pergillin | 74798-20-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: pergillin
• 英文别名: 7-hydroxy-7-methyl-2-propan-2-ylidene-6,9-dihydrofuro[3,2-h]isochromen-3-one
• CAS: 74798-20-2
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: MKXDAWJZYZIEIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  pergillin 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 以80%的产率得到dihydropergillin
  参考文献：
  名称：

  Synthesis and Structural Characterization of Natural Benzofuranoids

  摘要：

  The synthesis of ustusoranes A, B, and E, pergillin, dihydropergillin, (+/-)-penicisochroman A, and (-)-brassicadiol, starting from optically active (R)-benzolactone, is described. The synthesis of ustusoranes A and E established the absolute configurations of these natural products. The synthesis of pergillin and ()-penicisochroman A led to the structural revision of aspergiones E and F. This study clearly indicates that (R)-benzolactone is a potential intermediate in the synthesis of natural benzofuranoids.

  DOI：

  10.1021/np5010483
• 作为产物：
  描述：

  7-(tert-butyldimethylsiloxymethyl)-6-(2-oxopropyl)-2-(propan-2-ylidene)benzofuran-3(2H)-one 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以85%的产率得到pergillin
  参考文献：
  名称：

  Synthesis and Structural Characterization of Natural Benzofuranoids

  摘要：

  The synthesis of ustusoranes A, B, and E, pergillin, dihydropergillin, (+/-)-penicisochroman A, and (-)-brassicadiol, starting from optically active (R)-benzolactone, is described. The synthesis of ustusoranes A and E established the absolute configurations of these natural products. The synthesis of pergillin and ()-penicisochroman A led to the structural revision of aspergiones E and F. This study clearly indicates that (R)-benzolactone is a potential intermediate in the synthesis of natural benzofuranoids.

  DOI：

  10.1021/np5010483

文献信息

• Synthesis and Structural Characterization of Natural Benzofuranoids
  作者：Kouji Kuramochi、Kazunori Tsubaki

  DOI：10.1021/np5010483

  日期：2015.5.22

  The synthesis of ustusoranes A, B, and E, pergillin, dihydropergillin, (+/-)-penicisochroman A, and (-)-brassicadiol, starting from optically active (R)-benzolactone, is described. The synthesis of ustusoranes A and E established the absolute configurations of these natural products. The synthesis of pergillin and ()-penicisochroman A led to the structural revision of aspergiones E and F. This study clearly indicates that (R)-benzolactone is a potential intermediate in the synthesis of natural benzofuranoids.