2-methyl-2-(5-hydroxyl-6-phenylsulfonyl-4,8-dimethyl-3E,7E-nonadienyl)-1,3-dioxolane | 215313-00-1

• 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-2-(5-hydroxyl-6-phenylsulfonyl-4,8-dimethyl-3E,7E-nonadienyl)-1,3-dioxolane
• 英文别名: (6E)-4-(benzenesulfonyl)-2,6-dimethyl-9-(2-methyl-1,3-dioxolan-2-yl)nona-2,6-dien-5-ol
• CAS: 215313-00-1
• 化学式: C₂₁H₃₀O₅S
• 分子量: 394.532
• InChiKey: ZZISOGBVFFHUKW-RQZCQDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-2-(5-hydroxyl-6-phenylsulfonyl-4,8-dimethyl-3E,7E-nonadienyl)-1,3-dioxolane 在 吡啶 、 lithium 、 乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 生成 2-methyl-2-(5-acetoxy-4,8-dimethyl-3E,7E-nonadienyl)-1,3-dioxolane
  参考文献：
  名称：

  First Total Synthesis of (±)-13-Hydroxyneocembrene

  摘要：

  AbstractFirst total synthesis of (±)‐13‐hydroxyneocembrene (1), starting from 6‐methyl‐5‐hepten‐2‐one (6) and geraniol (7), is described. The key steps are (i) the addition of sulfur‐stabilized carbanion 12 to aldehyde 9, (ii) the synthesis of 18 by using phase‐transfer catalyzed coupling reaction, and (iii) low‐valent titanium‐induced intramolecular coupling of oxo aldehyde 3 to afford the target molecule after the final deprotection.

  DOI：

  10.1002/jccs.199900082
• 作为产物：
  描述：

  3-methyl-1-(phenylsulfonyl)but-2-ene 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以85%的产率得到2-methyl-2-(5-hydroxyl-6-phenylsulfonyl-4,8-dimethyl-3E,7E-nonadienyl)-1,3-dioxolane
  参考文献：
  名称：

  First Total Synthesis of (±)-13-Hydroxyneocembrene

  摘要：

  AbstractFirst total synthesis of (±)‐13‐hydroxyneocembrene (1), starting from 6‐methyl‐5‐hepten‐2‐one (6) and geraniol (7), is described. The key steps are (i) the addition of sulfur‐stabilized carbanion 12 to aldehyde 9, (ii) the synthesis of 18 by using phase‐transfer catalyzed coupling reaction, and (iii) low‐valent titanium‐induced intramolecular coupling of oxo aldehyde 3 to afford the target molecule after the final deprotection.

  DOI：

  10.1002/jccs.199900082

文献信息

• First Total Synthesis of (±)-13-Hydroxyneocembrene
  作者：Yacheng Xing、Wen Cen、Jiong Lan、Ying Li、Yulin Li

  DOI：10.1002/jccs.199900082

  日期：1999.8

  AbstractFirst total synthesis of (±)‐13‐hydroxyneocembrene (1), starting from 6‐methyl‐5‐hepten‐2‐one (6) and geraniol (7), is described. The key steps are (i) the addition of sulfur‐stabilized carbanion 12 to aldehyde 9, (ii) the synthesis of 18 by using phase‐transfer catalyzed coupling reaction, and (iii) low‐valent titanium‐induced intramolecular coupling of oxo aldehyde 3 to afford the target molecule after the final deprotection.