(4'aR,8'aR)-5',8'a-dimethyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro([1,3]dioxolane-2,2'-naphthalene) | 294202-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4'aR,8'aR)-5',8'a-dimethyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro([1,3]dioxolane-2,2'-naphthalene)
• 英文别名: (4aR,8aS)-4a,8-dimethylspiro[1,2,4,5,6,8a-hexahydronaphthalene-3,2'-1,3-dioxolane]
• CAS: 294202-65-6
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: BKZGYWGRERXFBN-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4'aR,8'aR)-5',8'a-dimethyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro([1,3]dioxolane-2,2'-naphthalene) 在 3,5-二甲基吡唑 、 chromium(VI) oxide 、 甲基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 (4aR,8aS)-5,8a-dimethyl-3,4,4a,8a-tetrahydro-1H-naphthalen-2-one
  参考文献：
  名称：

  Efficient, Highly Enantioselective Synthesis of Selina-1,3,7(11)-trien-8-one, a Major Component of the Essential Oil of Eugenia uniflora

  摘要：

  The first synthesis of selina-1,3,7(11)-trien-8-one (1), a major constituent of the essential oil from the leaves of Eugenia uniflora, has been accomplished, with excellent stereo- and regiocontrol, in eight steps and in 12% overall yield from the known octalone derivative 2a.

  DOI：

  10.1021/np000065f
• 作为产物：
  描述：

  (R)-5',8'a-Dimethyl-1',3',4',7',8',8'a-hexahydrospiro[[1,3]-dioxolane-2,2'-naphthalen]-6'-one 在 儿萘酚硼烷 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 7.75h， 生成 (4'aR,8'aR)-5',8'a-dimethyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro([1,3]dioxolane-2,2'-naphthalene)
  参考文献：
  名称：

  Efficient, Highly Enantioselective Synthesis of Selina-1,3,7(11)-trien-8-one, a Major Component of the Essential Oil of Eugenia uniflora

  摘要：

  The first synthesis of selina-1,3,7(11)-trien-8-one (1), a major constituent of the essential oil from the leaves of Eugenia uniflora, has been accomplished, with excellent stereo- and regiocontrol, in eight steps and in 12% overall yield from the known octalone derivative 2a.

  DOI：

  10.1021/np000065f

文献信息

• Efficient, Highly Enantioselective Synthesis of Selina-1,3,7(11)-trien-8-one, a Major Component of the Essential Oil of <i>Eugenia </i><i>u</i><i>niflora</i>
  作者：Alice Kanazawa、Amaury Patin、Andrew E. Greene

  DOI：10.1021/np000065f

  日期：2000.9.1

  The first synthesis of selina-1,3,7(11)-trien-8-one (1), a major constituent of the essential oil from the leaves of Eugenia uniflora, has been accomplished, with excellent stereo- and regiocontrol, in eight steps and in 12% overall yield from the known octalone derivative 2a.