(+/-)-furodizin | 70546-62-2

• 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: (+/-)-furodizin
• 英文别名: furodysin；(4aS,8aR)-6,9,9-trimethyl-4a,7,8,8a-tetrahydro-4H-benzo[f][1]benzofuran
• CAS: 70546-62-2；115889-38-8；129783-56-8
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: DIPYJSWOBDKTRL-CHWSQXEVSA-N

物化性质

• 沸点：
  276.1±29.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

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：

  (+/-)-furodizin 在 polystyrene-bound rose bengal 、 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(5aS,9aR)-1,1,7-Trimethyl-3-oxo-1,5,5a,8,9,9a-hexahydro-benzo[c]oxepin-(4Z)-ylidene]-acetaldehyde 、 2-hydroxy-4-[[(1S,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]methyl]-2H-furan-5-one
  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：

  (+)-内-3,9-二溴樟脑 在 sodium hydroxide 、 sodium tetrahydroborate 、 氨 、 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 8.0h， 生成 (+/-)-furodizin
  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。
• VAILLANCOURT, VALERIE;AGHARAHIMI, MOHAMAD R.;SUNDRAM, UMA N.;RICHOU, OLIV+, J. ORG. CHEM., 56,(1991) N, C. 378-387
  作者：VAILLANCOURT, VALERIE、AGHARAHIMI, MOHAMAD R.、SUNDRAM, UMA N.、RICHOU, OLIV+

  DOI：——

  日期：——