径。它的适用性通过首次合成的方法包括合成的帽子花呢二烯酮，20-羟基帽子酸二烯酮，20-表羟基帽子酸二烯酮和20-乙酰氧基帽子酸二烯酮，以及容易合成的葛根酮，葛根二酮和葛根酚。合成是有效的，并且原子和步骤经济的（从市售起始原料开始6至9个步骤），并且不需要保护基团和过渡金属。
• A Convenient Enantiospecific Route towards Bioactive Merosesquiterpenes by Cationic-Resin-Promoted Friedel-Crafts Alkylation with α,β-Enones
  作者：Enrique Alvarez-Manzaneda、Rachid Chahboun、Eduardo Cabrera、Esteban Alvarez、Ali Haidour、Jose Miguel Ramos、Ramón Alvarez-Manzaneda、Rubén Tapia、Hakima Es-Samti、Antonio Fernández、Inmaculada Barranco

  DOI：10.1002/ejoc.200801174

  日期：2009.3

  An enantiospecific route towards bioactive merosesquiterpenes, based on the cationic-resin-promoted Friedel–Crafts alkylation of alkoxyarenes with an α,β-unsaturated ketone, is reported. Reaction of ketone 11 with 3,4-methylenedioxyphenol afforded the corresponding chromene. Treatment of 11 with protected phenol 20 gave aryl nordrimane ketone 21, a suitable intermediate in the synthesis of bioactive

  据报道，基于阳离子树脂促进的 Friedel-Crafts 烷基化烷氧基芳烃与 α,β-不饱和酮的生物活性merosesquiterpenes 的对映特异性途径。酮 11 与 3,4-亚甲二氧基苯酚反应得到相应的色烯。用受保护的苯酚 20 处理 11 得到芳基去甲烷酮 21，这是合成生物活性merosesquiterpenes 及其 8-epi 衍生物的合适中间体。通过利用这种方法，描述了 (+)-puupehenone 和其他相关代谢物的正式合成，通过三氟甲磺酸酯 25。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• CN116947615
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• Enantiospecific synthesis of (+)-puupehenone from (−)-sclareol and protocatechualdehyde
  作者：Alejandro F. Barrero、Enrique J. Alvarez-Manzaneda、Rachid Chahboun

  DOI：10.1016/s0040-4039(97)00305-5

  日期：1997.3

  The first enantiospecific synthesis of the antitumor and cholesteryl ester transfer protein (CETP) inhibitor (+)-puupehenone (19) from (-)-sclareol (10) and protocatechualdehyde (4) is described. The key steps of the reaction sequence are the organoselenium-induced cyclization of the mixture of regioisomers 15a-b to give 16 and 17, with complete diastereoselectivity, and the simultaneous removal of benzyl and phenylselenyl groups of 16 and 17 by treating with Raney Ni. (C) 1997 Elsevier Science Ltd.