3,5-cis-marmelo oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: 3,5-cis-marmelo oxide
• 英文别名: marmelo oxide B；(+)-Marmelo oxide；Marmelo oxide A；(2R,4R)-4-methyl-2-[(1E)-3-methylbuta-1,3-dienyl]oxolane
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: SULWOTZUSYCRIP-CFUOYWMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,7-dimethyl-4,6-octadien-1-ol 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ palladium diacetate 、 三异丁基铝 、 1,2-双(二苯基膦)乙烷 、 对苯醌 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 38.0h， 生成 3,5-cis-marmelo oxide
  参考文献：
  名称：

  Synthesis of furanoid terpenes via an efficient palladium-catalyzed cyclization of 4,6-dienols

  摘要：

  The total syntheses of marmelo oxides A and B and a terpene alcohol found in peppermint oil are described. The key steps in these syntheses are the regioselective palladium-catalyzed allylic substitution of 4 and 11 to 6a and 12, respectively, and the regioselective palladium-catalyzed cyclization of 8 and 14 to 9a, 9b, and 15, respectively. The relative stereochemistry of marmelo oxides A and B was established by NOE measurements.

  DOI：

  10.1021/jo00018a027

文献信息

• Nishida, Yoshihiro; Ohrui, Hiroshi; Meguro, Hiroshi, Agricultural and Biological Chemistry, 1983, vol. 47, # 12, p. 2969 - 2972
  作者：Nishida, Yoshihiro、Ohrui, Hiroshi、Meguro, Hiroshi

  DOI：——

  日期：——
• Nishida, Yoshihiro; Fukushima, Yuko; Ohrui, Hiroshii, Agricultural and Biological Chemistry, 1984, vol. 48, # 5, p. 1217 - 1222
  作者：Nishida, Yoshihiro、Fukushima, Yuko、Ohrui, Hiroshii、Meguro, Heroshi

  DOI：——

  日期：——
• Synthesis of furanoid terpenes via an efficient palladium-catalyzed cyclization of 4,6-dienols
  作者：Pher G. Andersson、Jan E. Baeckvall

  DOI：10.1021/jo00018a027

  日期：1991.8

  The total syntheses of marmelo oxides A and B and a terpene alcohol found in peppermint oil are described. The key steps in these syntheses are the regioselective palladium-catalyzed allylic substitution of 4 and 11 to 6a and 12, respectively, and the regioselective palladium-catalyzed cyclization of 8 and 14 to 9a, 9b, and 15, respectively. The relative stereochemistry of marmelo oxides A and B was established by NOE measurements.