(3R,3aR,4R,7aS)-4-Isopropenyl-3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one | 158690-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (3R,3aR,4R,7aS)-4-Isopropenyl-3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one
• 英文别名: (3R,3aR,4R,7aS)-3,6-dimethyl-4-prop-1-en-2-yl-3a,4,5,7a-tetrahydro-3H-1-benzofuran-2-one
• CAS: 158690-89-2
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: RPZVLQNGPDCHRO-KXNHARMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,3aR,4R,7aS)-4-Isopropenyl-3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one 在 lithium aluminium tetrahydride 、 正丁基锂 、 四丙基高钌酸铵 、 4 A molecular sieve 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 、 二氯甲烷 为溶剂， 反应 10.75h， 生成 (2R)-7-[tert-butyl(dimethyl)silyl]oxy-2-[(1R,2S,6R)-2-(methoxymethoxy)-4-methyl-6-prop-1-en-2-ylcyclohex-3-en-1-yl]hept-4-yn-3-ol
  参考文献：
  名称：

  Total Synthesis of Zoanthamine Alkaloids, Part 2. Construction of the C1-C5, C6-C10, and C11-C24 Fragments of Zoanthamine.

  摘要：

  This paper describes the construction of three key intermediates 11, 15 and 23 for a projected total synthesis of the marine alkaloid zoanthamine. These building blocks, corresponding to the C-1-C-5, C-6-C-10, and C-11-C-24 fragments of the target molecule, are synthesised efficiently from (R)-gamma-hydroxymethyl-gamma-butyrolactone, methyl propiolate, and (S)-perillyl alcohol, respectively.

  DOI：

  10.3891/acta.chem.scand.51-1217
• 作为产物：
  描述：

  (1R,4R,6S)-6-methyl-4-prop-1-en-2-ylcyclohex-2-en-1-ol 在 lithium hydroxide 、 2,4-二硝基酚 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 32.5h， 生成 (3R,3aR,4R,7aS)-4-Isopropenyl-3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one
  参考文献：
  名称：

  A synthetic approach to the Zoanthamine alkaloids

  摘要：

  A synthetic approach to the marine alkaloid Zoanthamine is outlined. Starting with (-)-perillyl alcohol, the C-11 to C-20 fragment 9b has been synthesized in 12 operations and >30% overall yield. Model studies for a proposed intramolecular Diels-Alder strategy are also described

  DOI：

  10.1016/s0040-4020(01)85379-5

文献信息

• A synthetic approach to the Zoanthamine alkaloids
  作者：David Tanner、Pher G. Andersson、Lars Tedenborg、Peter Somfai

  DOI：10.1016/s0040-4020(01)85379-5

  日期：1994.1

  A synthetic approach to the marine alkaloid Zoanthamine is outlined. Starting with (-)-perillyl alcohol, the C-11 to C-20 fragment 9b has been synthesized in 12 operations and >30% overall yield. Model studies for a proposed intramolecular Diels-Alder strategy are also described
• Total Synthesis of Zoanthamine Alkaloids, Part 2. Construction of the C1-C5, C6-C10, and C11-C24 Fragments of Zoanthamine.
  作者：David Tanner、Lars Tedenborg、Peter Somfai、Lars Skattebøl、Connie N. Rosendahl

  DOI：10.3891/acta.chem.scand.51-1217

  日期：——

  This paper describes the construction of three key intermediates 11, 15 and 23 for a projected total synthesis of the marine alkaloid zoanthamine. These building blocks, corresponding to the C-1-C-5, C-6-C-10, and C-11-C-24 fragments of the target molecule, are synthesised efficiently from (R)-gamma-hydroxymethyl-gamma-butyrolactone, methyl propiolate, and (S)-perillyl alcohol, respectively.