(6S,7S,7aS)-6-Acetoxy-7-hydroxy-5-methylene-2,3,5,6,7,7a-hexahydro-[1]pyrindine-1-carboxylic acid ethyl ester | 905268-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (6S,7S,7aS)-6-Acetoxy-7-hydroxy-5-methylene-2,3,5,6,7,7a-hexahydro-[1]pyrindine-1-carboxylic acid ethyl ester
• 英文别名: ethyl (6S,7S,7aS)-6-acetyloxy-7-hydroxy-5-methylidene-3,6,7,7a-tetrahydro-2H-cyclopenta[b]pyridine-1-carboxylate
• CAS: 905268-98-6
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: UVHGWOYJMFFETK-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6S,7S,7aS)-6-Acetoxy-7-hydroxy-5-methylene-2,3,5,6,7,7a-hexahydro-[1]pyrindine-1-carboxylic acid ethyl ester 在 甲醇 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 ethyl (6S,7S,7aS)-7-(2,2-dimethylpropanoyloxy)-6-[dimethyl(prop-2-enyl)silyl]oxy-5-methylidene-3,6,7,7a-tetrahydro-2H-cyclopenta[b]pyridine-1-carboxylate
  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 N-[(1S,2S,5S)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl]-N-(3-oxopropyl)carbamate 在 aluminum oxide 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 9.5h， 生成 (6S,7S,7aS)-6-Acetoxy-7-hydroxy-5-methylene-2,3,5,6,7,7a-hexahydro-[1]pyrindine-1-carboxylic acid ethyl ester
  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