(4S,5S,11S)-5-[dimethyl(prop-2-enyl)silyl]oxy-6-methylidene-3-oxa-1-azatricyclo[5.3.1.04,11]undec-7-en-2-one | 905269-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5S,11S)-5-[dimethyl(prop-2-enyl)silyl]oxy-6-methylidene-3-oxa-1-azatricyclo[5.3.1.04,11]undec-7-en-2-one
• CAS: 905269-00-3
• 化学式: C₁₅H₂₁NO₃Si
• 分子量: 291.422
• InChiKey: MBSMNUWFOFICNS-IHRRRGAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5S,11S)-5-[dimethyl(prop-2-enyl)silyl]oxy-6-methylidene-3-oxa-1-azatricyclo[5.3.1.04,11]undec-7-en-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 (4R,11S)-6-ethenyl-3-oxa-1-azatricyclo[5.3.1.04,11]undeca-5,7-dien-2-one
  参考文献：
  名称：

  Stereoselective Total Synthesis of (+)-Streptazolin by Using a Temporary Silicon-Tethered RCM Strategy

  摘要：

  [GRAPHICS]A stereoselective total synthesis of (+)-streptazolin 1 was accomplished starting from readily available aminocyclopentenol (-)-7. The synthetic sequence highlights an intramolecular aldol condensation strategy to construct the piperidine core and a silicon-tethered ring-closing metathesis strategy to install the Z exocyclic ethylidene side chain of streptazolin. Separate protodesilylation and Tamao oxidation of a common intermediate 32 afforded streptazolin and the precursor for 13-hydroxystreptazolin. The overall yield for (+)-streptazolin 1 from aminocyclopentenol (-)-7 was 4.8% for a total of 16 steps.

  DOI：

  10.1021/jo060555y
• 作为产物：
  描述：

  ethyl (1S,2S,4R)-5-methylidene-3-oxa-10-azatricyclo[4.4.0.02,4]dec-6-ene-10-carboxylate 在 4-二甲氨基吡啶 、 sodium methylate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 (4S,5S,11S)-5-[dimethyl(prop-2-enyl)silyl]oxy-6-methylidene-3-oxa-1-azatricyclo[5.3.1.04,11]undec-7-en-2-one
  参考文献：
  名称：

  Stereoselective Total Synthesis of (+)-Streptazolin by Using a Temporary Silicon-Tethered RCM Strategy

  摘要：

  [GRAPHICS]A stereoselective total synthesis of (+)-streptazolin 1 was accomplished starting from readily available aminocyclopentenol (-)-7. The synthetic sequence highlights an intramolecular aldol condensation strategy to construct the piperidine core and a silicon-tethered ring-closing metathesis strategy to install the Z exocyclic ethylidene side chain of streptazolin. Separate protodesilylation and Tamao oxidation of a common intermediate 32 afforded streptazolin and the precursor for 13-hydroxystreptazolin. The overall yield for (+)-streptazolin 1 from aminocyclopentenol (-)-7 was 4.8% for a total of 16 steps.

  DOI：

  10.1021/jo060555y

文献信息

• Stereoselective Total Synthesis of (+)-Streptazolin by Using a Temporary Silicon-Tethered RCM Strategy
  作者：Fangzheng Li、Marvin J. Miller

  DOI：10.1021/jo060555y

  日期：2006.7.1

  [GRAPHICS]A stereoselective total synthesis of (+)-streptazolin 1 was accomplished starting from readily available aminocyclopentenol (-)-7. The synthetic sequence highlights an intramolecular aldol condensation strategy to construct the piperidine core and a silicon-tethered ring-closing metathesis strategy to install the Z exocyclic ethylidene side chain of streptazolin. Separate protodesilylation and Tamao oxidation of a common intermediate 32 afforded streptazolin and the precursor for 13-hydroxystreptazolin. The overall yield for (+)-streptazolin 1 from aminocyclopentenol (-)-7 was 4.8% for a total of 16 steps.