o-hydroxy-p-quinone methide diterpenoid

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: o-hydroxy-p-quinone methide diterpenoid
• 英文别名: (4bR,8aR)-4-hydroxy-2-(2-hydroxyethyl)-1,4b,8,8-tetramethyl-5,6,7,8a-tetrahydrophenanthrene-3,9-dione
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: HAYDAXBKYUCVMG-QUCCMNQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二甲醇缩甲醛 、 o-hydroxy-p-quinone methide diterpenoid 在 四磷十氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以66%的产率得到(4bS,8aS)-4-hydroxy-2-(2-(methoxymethoxy)ethyl)-1,4b,8,8-tetramethyl-4b,5,6,7,8,8a-hexahydrophenanthrene-3,9-dione
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of an Antifungal Tricyclic o-Hydroxy-p-Quinone Methide Diterpenoid

  摘要：

  A convergent route has been developed to synthesize an antifungal tricyclic o-hydroxy-p-quinone methide diterpenoid and ana- logues. A Li/naphthalene-mediated reductive alkylation was employed for coupling beta-cyclocitral and the corresponding benzyl chloride, while a BBr3- mediated one-pot bis-demethylation and intramolecular Friedel Crafts alkylation was used to assemble the tricyclic molecular skeleton. The structure activity relationship of the diterpenoid was assessed on the basis of antiproliferation assays of the natural product and analogues against strains of pathogenic yeasts and filamentous fungi.

  DOI：

  10.1021/jo4013964
• 作为产物：
  描述：

  methyl 3-bromo-4,5-dimethoxy-2-methylbenzoate 在 sodium periodate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四氧化锇 、 氯化亚砜 、 萘 、 三叔丁基膦 、 三溴化硼 、 lithium 、 三乙酰氧基硼氢化钠 、 二异丁基氢化铝 、 溶剂黄146 、 N-甲基吗啉氧化物 、 silver(l) oxide 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 丙酮 、 甲苯 、 乙腈 、 叔丁醇 、 苯 为溶剂， 反应 19.5h， 生成 o-hydroxy-p-quinone methide diterpenoid
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of an Antifungal Tricyclic o-Hydroxy-p-Quinone Methide Diterpenoid

  摘要：

  A convergent route has been developed to synthesize an antifungal tricyclic o-hydroxy-p-quinone methide diterpenoid and ana- logues. A Li/naphthalene-mediated reductive alkylation was employed for coupling beta-cyclocitral and the corresponding benzyl chloride, while a BBr3- mediated one-pot bis-demethylation and intramolecular Friedel Crafts alkylation was used to assemble the tricyclic molecular skeleton. The structure activity relationship of the diterpenoid was assessed on the basis of antiproliferation assays of the natural product and analogues against strains of pathogenic yeasts and filamentous fungi.

  DOI：

  10.1021/jo4013964

文献信息

• US5929124A
  申请人：——

  公开号：US5929124A

  公开（公告）日：1999-07-27
• Total Synthesis and Biological Evaluation of an Antifungal Tricyclic <i>o</i>-Hydroxy-<i>p</i>-Quinone Methide Diterpenoid
  作者：Jinhua Huang、Dylan Foyle、Xiaorong Lin、Jiong Yang

  DOI：10.1021/jo4013964

  日期：2013.9.20

  A convergent route has been developed to synthesize an antifungal tricyclic o-hydroxy-p-quinone methide diterpenoid and ana- logues. A Li/naphthalene-mediated reductive alkylation was employed for coupling beta-cyclocitral and the corresponding benzyl chloride, while a BBr3- mediated one-pot bis-demethylation and intramolecular Friedel Crafts alkylation was used to assemble the tricyclic molecular skeleton. The structure activity relationship of the diterpenoid was assessed on the basis of antiproliferation assays of the natural product and analogues against strains of pathogenic yeasts and filamentous fungi.