(4R,5S)-5-[(E)-8-(2-hexyl-1,3-benzodioxol-2-yl)oct-1-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde | 1221741-33-8

• 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: (4R,5S)-5-[(E)-8-(2-hexyl-1,3-benzodioxol-2-yl)oct-1-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 1221741-33-8
• 化学式: C₂₇H₄₀O₅
• 分子量: 444.612
• InChiKey: RKMHUZJERZMQEE-XYPGREEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5S)-5-[(E)-8-(2-hexyl-1,3-benzodioxol-2-yl)oct-1-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 、 (1S,2R,5S,8R)-5,8,11,11-tetramethyl-3-oxa-6-aza-tricyclo[6.2.1.0^2,7]undec-6-en-4-one 在 双(三甲基硅烷基)氨基钾 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 、 (1S,2R,5S,8R)-5-[(R)-[(4S,5S)-5-[(E)-8-(2-hexyl-1,3-benzodioxol-2-yl)oct-1-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-5,8,11,11-tetramethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one
  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)-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

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.