furodysinin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: furodysinin
• 英文别名: (+/-)-furodizinin；(4aR,8aS)-4,4,7-trimethyl-5,6,8a,9-tetrahydro-4aH-benzo[f][1]benzofuran
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: OSSOIKJYWQAIQR-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 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：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  furodysinin 在 氧气 、 rose bengal 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以77%的产率得到the furodysinin hydroperoxide
  参考文献：
  名称：

  Metabolites of the nudibranch Chromodoris funerea and the singlet oxygen oxidation products of furodysin and furodysinin

  摘要：

  DOI：

  10.1021/jo00368a025
• 作为产物：
  描述：

  白樟油 在 氯磺酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium naphthaleimide 、 氨 、 氢溴酸 、 溴 、 lithium 、 mercury(II) nitrate 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 21.0h， 生成 furodysinin
  参考文献：
  名称：

  Synthesis and absolute configuration of the antiparasitic furanosesquiterpenes (-)-furodysin and (-)-furodysinin. Camphor as a six-membered ring chiral pool template

  摘要：

  The syntheses of (-)-furodysin ((-)-2a) and (-)-furodysinin ((-)-3a) in four steps starting from (+)-9-bromocamphor (18) has been accomplished, thus establishing the absolute configuration of these and related metabolites. This was made possible by the unexpected exo selectivity in the aldol condensation of camphor-like enolates with aldehydes. This has been found to be a general phenomenon in the camphor system. Further, anionic fragmentation of the C1-C7 bond of camphor derivatives has allowed access to synthetic intermediates containing functionalized six-membered rings, thus opening up avenues from camphor to a new class of chiral pool elements not currently available from chiral pool substances.

  DOI：

  10.1021/jo00001a069

文献信息

• Chemistry of natural compounds and bioorganic chemistry Synthesis of (�)-furodizinin and (�)-furodizin
  作者：A. M. Moiseenkov、A. V. Lozanoya、A. A. Surkova、A. V. Buevich、V. V. Veselovsky

  DOI：10.1007/bf01431820

  日期：1996.7

  The racemic forms of natural Omnoterpenoids, (±)-furodizinin and (±)-furodizin, were synthesized by cationic cyclization of the α or β-furylmethyl derivatives of linalool, geraniol and nerol.

  通过芳樟醇、香叶​​醇和橙花醇的 α 或 β-呋喃基甲基衍生物的阳离子环化，合成了外消旋形式的天然 Omnoterpenoids，(±)-furodizinin 和 (±)-furodizin。
• Total Synthesis of (±)-Furodysin and (±)-Furodysinin
  作者：Hiroshi Hirota、Masafumi Kitano、Ken-ichi Komatsubara、Takeyoshi Takahashi

  DOI：10.1246/cl.1987.2079

  日期：1987.10.5

  Furodysin and furodysinin, marine origin furanosesquiterpenes having a unique carbocyclic ring system, have been first synthesized as racemic forms from a cis-decalone derivative.

  呋喃地素和呋喃地素是源自海洋的呋喃并四氢萜类化合物，具有独特的碳环系统，首次以消旋形式从顺式癸酮衍生物中合成。
• Regioselective oxidation of 3-alkylfurans to 3-alkyl-4-hydroxybutenolides
  作者：Michael R. Kernan、D. John Faulkner

  DOI：10.1021/jo00247a021

  日期：1988.6
• Synthesis and absolute configuration of (-)-furodysinin. New transformations of camphor derivatives
  作者：Olivier Richou、Valerie Vaillancourt、D. John Faulkner、Kim F. Albizati

  DOI：10.1021/jo00281a002

  日期：1989.9
• Synthesis of (–)-furodysinin from (+)-limonene
  作者：Tse-Lok Ho、Rong-Jie Chein

  DOI：10.1039/cc9960001147

  日期：——

  Furodysinin is synthesised by elaboration of (1R, 2R)-(+)-limonene oxide; key reactions include a tandem Claisen rearrangement-ene reaction and trapping of a conjugate adduct of an enone providing a bicyclic precursor of the sesquiterpene.