(4aR,8aS)-5,8a-dimethyl-3,4,4a,8a-tetrahydro-1H-naphthalen-2-one | 294202-71-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,8aS)-5,8a-dimethyl-3,4,4a,8a-tetrahydro-1H-naphthalen-2-one
• 英文别名: (4aR,8aS)-5,8a-dimethyl-1,3,4,4a-tetrahydronaphthalen-2-one
• CAS: 294202-71-4
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: BDGWXWFZAUBBEA-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  二硫化碳 、 (4aR,8aS)-5,8a-dimethyl-3,4,4a,8a-tetrahydro-1H-naphthalen-2-one 、 碘甲烷 以68%的产率得到(4aR,8aS)-3-(bis-methylsulfanyl-methylene)-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)-N'-(5,8a-dimethyl-1,3,4,7,8,8a-hexahydro-6H-spiro[naphthalene-2,2'-[1,3]dioxolan]-6-ylidene)-4-methylbenzenesulfonohydrazide 在 3,5-二甲基吡唑 、 chromium(VI) oxide 、 甲基锂 、 溶剂黄146 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 11.25h， 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

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.