methyl (2Z,6E)-7-nitro-2,6-octadienoate | 124126-02-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2Z,6E)-7-nitro-2,6-octadienoate
• CAS: 124126-02-9
• 化学式: C₉H₁₃NO₄
• 分子量: 199.207
• InChiKey: UUDDOJUFDIJAEO-CGXWXWIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (2Z,6E)-7-nitro-2,6-octadienoate 在 二异丙氧基二氯化钛 、 碳酸氢钠 作用下， 以 二氯甲烷 、 甲基叔丁基醚 为溶剂， 反应 17.25h， 生成
  参考文献：
  名称：

  A Systematic Investigation of Quaternary Ammonium Ions as Asymmetric Phase-Transfer Catalysts. Synthesis of Catalyst Libraries and Evaluation of Catalyst Activity

  摘要：

  Despite over three decades of research into asymmetric phase-transfer catalysis (APTC), a fundamental understanding of the factors that affect the rate and stereoselectivity of this important process are still obscure. This paper describes the initial stages of a long-term program aimed at elucidating the physical organic foundations of APTC employing a chemoinformatic analysis of the alkylation of a protected glycine imine with libraries of enantiomerically enriched quaternary ammonium ions. The synthesis of the quaternary ammonium ions follows a diversity:oriented approach wherein the tandem inter [4 + 2]/intra[3 + 2] cycloaddition of nitroalkenes serves as the key transformation. A two-part synthetic strategy comprised of (1) preparation of enantioenriched scaffolds and (2) development of parallel synthesis procedures is described. The strategy allows for the facile introduction of four variable groups in the vicinity of a stereogenic quaternary ammonium ion. The quaternary ammonium ions exhibited a wide range of activity and to a lesser degree enantioselectivity. Catalyst activity and selectivity are rationalized in a qualitative way on the basis of the effective positive potential of the ammonium ion.

  DOI：

  10.1021/jo2005445
• 作为产物：
  描述：

  6-hydroxy-2-hexenoic acid ε-lactone 在 三氧化硫吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.33h， 生成 methyl (2Z,6E)-7-nitro-2,6-octadienoate
  参考文献：
  名称：

  A Systematic Investigation of Quaternary Ammonium Ions as Asymmetric Phase-Transfer Catalysts. Synthesis of Catalyst Libraries and Evaluation of Catalyst Activity

  摘要：

  Despite over three decades of research into asymmetric phase-transfer catalysis (APTC), a fundamental understanding of the factors that affect the rate and stereoselectivity of this important process are still obscure. This paper describes the initial stages of a long-term program aimed at elucidating the physical organic foundations of APTC employing a chemoinformatic analysis of the alkylation of a protected glycine imine with libraries of enantiomerically enriched quaternary ammonium ions. The synthesis of the quaternary ammonium ions follows a diversity:oriented approach wherein the tandem inter [4 + 2]/intra[3 + 2] cycloaddition of nitroalkenes serves as the key transformation. A two-part synthetic strategy comprised of (1) preparation of enantioenriched scaffolds and (2) development of parallel synthesis procedures is described. The strategy allows for the facile introduction of four variable groups in the vicinity of a stereogenic quaternary ammonium ion. The quaternary ammonium ions exhibited a wide range of activity and to a lesser degree enantioselectivity. Catalyst activity and selectivity are rationalized in a qualitative way on the basis of the effective positive potential of the ammonium ion.

  DOI：

  10.1021/jo2005445

文献信息

• Tandem [4 + 2]/[3 + 2] cycloadditions: facile and stereoselective construction of polycyclic frameworks
  作者：Scott E. Denmark、Young Choon Moon、C. B. W. Senanayake

  DOI：10.1021/ja00157a048

  日期：1990.1

  We describe herein a simple strategy, which expands the utility of the nitronates by intramolecularly coupling a 1,3-dipolar cycloaddition with the [4+2] process that creates them

  我们在此描述了一个简单的策略，它通过将 1,3-偶极环加成与产生它们的 [4+2] 过程进行分子内偶联来扩展硝基的效用