(1S,7R)-4-oxa-7,11,11-trimethylbicyclo<5.4.0>undecan-3-one | 150669-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,7R)-4-oxa-7,11,11-trimethylbicyclo<5.4.0>undecan-3-one
• 英文别名: 4-Oxa-7,11,11-trimethylbicyclo-(5.4.0)undecan-3-one；(5aS,9aR)-6,6,9a-trimethyl-2,5,5a,7,8,9-hexahydro-1H-benzo[d]oxepin-4-one
• CAS: 150669-61-7
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: CMIIIOPFYNCZPR-GXFFZTMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (-)-(4aR,8aR)-3,4,4a,5,6,7,8,8a-octahydro-4a,8,8-trimethylnaphthalene-2(1H)-one 在 过氧乙酸 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 144.0h， 以50 mg的产率得到(1S,7R)-4-oxa-7,11,11-trimethylbicyclo<5.4.0>undecan-3-one
  参考文献：
  名称：

  New lactones from tobacco

  摘要：

  Thirteen lactones (1-13) have been isolated from an extract of sun-cured leaves of Greek tobacco by using HPLC methods. All but four of these (1-9) are new natural products. They have been identified as 3-(4-methyl-1-pentyl)-2-buten-4-olide (1), 3-isopropyl-2-penten-4-olide (2),3-ethyl-4-methyl-2-penten-4-olide (3), 4-methyl-3-(3-oxo-1-butyl)-2-penten-4-olide (4), 3-methyl-7-oxo-2-octen-4-olide (5), 4-(5-methyl-2-furyl)pentan-4-olide (6), (3R*,4R*,7R*)-3,7-epoxy-4,8-dimethyl-8-nonen-4-olide (7), 3-isopropyl-2,4-pentadien-5-olide (8), and (1S,7R)-4-oxa-7,11,11-trimethylbicyclo[5.4.0]undecan-3-one (9) by spectral methods, 2D NMR being a helpful tool. The syntheses of two of the lactones (1 and 9) are reported, and the plausible biogenesis of the new lactones is discussed. (Z)-6-Nonen-4-olide (10) and 5-methyl-4-hexanolide (11), now also isolated, are new to tobacco, while two 3-methyl-4-pentanolides (12 and 13), previously known as tobacco constituents, have now been identified as the 3R,4R- and 3R,4S-isomers by comparison of their optical rotations and spectral data with those of corresponding synthetic samples.

  DOI：

  10.1021/jf00035a052

文献信息

• New lactones from tobacco
  作者：Tore. Pettersson、Ann Marie. Eklund、Inger. Wahlberg

  DOI：10.1021/jf00035a052

  日期：1993.11

  Thirteen lactones (1-13) have been isolated from an extract of sun-cured leaves of Greek tobacco by using HPLC methods. All but four of these (1-9) are new natural products. They have been identified as 3-(4-methyl-1-pentyl)-2-buten-4-olide (1), 3-isopropyl-2-penten-4-olide (2),3-ethyl-4-methyl-2-penten-4-olide (3), 4-methyl-3-(3-oxo-1-butyl)-2-penten-4-olide (4), 3-methyl-7-oxo-2-octen-4-olide (5), 4-(5-methyl-2-furyl)pentan-4-olide (6), (3R*,4R*,7R*)-3,7-epoxy-4,8-dimethyl-8-nonen-4-olide (7), 3-isopropyl-2,4-pentadien-5-olide (8), and (1S,7R)-4-oxa-7,11,11-trimethylbicyclo[5.4.0]undecan-3-one (9) by spectral methods, 2D NMR being a helpful tool. The syntheses of two of the lactones (1 and 9) are reported, and the plausible biogenesis of the new lactones is discussed. (Z)-6-Nonen-4-olide (10) and 5-methyl-4-hexanolide (11), now also isolated, are new to tobacco, while two 3-methyl-4-pentanolides (12 and 13), previously known as tobacco constituents, have now been identified as the 3R,4R- and 3R,4S-isomers by comparison of their optical rotations and spectral data with those of corresponding synthetic samples.