(11S)-6α-hydroxy-3-oxo-guaia-4,10(14)-dien-12-oic acid-lactone | 23811-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (11S)-6α-hydroxy-3-oxo-guaia-4,10(14)-dien-12-oic acid-lactone
• 英文别名: (11S)-6α-Hydroxy-3-oxo-guaja-4,10(14)-dien-12-saeure-lacton；(3S,3aS,6aS,9bS)-3,9-dimethyl-6-methylidene-3a,4,5,6a,7,9b-hexahydro-3H-azuleno[4,5-b]furan-2,8-dione
• CAS: 23811-43-0
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: ZPFPMEDVFAQCNF-AEHQLWAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (11S)-6α-hydroxy-3-oxo-guaia-4,10(14)-dien-12-oic acid-lactone 在 吡啶 、 1-pentynyl copper 、 lithium aluminium tetrahydride 、 水 、 sodium acetate 、 铬酸 、 溶剂黄146 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 10.0h， 生成 (3aS)-3-甲基-5alpha-[(R)-1,5-二甲基-4-己烯基]-8-亚甲基-1,3aalpha,4,5,6,7,8,8abeta-八氢薁-4alpha-醇
  参考文献：
  名称：

  Highly stereoselective total syntheses of (+)-pachydictyol A and (-)-dictyolene, novel marine diterpenes from brown seaweeds of the family dictyotaceae

  摘要：

  DOI：

  10.1021/ja00536a036
• 作为产物：
  描述：

  O-acetylisophotosantonic lactone 在 吡啶 、 氢氧化钾 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 1.42h， 生成 (11S)-6α-hydroxy-3-oxo-guaia-4,10(14)-dien-12-oic acid-lactone
  参考文献：
  名称：

  Highly stereoselective total syntheses of (+)-pachydictyol A and (-)-dictyolene, novel marine diterpenes from brown seaweeds of the family dictyotaceae

  摘要：

  DOI：

  10.1021/ja00536a036

文献信息

• Synthesis (in ent-form) of a novel jalcaguaianolide from Ferula arrigonii Bocchieri
  作者：Philippe Delair、Nina Kann、Andrew E. Greene

  DOI：10.1039/p19940001651

  日期：——

  A recently isolated isodehydrocostus lactone from the genus Ferula(Umbelliferae) has been stereoselectively prepared in ent-form from α-santonin by photochemical transformation to O-acetylisophotosantonic lactone followed by functional group manipulations that conclude with a one-step γ-butyrolactone →Δα,β-butenolide conversion; the synthesis corroborates both the structure and the relative and absolute

  从该属甲最近分离isodehydrocostus内酯阿魏（伞形科植物）已得到立体选择性地制备ENT -形式从α-山道年通过光化学转化为ö -acetylisophotosantonic内酯，随后，与一步法γ丁内酯→Δ结束官能团操作α ，β-丁烯内酯转化；合成证实了天然产物的结构以及相对和绝对立体化学。
• Barton et al., Journal of the Chemical Society, 1957, p. 929,934
  作者：Barton et al.

  DOI：——

  日期：——
• Ultrasound assisted reductive cleavage of eudesmane and guaiane γ-enonelactones. Synthesis of 1α,7α,10αH-guaian-4,11-dien-3-one and hydrocolorenone from santonin
  作者：Gonzalo Blay、Victoria Bargues、Luz Cardona、Begoña Garcı́a、José R Pedro

  DOI：10.1016/s0040-4020(01)00986-3

  日期：2001.11

  Ultrasound enhances the rate of reductive cleavage of the C-6-oxygen bond of sesquiterpene enonelactones. trans-Eudesmanolides 1c-1g, cis-eudesmanolides 2a-2c, and trans-guaianolides 4a-4d react with Zn in acetic acid-H2O under sonochemical conditions to afford the corresponding sesquiterpene. acids 3a-3g and 5a-5d, respectively in good yields. Starting from 5d two natural guaianes 1 alpha ,7 alpha ,10 alphaH-guaian-4, 11-dien-3-one (6) and hydrocolorenone (7) have been prepared in good yields through a straightforward sequence. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Highly stereoselective total syntheses of (+)-pachydictyol A and (-)-dictyolene, novel marine diterpenes from brown seaweeds of the family dictyotaceae
  作者：Andrew E. Greene

  DOI：10.1021/ja00536a036

  日期：1980.7