ethyl N-[(1S,2S,5S)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl]-N-(3-oxopropyl)carbamate | 1025805-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: ethyl N-[(1S,2S,5S)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl]-N-(3-oxopropyl)carbamate
• CAS: 1025805-77-9
• 化学式: C₁₁H₁₅NO₅
• 分子量: 241.244
• InChiKey: SQODNKHKZWVENO-UJNFCWOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 ethyl (1S,2S,4R)-5-methylidene-3-oxa-10-azatricyclo[4.4.0.02,4]dec-6-ene-10-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,4R,5R)-4-hydroxy-6-oxabicyclo[3.1.0]hexan-2-yl]-N-(3-hydroxypropyl)carbamate 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,8S,9S)-2-(carboethoxy)-8,9-epoxy-2-azabicyclo[4.3.0]non-5-ol-7-one 、 ethyl N-[(1S,2S,5S)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl]-N-(3-oxopropyl)carbamate
  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.