(4R,5R)-5-[(E)-2,6-dimethyl-1,5-heptadienyl]-4-hydroxy-2-methyl-2-cyclopentenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-5-[(E)-2,6-dimethyl-1,5-heptadienyl]-4-hydroxy-2-methyl-2-cyclopentenone
• 英文别名: (1R,5R)-litseaverticillol C；(4R,5R)-5-[(1E)-2,6-dimethylhepta-1,5-dienyl]-4-hydroxy-2-methylcyclopent-2-en-1-one
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: IRYFKBHIOJHFLA-DVFZLIDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  S-ethyl (2S,3E)-4,8-dimethyl-2-[(1S,2Z)-3-(tributylstannyl)-1-(triethylsilyloxy)-2-butenyl]-3,7-nonadienethioate 在 bis-triphenylphosphine-palladium(II) chloride 、 三(2-呋喃基)膦 噻吩-2-甲酸亚铜(I) 、 氢氟酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 (4R,5R)-5-[(E)-2,6-dimethyl-1,5-heptadienyl]-4-hydroxy-2-methyl-2-cyclopentenone
  参考文献：
  名称：

  Enantioselective Total Synthesis of Litseaverticillols A and B

  摘要：

  The first enantioselective total synthesis of the (1 R,5S)-stereoisomer of litseaverticillols A and B, anti-HIV monocyclic sesquiterpenoids isolated from a perennial shrub found in Vietnam, was accomplished in six steps from homogeranic acid by employing the Evans asymmetric aldol reaction and a microwave-promoted cyclization of a stannylated thiol ester intermediate as the C-C bond-forming steps.

  DOI：

  10.1021/ol053122a

文献信息

• Illustrating the Power of Singlet Oxygen Chemistry in a Synthetic Context: Biomimetic Syntheses of Litseaverticillols A-G, I and J and the Structural Reassignment of Litseaverticillol E
  作者：Georgios Vassilikogiannakis、Ioannis Margaros、Tamsyn Montagnon、Manolis Stratakis

  DOI：10.1002/chem.200401311

  日期：2005.10.7

  Biomimetic syntheses of the litseaverticillols A-G, I and J are reported herein. The syntheses rely heavily on the application of two different modes of reaction for photochemically generated singlet oxygen, namely, the [4+2] cycloaddition of singlet oxygen (1O2) with furans and the ene reaction of 1O2 with double bonds. The highlight of these syntheses is a one-pot cascade sequence, involving five

  本文报道了枯草麻木AG，I和J的仿生合成。合成很大程度上依赖于光化学生成的单线态氧的两种不同反应模式的应用，即单线态氧（1O2）与呋喃的[4 + 2]环加成反应和1O2与双键的烯反应。这些合成的亮点是一锅级联序列，涉及由[4 + 2]反应引发的五种合成操作，以形成功能齐全的联苯并香茅醇核心。然后使用一系列的区域选择性烯反应适当地官能化侧链。邻苯二酚E的合成（包括最初提出的结构和实际结构）都可以对该天然产物进行结构上的重新分配。
• Enantioselective Total Synthesis of Litseaverticillols A and B
  作者：Akira Morita、Shigefumi Kuwahara

  DOI：10.1021/ol053122a

  日期：2006.4.1

  The first enantioselective total synthesis of the (1 R,5S)-stereoisomer of litseaverticillols A and B, anti-HIV monocyclic sesquiterpenoids isolated from a perennial shrub found in Vietnam, was accomplished in six steps from homogeranic acid by employing the Evans asymmetric aldol reaction and a microwave-promoted cyclization of a stannylated thiol ester intermediate as the C-C bond-forming steps.