(4aS,6R,8R,8aS)-4a,8-dihydroxy-4,8a-dimethyl-6-prop-1-en-2-yl-5,6,7,8-tetrahydro-1H-naphthalen-2-one | 344797-40-6

• 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: (4aS,6R,8R,8aS)-4a,8-dihydroxy-4,8a-dimethyl-6-prop-1-en-2-yl-5,6,7,8-tetrahydro-1H-naphthalen-2-one
• CAS: 344797-40-6
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: RMGCLLDEBWTTDJ-RZFFKMDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  manganese triacetate 、 (4aS,6R,8R,8aS)-4a,8-dihydroxy-4,8a-dimethyl-6-prop-1-en-2-yl-5,6,7,8-tetrahydro-1H-naphthalen-2-one 以 苯 为溶剂， 以53%的产率得到[(1R,4aS,6R,8R,8aR)-4a,8-dihydroxy-4,8a-dimethyl-2-oxo-6-prop-1-en-2-yl-5,6,7,8-tetrahydro-1H-naphthalen-1-yl] acetate
  参考文献：
  名称：

  天然二氢金呋喃呋喃倍半萜类化合物（-）-异celbicol的不对称全合成

  摘要：

  描述了从光学活性的9-氧代-10- epi - α-香芹酮（8）开始的（-）-异氟杀虫醇（一种琼脂呋喃基团的天然倍半萜烯多元醇）的第一对映选择性全合成。

  DOI：

  10.1016/s0040-4039(01)00810-3
• 作为产物：
  描述：

  hydroxycarvone 在 亚磷酸三苯酯 、 氢氧化钾 、 sodium tetrahydroborate 、 正丁基锂 、 三氟化硼乙醚 、 D-苯丙氨酸 、 D(+)-10-樟脑磺酸 、 potassium carbonate 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 191.5h， 生成 (4aS,6R,8R,8aS)-4a,8-dihydroxy-4,8a-dimethyl-6-prop-1-en-2-yl-5,6,7,8-tetrahydro-1H-naphthalen-2-one
  参考文献：
  名称：

  An enantioselective synthetic strategy toward the polyhydroxylated agarofuran

  摘要：

  This paper describes a new approach for the enantioselective syntheses of naturally occurring polyhydroxylated dihydroagarofuran sesquiterpenoids starting from (-)-carvone. Through utilizing asymmetric Robinson annulation and acetoxylation as key steps, the agarofuran skeleton was enantioselectively constructed and an oxyfunctionalized group was introduced into the C-l position. The important intermediate 23 to dihydroagarofuran was obtained in eleven steps. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00377-x

文献信息

• AN EFFICIENT AND CONVENIENT METHOD FOR THE REARRANGEMENT OF PEROXIDE COMPOUNDS
  作者：Xiaolei Gao、Gang Zhou、Yukun Guan、Weidong Z. Li、Yulin Li

  DOI：10.1081/scc-100105134

  日期：2001.1

  An alternative and convenient procedure for transformation of peroxides to hydroxy ketones by potassium carbonate is described.
• An enantioselective synthetic strategy toward the polyhydroxylated agarofuran
  作者：Gang Zhou、Xiaolei Gao、Weidong Z Li、Yulin Li

  DOI：10.1016/s0040-4039(01)00377-x

  日期：2001.4

  This paper describes a new approach for the enantioselective syntheses of naturally occurring polyhydroxylated dihydroagarofuran sesquiterpenoids starting from (-)-carvone. Through utilizing asymmetric Robinson annulation and acetoxylation as key steps, the agarofuran skeleton was enantioselectively constructed and an oxyfunctionalized group was introduced into the C-l position. The important intermediate 23 to dihydroagarofuran was obtained in eleven steps. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Asymmetric total synthesis of (−)-isocelorbicol, a natural dihydroagarofuran sesquiterpenoid
  作者：Wei-Dong Z Li、Gang Zhou、Xiaolei Gao、Yulin Li

  DOI：10.1016/s0040-4039(01)00810-3

  日期：2001.7

  The first enantioselective total synthesis of (−)-isocelorbicol, a naturally occurring sesquiterpene polyol of the agarofuran group, starting from optically active 9-oxo-10-epi-α-cyperone (8) is described.

  描述了从光学活性的9-氧代-10- epi - α-香芹酮（8）开始的（-）-异氟杀虫醇（一种琼脂呋喃基团的天然倍半萜烯多元醇）的第一对映选择性全合成。