| 1402588-95-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• CAS: 1402588-95-7
• 化学式: C₃₃H₄₉NO₁₂
• 分子量: 653.73
• InChiKey: JIENXMWPQFWHKH-PGYRSYBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  190.31
• 氢给体数：
  5.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  N,N-Diethyl-4,6-dihydroxy-3-methyl-2-(prop-2-en-1-yl)benzamide 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 palladium 10% on activated carbon 、 二氯苯酚溴酯 、 四丁基氟化铵 、 氢气 、 potassium carbonate 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 110.5h， 生成
  参考文献：
  名称：

  Studies toward the Unique Pederin Family Member Psymberin: Full Structure Elucidation, Two Alternative Total Syntheses, and Analogs

  摘要：

  Two synthetic approaches to psymberin have been accomplished. A highly convergent first generation synthesis led to the complete stereochemical assignment and demonstrated that psymberin and irciniastatin A are identical compounds. This synthesis featured a diastereoselective aldol coupling between the aryl fragment and a central tetrahydropyran core and a novel one-pot procedure to convert an amide, via intermediacy of a sensitive methyl imidate, to the N-acyl aminal reminiscent of psymberin. The highlights of the second generation synthesis include an efficient iridium-catalyzed enantioselective bisallylation of neopentyl glycol and a stepwise Sonogashira coupling/cycloisomerization/reduction sequence to construct the dihydroisocoumarin unit. The two synthetic avenues were achieved in 17-18 steps (longest linear sequence, similar to 14-15 isolations) from 3 fragments prepared in 7-8 (first generation) and 3-8 (second generation) steps each. This convergent approach allowed for the preparation of sufficient amounts of psymberin (similar to 0.5 g) for follow-up biological studies. Meanwhile, our highly flexible strategy enabled the design and synthesis of multiple analogs, including a psymberin pederin hybrid, termed psympederin, that proved crucial to a comprehensive understanding of the chemical biology of psymberin and related compounds that will be described in a subsequent manuscript.

  DOI：

  10.1021/ja3057612