3-[[(1S,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]methyl]furan

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-[[(1S,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]methyl]furan
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: BZCPZUVDLXYBLX-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  3-[[(1S,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]methyl]furan 在 sodium hydroxide 、 sodium tetrahydroborate 、 mercury(II) nitrate 作用下， 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
• 作为产物：
  描述：

  反式-薄荷基-2,8-二烯-1-醇 在 4-二甲氨基吡啶 作用下， 生成 3-[[(1S,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]methyl]furan
  参考文献：
  名称：

  A new synthesis of (−)-furodysin

  摘要：

  A synthesis of furodysin from tranrs-limonoene oxide involves trasformation into the phenylcarbamate of 2,8-menthadien-1-ol, allylic displacenlelle with lithium di-(beta-furylmethyl)cuprate, and cyclization.

  DOI：

  10.1016/0040-4039(94)02464-m

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。
• 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：——