2-methyl-5-(1-methylethenyl)-2-(3-oxo-1-penthyl)-1,3-cyclohexadione | 14672-23-2

• 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: 2-methyl-5-(1-methylethenyl)-2-(3-oxo-1-penthyl)-1,3-cyclohexadione
• 英文别名: 2-Methyl-2-(3-oxopentyl)-5-prop-1-en-2-ylcyclohexane-1,3-dione
• CAS: 14672-23-2
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: BXJXBFBEJYOSFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-5-(1-methylethenyl)-2-(3-oxo-1-penthyl)-1,3-cyclohexadione 在 亚磷酸三苯酯 、 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 185.5h， 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
• 作为产物：
  描述：

  (R)-Carvone 在 氢氧化钾 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 9.5h， 生成 2-methyl-5-(1-methylethenyl)-2-(3-oxo-1-penthyl)-1,3-cyclohexadione
  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

• Stereochemistry-59
  作者：Claude Agami、Franck Meynier、Catherine Puchot、Jean Guilhem、Claudine Pascard

  DOI：10.1016/s0040-4020(01)91242-6

  日期：1984.1

  sets of results give information about the mechanism of carbonyl activation by (S)-proline during asymmetric syntheses: (i) X-ray structures of two ketols produced by the proline-induced cyclization of triketones; (ii) (S)-Proline-catalyzed asymmetric dehydration of (±)-β ketols leading to optically active enones.

  两组结果给出了有关不对称合成过程中（S）-脯氨酸羰基活化机理的信息：（i）脯氨酸诱导的三酮环化生成的两种酮醇的X射线结构；（ii）（S）-脯氨酸催化的（±）-β酮醇的不对称脱水，导致旋光的烯酮。
• Synthesis of homochiral α-cyperone via enantioselective catalysis
  作者：Claude Agami、Catherine Kadouri-Puchot、Valérie Le Guen

  DOI：10.1016/s0957-4166(00)80168-8

  日期：1993.4

  The title sesquiterpene was obtained in a five-step synthesis starting from an achiral substrate: oxycarvone. Enantioselectivity is due to a phenylalanine-catalyzed intramolecular aldol reaction.
• AGAMI, C.;MEYNIER, F.;PUCHOT, C.;GUILHEM, J.;PASCARD, C., TETRAHEDRON, 1984, 40, N 6, 1031-1038
  作者：AGAMI, C.、MEYNIER, F.、PUCHOT, C.、GUILHEM, J.、PASCARD, C.

  DOI：——

  日期：——
• 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.