rac-1,3,9,11-tetramethoxydibenzo[c,e]oxepin-5(7H)-one | 444647-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: rac-1,3,9,11-tetramethoxydibenzo[c,e]oxepin-5(7H)-one
• 英文别名: 1,3,9,11-tetramethoxy-7H-benzo[d][2]benzoxepin-5-one
• CAS: 444647-94-3；444584-50-3
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: VJDGVDLYMFWONR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  rac-1,3,9,11-tetramethoxydibenzo[c,e]oxepin-5(7H)-one 在 硼烷四氢呋喃络合物 、 (S)-oxazaborolidine C₁₈H₂₀NOB 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以43%的产率得到(P)-1,3,9,11-tetramethoxydibenzo[c,e]oxepin-5(7H)-one
  参考文献：
  名称：

  Atropo-Enantioselective Synthesis of the Natural Bicoumarin (+)-Isokotanin A via a Configurationally Stable Biaryl Lactone

  摘要：

  The atropo-enantioselective total synthesis of the axially chiral bicoumarin (+)-isokotanin A (1) is described. Key steps were the formation of a configurationally stable seven-membered biaryl lactone and its kinetic resolution by atroposelective ring cleavage, The previous assignment of the absolute configuration of (+)-isokotanin A (1) (and its synthetic precursors) was confirmed by quantum chemical CD calculations. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200203)2002:6<1096::aid-ejoc1096>3.0.co;2-z
• 作为产物：
  描述：

  苯甲酸,2-溴-3,5-二甲氧基-,甲基酯 在 盐酸 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 氢氧化钾 、 lithium aluminium tetrahydride 、 铜 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.5h， 生成 rac-1,3,9,11-tetramethoxydibenzo[c,e]oxepin-5(7H)-one
  参考文献：
  名称：

  Atropo-Enantioselective Synthesis of the Natural Bicoumarin (+)-Isokotanin A via a Configurationally Stable Biaryl Lactone

  摘要：

  The atropo-enantioselective total synthesis of the axially chiral bicoumarin (+)-isokotanin A (1) is described. Key steps were the formation of a configurationally stable seven-membered biaryl lactone and its kinetic resolution by atroposelective ring cleavage, The previous assignment of the absolute configuration of (+)-isokotanin A (1) (and its synthetic precursors) was confirmed by quantum chemical CD calculations. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200203)2002:6<1096::aid-ejoc1096>3.0.co;2-z

文献信息

• Atropo-Enantioselective Synthesis of the Natural Bicoumarin (+)-Isokotanin A via a Configurationally Stable Biaryl Lactone
  作者：Gerhard Bringmann、Jürgen Hinrichs、Petra Henschel、Jürgen Kraus、Karl Peters、Eva-Maria Peters

  DOI：10.1002/1099-0690(200203)2002:6<1096::aid-ejoc1096>3.0.co;2-z

  日期：2002.3

  The atropo-enantioselective total synthesis of the axially chiral bicoumarin (+)-isokotanin A (1) is described. Key steps were the formation of a configurationally stable seven-membered biaryl lactone and its kinetic resolution by atroposelective ring cleavage, The previous assignment of the absolute configuration of (+)-isokotanin A (1) (and its synthetic precursors) was confirmed by quantum chemical CD calculations. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.