(2R,3aR,4'S,5'S,6aS,E)-4'-hydroxy-5'-((R)-3-hydroxybutyl)-4-((R)-5-methyldihydrofuran-2(3H)-ylidene)hexahydro-3'H-spiro[cyclopenta[b]furan-2,2'-furan]-5(3H)-one | 1625643-91-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3aR,4'S,5'S,6aS,E)-4'-hydroxy-5'-((R)-3-hydroxybutyl)-4-((R)-5-methyldihydrofuran-2(3H)-ylidene)hexahydro-3'H-spiro[cyclopenta[b]furan-2,2'-furan]-5(3H)-one
• 英文别名: opaliferin；(2R,3aR,4E,4'S,5'S,6aS)-4'-hydroxy-5'-[(3R)-3-hydroxybutyl]-4-[(5R)-5-methyloxolan-2-ylidene]spiro[3,3a,6,6a-tetrahydrocyclopenta[b]furan-2,2'-oxolane]-5-one
• CAS: 1625643-91-5
• 化学式: C₁₉H₂₈O₆
• 分子量: 352.428
• InChiKey: JACPLNLRQCNGQJ-FACFEIAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3aR,4'S,5'S,6aS,E)-4'-hydroxy-5'-((R)-3-hydroxybutyl)-4-((R)-5-methyldihydrofuran-2(3H)-ylidene)hexahydro-3'H-spiro[cyclopenta[b]furan-2,2'-furan]-5(3H)-one 、 4-溴苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以52%的产率得到(R)-4-((2R,3aR,4'S,5'S,6aS,E)-4'-((4-bromobenzoyl)oxy)-4-((R)-5-methyldihydrofuran-2(3H)-ylidene)-5-oxooctahydro-3'H-spiro[cyclopenta[b]furan-2,2'-furan]-5'-yl)butan-2-yl 4-bromobenzoate
  参考文献：
  名称：

  Opaliferin, a New Polyketide from Cultures of Entomopathogenic Fungus Cordyceps sp. NBRC 106954

  摘要：

  Opaliferin, a polyketide with a unique partial structure in which a cyclopentanone and tetrahydrofuran were connected with an external double bond, was isolated from the insect pathogenic fungus Cordyceps sp. NBRC 106954. The structure and relative configuration of opaliferin were determined by spectroscopic analysis and X-ray crystallography. The absolute configuration was established by anomalous dispersion effects in X-ray diffraction measurements on the crystal of di(p-bromobenzoyl) ester of opaliferin. A plausible biosynthetic pathway for opaliferin is proposed.

  DOI：

  10.1021/ol502216j