(E)-2,3-dideuteroocta-2,7-dienyl diethyl phosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2,3-dideuteroocta-2,7-dienyl diethyl phosphate
• 英文别名: (6E)-6,7-dideuterio-8-[diethoxy(oxido)phosphaniumyl]oxyocta-1,6-diene
• 化学式: C₁₂H₂₃O₄P
• 分子量: 264.27
• InChiKey: ABTLGQUWLSTUBO-OXQSMGPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2,3-dideuteroocta-2,7-dienyl diethyl phosphate 在 Grubbs catalyst first generation 、 chromium dichloride 、 重铬酸吡啶 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2R,3S)-2-(tert-butoxycarbonylamino)-3-((S)-1,2-dideuterocyclohex-2-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)propanoic acid
  参考文献：
  名称：

  Stereoselective Synthesis of Deuterated β-Cyclohexenylserine, a Biosynthetic Intermediate of the Salinosporamides

  摘要：

  A straightforward, highly stereoselective protocol toward the synthesis of deuterium-labeled (2R,3S,4S)-beta-cyclohexenylserine has been developed. Key steps are a Nozaki-Hiyama-Kishi reaction generating the stereogenic centers and a ring-closing metathesis for the construction of the cyclohexenyl ring system. The labeled amino acid was further activated as an SNAc-ester for feeding experiments.

  DOI：

  10.1021/ol201120k
• 作为产物：
  描述：

  octa-7-en-2-yn-1-ol 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium deuteride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (E)-2,3-dideuteroocta-2,7-dienyl diethyl phosphate
  参考文献：
  名称：

  Stereoselective Synthesis of Deuterated β-Cyclohexenylserine, a Biosynthetic Intermediate of the Salinosporamides

  摘要：

  A straightforward, highly stereoselective protocol toward the synthesis of deuterium-labeled (2R,3S,4S)-beta-cyclohexenylserine has been developed. Key steps are a Nozaki-Hiyama-Kishi reaction generating the stereogenic centers and a ring-closing metathesis for the construction of the cyclohexenyl ring system. The labeled amino acid was further activated as an SNAc-ester for feeding experiments.

  DOI：

  10.1021/ol201120k

文献信息

• Stereoselective Synthesis of Deuterated β-Cyclohexenylserine, a Biosynthetic Intermediate of the Salinosporamides
  作者：Jan Deska、Saskia Hähn、Uli Kazmaier

  DOI：10.1021/ol201120k

  日期：2011.6.17

  A straightforward, highly stereoselective protocol toward the synthesis of deuterium-labeled (2R,3S,4S)-beta-cyclohexenylserine has been developed. Key steps are a Nozaki-Hiyama-Kishi reaction generating the stereogenic centers and a ring-closing metathesis for the construction of the cyclohexenyl ring system. The labeled amino acid was further activated as an SNAc-ester for feeding experiments.