2-[5-(hydroxymethyl)-2H-pyran-3-(6H)-one]-1-oxaspiro[4.5]deca-6,9-dien-8-one | 1240715-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 2-[5-(hydroxymethyl)-2H-pyran-3-(6H)-one]-1-oxaspiro[4.5]deca-6,9-dien-8-one
• CAS: 1240715-27-8
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: CCCHPNOFSQOIIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-[5-(hydroxymethyl)-2H-pyran-3-(6H)-one]-1-oxaspiro[4.5]deca-6,9-dien-8-one 、 肉豆蔻酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以38%的产率得到2-[(5,6-dihydro-5-oxo-2H-pyran-3-yl)methyl tetradecanoate]-1-oxaspiro[4.5]deca-6,9-dien-8-one
  参考文献：
  名称：

  Hypervalent iodine(III)-mediated tandem oxidative reactions: application for the synthesis of bioactive polyspirocyclohexa-2,5-dienones

  摘要：

  In 2002, we reported the first total syntheses of potent antimalarial natural products, the aculeatins, employing the concept of tandem oxidative reactions mediated by hypervalent iodine(III) reagent to access to polyspirocyclohexa-2,5-dienone cores in very concise manner. Efforts in this field have allowed to identify cyclohexa-2,5-dienone group as a new potent class of pharmacophoric group for treating malaria disease. This article sums up recent contributions devoted to the synthesis of complex and diverse polycyclic structures using the concept of tandem oxidative activations, with p-phenol as co-reactant. More recently, we have explored a variant of the new tandem oxidative reactions that employs a catalytic amount of 4-iodotoluene in the presence of mCPBA as the stoichiometric oxidant (Kita's procedure). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.135
• 作为产物：
  描述：

  (5-(4-hydroxyphenethyl)furan-2,4-diyl)dimethanol 在 4-碘甲苯 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 六氟异丙醇 为溶剂， 反应 1.0h， 以25%的产率得到2-[5-(hydroxymethyl)-2H-pyran-3-(6H)-one]-1-oxaspiro[4.5]deca-6,9-dien-8-one
  参考文献：
  名称：

  Hypervalent iodine(III)-mediated tandem oxidative reactions: application for the synthesis of bioactive polyspirocyclohexa-2,5-dienones

  摘要：

  In 2002, we reported the first total syntheses of potent antimalarial natural products, the aculeatins, employing the concept of tandem oxidative reactions mediated by hypervalent iodine(III) reagent to access to polyspirocyclohexa-2,5-dienone cores in very concise manner. Efforts in this field have allowed to identify cyclohexa-2,5-dienone group as a new potent class of pharmacophoric group for treating malaria disease. This article sums up recent contributions devoted to the synthesis of complex and diverse polycyclic structures using the concept of tandem oxidative activations, with p-phenol as co-reactant. More recently, we have explored a variant of the new tandem oxidative reactions that employs a catalytic amount of 4-iodotoluene in the presence of mCPBA as the stoichiometric oxidant (Kita's procedure). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.135