(2E,7E)-4,6-dihydroxynona-2,7-diene-1,9-diyl diacetate | 474005-67-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2E,7E)-4,6-dihydroxynona-2,7-diene-1,9-diyl diacetate
• 英文别名: [(2E,4R,6S,7E)-9-acetyloxy-4,6-dihydroxynona-2,7-dienyl] acetate
• CAS: 474005-67-9
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: VDDHHZRCTBJXBO-JKODOUFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E,7E)-4,6-dihydroxynona-2,7-diene-1,9-diyl diacetate 在 吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 (R,R)-DPPBA 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  A Novel Route to the F-Ring of Halichondrin B. Diastereoselection in Pd(0)-Mediated meso and C₂ Diol Desymmetrization

  摘要：

  [GRAPHICS]Both sigma and C-2 symmetric diol diacetates were synthesized via two-directional chain elongation. A palladium-mediated, ligand-controlled C-2 diol desymmetrization provided the desired tetrahydrofuran with the correct relative and absolute stereochemistries. Simple functional group manipulation led to the desired F-ring of halichondrin B. Desymmetrization of the meso substrate enantioselectively provided the diastereomer, leading to a refinement of our understanding of the transition state model.

  DOI：

  10.1021/ol026504e
• 作为产物：
  描述：

  Cis-3,5-二乙酰氧基-1-环戊烯 在 2,6-二甲基吡啶 、 二异丁基氢化铝 、 臭氧 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 6.83h， 生成 (2E,7E)-4,6-dihydroxynona-2,7-diene-1,9-diyl diacetate
  参考文献：
  名称：

  A Novel Route to the F-Ring of Halichondrin B. Diastereoselection in Pd(0)-Mediated meso and C₂ Diol Desymmetrization

  摘要：

  [GRAPHICS]Both sigma and C-2 symmetric diol diacetates were synthesized via two-directional chain elongation. A palladium-mediated, ligand-controlled C-2 diol desymmetrization provided the desired tetrahydrofuran with the correct relative and absolute stereochemistries. Simple functional group manipulation led to the desired F-ring of halichondrin B. Desymmetrization of the meso substrate enantioselectively provided the diastereomer, leading to a refinement of our understanding of the transition state model.

  DOI：

  10.1021/ol026504e

文献信息

• Stereodivergent Strategy for Neurofuran Synthesis via Palladium-Catalyzed Asymmetric Allylic Cyclization: Total Synthesis of 7-<i>epi</i>-ST-Δ⁸-10-Neurofuran
  作者：Matteo Valli、Paolo Bruno、Davide Sbarbada、Alessio Porta、Giovanni Vidari、Giuseppe Zanoni

  DOI：10.1021/jo4004647

  日期：2013.6.7

  formed in vivo in the human brain as a consequence of an increased oxidative stress, and they could be valuable biomarkers of the neuronal oxidative stress. In this paper, an enantioselective stereodivergent approach to two key neurofuran precursors, belonging to the AC and ST classes, has been developed starting from a single achiral precursor, the meso-diol 11. The absolute configuration of the THF

  神经呋喃是由于氧化应激增加而在人脑中体内形成的，它们可能是神经元氧化应激的重要生物标志物。在本文中，从单一的非手性前体中消旋二醇11开始，开发了一种对映体选择性立体发散方法，用于两种主要的AC和ST类神经呋喃。通过分别使用（S，S）-L1和（R，R）-L2配体的Pd催化的不对称烯丙基烷基化来确保THF核的绝对构型。