(2S,4S)-2-acetyl-2-but-3-enyl-4-prop-1-en-2-ylcyclopentan-1-one | 874658-19-2

• 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: (2S,4S)-2-acetyl-2-but-3-enyl-4-prop-1-en-2-ylcyclopentan-1-one
• CAS: 874658-19-2
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: CZFOZJIJNSBULR-OCCSQVGLSA-N

物化性质

• 沸点：
  316.6±42.0 °C(Predicted)
• 密度：
  0.974±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,4S)-2-acetyl-2-but-3-enyl-4-prop-1-en-2-ylcyclopentan-1-one 在 氨 、 氧气 、 lithium 、 对甲苯磺酸 、 copper(l) chloride 、 palladium dichloride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 21.0h， 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：

  (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 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以74%的产率得到(2S,4S)-2-acetyl-2-but-3-enyl-4-prop-1-en-2-ylcyclopentan-1-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.