2-hexyl-2-[(7E,9S,10S)-9,10-isopropylidenedioxy-7-undecenyl-11-ol]benzo[1,3]dioxole | 1221741-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-hexyl-2-[(7E,9S,10S)-9,10-isopropylidenedioxy-7-undecenyl-11-ol]benzo[1,3]dioxole
• 英文别名: [(4S,5S)-5-[(E)-8-(2-hexyl-1,3-benzodioxol-2-yl)oct-1-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 1221741-41-8
• 化学式: C₂₇H₄₂O₅
• 分子量: 446.627
• InChiKey: GMUDPXWINMDIJN-XYPGREEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hexyl-2-[(7E,9S,10S)-9,10-isopropylidenedioxy-7-undecenyl-11-ol]benzo[1,3]dioxole 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (4R,5S)-5-[(E)-8-(2-hexyl-1,3-benzodioxol-2-yl)oct-1-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
  参考文献：
  名称：

  Total Synthesis of Sphingofungin F Based on Chiral Tricyclic Iminolactone

  摘要：

  A new, efficient synthesis of sphingofungin F has been accomplished with 10.4% overall yield in 15 steps. The salient features of the synthesis are the utilization of methyl tricyclic iminolactone 3 for the asymmetric aldol reaction as a key step to introduce two desired stereogenic centers, one-pot reaction for the synthesis of omega-hydroxyketone from epsilon-caprolactone, and an effective one-step deprotection strategy to remove all protecting groups using 0.2 N HCl.

  DOI：

  10.1021/jo100183d
• 作为产物：
  描述：

  2-hexyl-2-[(7E,9S,10S)-5-phenylsulfonyl-9,10-isopropylidenedioxy-7-undecenyl-11-ol]benzo[1,3]dioxole 在 甲醇 、 sodium amalgam 作用下， 反应 3.0h， 以90%的产率得到2-hexyl-2-[(7E,9S,10S)-9,10-isopropylidenedioxy-7-undecenyl-11-ol]benzo[1,3]dioxole
  参考文献：
  名称：

  Total Synthesis of Sphingofungin F Based on Chiral Tricyclic Iminolactone

  摘要：

  A new, efficient synthesis of sphingofungin F has been accomplished with 10.4% overall yield in 15 steps. The salient features of the synthesis are the utilization of methyl tricyclic iminolactone 3 for the asymmetric aldol reaction as a key step to introduce two desired stereogenic centers, one-pot reaction for the synthesis of omega-hydroxyketone from epsilon-caprolactone, and an effective one-step deprotection strategy to remove all protecting groups using 0.2 N HCl.

  DOI：

  10.1021/jo100183d

文献信息

• Total Synthesis of Sphingofungin F Based on Chiral Tricyclic Iminolactone
  作者：Feng-Feng Gan、Shao-Bo Yang、Yong-Chun Luo、Wan-Bang Yang、Peng-Fei Xu

  DOI：10.1021/jo100183d

  日期：2010.4.16

  A new, efficient synthesis of sphingofungin F has been accomplished with 10.4% overall yield in 15 steps. The salient features of the synthesis are the utilization of methyl tricyclic iminolactone 3 for the asymmetric aldol reaction as a key step to introduce two desired stereogenic centers, one-pot reaction for the synthesis of omega-hydroxyketone from epsilon-caprolactone, and an effective one-step deprotection strategy to remove all protecting groups using 0.2 N HCl.