7-methoxymethoxy-2,2-dimethyl-5-(2-oxopropyl)-4H-benzo[d][1,3]dioxin-4-one | 1301247-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 7-methoxymethoxy-2,2-dimethyl-5-(2-oxopropyl)-4H-benzo[d][1,3]dioxin-4-one
• 英文别名: 7-(methoxymethoxy)-2,2-dimethyl-5-(2-oxopropyl)-4H-benzo[d][1,3]dioxin-4-one；7-(methoxymethoxy)-2,2-dimethyl-5-(2-oxopropyl)-1,3-benzodioxin-4-one
• CAS: 1301247-72-2
• 化学式: C₁₅H₁₈O₆
• 分子量: 294.304
• InChiKey: ASJLGXAYFODVDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 7-methoxymethoxy-2,2-dimethyl-5-(2-oxopropyl)-4H-benzo[d][1,3]dioxin-4-one 在 三苯胺 、 lithium hexamethyldisilazane 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 7-(methoxymethoxy)-2,2-dimethyl-5-(2-trimethylsilyloxyprop-1-enyl)-1,3-benzodioxin-4-one
  参考文献：
  名称：

  Synthesis of the Purported ent-Pochonin J Structure Featuring a Stereoselective Oxocarbenium Allylation

  摘要：

  The synthesis of the alleged natural product pochonin J is presented. Key steps of this convergent synthesis include a chemoselective Wacker oxidation, and an Evans' anti-reduction of the resulting ketone. Upon ozonolysis, this intermediate undergoes a 6-exo-trig cyclization to give a hemiketal intermediate, the key oxocarbenium precursor. The construction of the alpha-C-glycoside subunit is highlighted by a mismatched oxocarbenium cation formation/allylation sequence. An olefin metathesis afforded the 14-membered macrolactone, and final oxidation provided the "desired" compound that does not spectroscopically correlate to the initially described natural product.

  DOI：

  10.1021/jo200332d
• 作为产物：
  描述：

  2,4,6-三羟基苯甲酸 在 吡啶 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 氯化亚砜 、 氧气 、 potassium carbonate 、 cesium fluoride 、 copper(l) chloride 、 palladium dichloride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 40.0 ℃ 、101.33 kPa 条件下， 反应 66.0h， 生成 7-methoxymethoxy-2,2-dimethyl-5-(2-oxopropyl)-4H-benzo[d][1,3]dioxin-4-one
  参考文献：
  名称：

  Synthesis of the Purported ent-Pochonin J Structure Featuring a Stereoselective Oxocarbenium Allylation

  摘要：

  The synthesis of the alleged natural product pochonin J is presented. Key steps of this convergent synthesis include a chemoselective Wacker oxidation, and an Evans' anti-reduction of the resulting ketone. Upon ozonolysis, this intermediate undergoes a 6-exo-trig cyclization to give a hemiketal intermediate, the key oxocarbenium precursor. The construction of the alpha-C-glycoside subunit is highlighted by a mismatched oxocarbenium cation formation/allylation sequence. An olefin metathesis afforded the 14-membered macrolactone, and final oxidation provided the "desired" compound that does not spectroscopically correlate to the initially described natural product.

  DOI：

  10.1021/jo200332d

文献信息

• Synthesis of the Purported <i>ent</i>-Pochonin J Structure Featuring a Stereoselective Oxocarbenium Allylation
  作者：Dionicio Martinez-Solorio、Kenneth A. Belmore、Michael P. Jennings

  DOI：10.1021/jo200332d

  日期：2011.5.20

  The synthesis of the alleged natural product pochonin J is presented. Key steps of this convergent synthesis include a chemoselective Wacker oxidation, and an Evans' anti-reduction of the resulting ketone. Upon ozonolysis, this intermediate undergoes a 6-exo-trig cyclization to give a hemiketal intermediate, the key oxocarbenium precursor. The construction of the alpha-C-glycoside subunit is highlighted by a mismatched oxocarbenium cation formation/allylation sequence. An olefin metathesis afforded the 14-membered macrolactone, and final oxidation provided the "desired" compound that does not spectroscopically correlate to the initially described natural product.