Epoxy macrocycle | 1301247-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Epoxy macrocycle
• 英文别名: (1S,3R,5R,14S,16R,17S)-8,10,17-tris(methoxymethoxy)-14-methyl-4,13,20-trioxatetracyclo[14.3.1.03,5.06,11]icosa-6(11),7,9-trien-12-one
• CAS: 1301247-94-8
• 化学式: C₂₄H₃₄O₁₀
• 分子量: 482.528
• InChiKey: MRZHVIFEAYXDAB-IXAHVGERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Epoxy macrocycle 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以70%的产率得到3-hydroxy-7,9,16-tris(methoxymethoxy)-13-methyl-12,19-dioxa-tricyclo-[13.3.1.0(5,10)]nonadeca-5,7,9-trien-11-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：

  在 四丁基碘化铵 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 Epoxy macrocycle
  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