(1S,4S,6S)-6-but-3-enyl-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptan-2-one | 869305-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1S,4S,6S)-6-but-3-enyl-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptan-2-one
• CAS: 869305-98-6
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: HADIVGOOLNKTGT-BNOWGMLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,4S,6S)-6-but-3-enyl-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptan-2-one 在 amberlyst-15 、 氨 、 氧气 、 lithium 、 对甲苯磺酸 、 copper(l) chloride 、 palladium dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 45.0h， 生成 (1S,2R,4S)-4-Isopropenyl-2-(2-methyl-[1,3]dioxolan-2-yl)-2-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-cyclopentanol
  参考文献：
  名称：

  Enantiospecific first total synthesis of (+)-2β-hydroxysolanascone, the aglycone of the phytoalexin isolated from flue-cured tobacco leaves

  摘要：

  The first total synthesis of (+)-2 beta-hydroxysolanascone, the aglycone of the phytoalexin 2 beta-hydroxysolanascone-beta-glucopyranoside isolated from flue-cured tobacco leaves (N. tabacian L., OCL), and its 2,10-diepi- and 2 alpha-epimers has been accomplished, starting from the readily available monoterpene (R)-carvone. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.014
• 作为产物：
  描述：

  (S)-3-(but-3-enyl)carvone 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以85%的产率得到(1S,4S,6S)-6-but-3-enyl-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptan-2-one
  参考文献：
  名称：

  Enantiospecific total synthesis of phytoalexins, (+)-solanascone, (+)-dehydrosolanascone, and (+)-anhydro-β-rotunol

  摘要：

  Enantiospecific total synthesis of the phytoalexins, solavetivone, anhydro-beta-rotunol, solailascone, and dehydrosolanascone, starting from the readily available monoterpene, (R)-carvone has been accomplished. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.124

文献信息

• Enantiospecific total synthesis of phytoalexins, (+)-solanascone, (+)-dehydrosolanascone, and (+)-anhydro-β-rotunol
  作者：A. Srikrishna、S.S.V. Ramasastry

  DOI：10.1016/j.tetlet.2005.08.124

  日期：2005.10

  Enantiospecific total synthesis of the phytoalexins, solavetivone, anhydro-beta-rotunol, solailascone, and dehydrosolanascone, starting from the readily available monoterpene, (R)-carvone has been accomplished. (c) 2005 Elsevier Ltd. All rights reserved.
• Enantiospecific first total synthesis of (+)-2β-hydroxysolanascone, the aglycone of the phytoalexin isolated from flue-cured tobacco leaves
  作者：A. Srikrishna、S.S.V. Ramasastry

  DOI：10.1016/j.tetlet.2005.11.014

  日期：2006.1

  The first total synthesis of (+)-2 beta-hydroxysolanascone, the aglycone of the phytoalexin 2 beta-hydroxysolanascone-beta-glucopyranoside isolated from flue-cured tobacco leaves (N. tabacian L., OCL), and its 2,10-diepi- and 2 alpha-epimers has been accomplished, starting from the readily available monoterpene (R)-carvone. (c) 2005 Elsevier Ltd. All rights reserved.