(6,7-dimethoxy-2H-chromen-4-yl)-[4-methoxy-2-(methoxymethoxy)phenyl]methanone | 1163251-95-3

• 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: (6,7-dimethoxy-2H-chromen-4-yl)-[4-methoxy-2-(methoxymethoxy)phenyl]methanone
• CAS: 1163251-95-3
• 化学式: C₂₁H₂₂O₇
• 分子量: 386.401
• InChiKey: PVYUJZROXZHDGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6,7-dimethoxy-2H-chromen-4-yl)-[4-methoxy-2-(methoxymethoxy)phenyl]methanone 在 盐酸 、 甲醇 作用下， 反应 2.0h， 以86%的产率得到(+/-)-Munduseron
  参考文献：
  名称：

  Protected Cyanohydrins in the Synthesis of Rotenoids: (±)-Munduserone and (±)-cis-12a-Hydroxymunduserone

  摘要：

  Short synthetic routes to the natural products (+/-)-munduserone 1 and (+/-)-cis-12a-hydroxymunduserone 9 from protected cyanohydrin 5 and nitrochromene 4 are described. The key coupling reaction of 4 and 5 gave under inverse addition conditions 9 (28%) and 2b (21%), while under normal addition conditions, a mixture of 9 (20%), dehydromunduserone 10 (9%), and enone 2b (10%) was obtained. (+/-)-Munduserone 1 is easily obtained from both 2b and 9 by 10% methanolic HCl (86%) and Zn/AcOH (71%) treatments, respectively.

  DOI：

  10.1021/jo900648n
• 作为产物：
  描述：

  6,7-dimethoxy-3-nitro-chromene 、 2-(4-methoxy-2-(methoxymethoxy)phenyl)-2-(trimethylsilyloxy)acetonitrile 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以21%的产率得到(6,7-dimethoxy-2H-chromen-4-yl)-[4-methoxy-2-(methoxymethoxy)phenyl]methanone
  参考文献：
  名称：

  Protected Cyanohydrins in the Synthesis of Rotenoids: (±)-Munduserone and (±)-cis-12a-Hydroxymunduserone

  摘要：

  Short synthetic routes to the natural products (+/-)-munduserone 1 and (+/-)-cis-12a-hydroxymunduserone 9 from protected cyanohydrin 5 and nitrochromene 4 are described. The key coupling reaction of 4 and 5 gave under inverse addition conditions 9 (28%) and 2b (21%), while under normal addition conditions, a mixture of 9 (20%), dehydromunduserone 10 (9%), and enone 2b (10%) was obtained. (+/-)-Munduserone 1 is easily obtained from both 2b and 9 by 10% methanolic HCl (86%) and Zn/AcOH (71%) treatments, respectively.

  DOI：

  10.1021/jo900648n

文献信息

• Protected Cyanohydrins in the Synthesis of Rotenoids: (±)-Munduserone and (±)-<i>cis</i>-12a-Hydroxymunduserone
  作者：Evin H. Granados-Covarrubias、Luis A. Maldonado

  DOI：10.1021/jo900648n

  日期：2009.7.17

  Short synthetic routes to the natural products (+/-)-munduserone 1 and (+/-)-cis-12a-hydroxymunduserone 9 from protected cyanohydrin 5 and nitrochromene 4 are described. The key coupling reaction of 4 and 5 gave under inverse addition conditions 9 (28%) and 2b (21%), while under normal addition conditions, a mixture of 9 (20%), dehydromunduserone 10 (9%), and enone 2b (10%) was obtained. (+/-)-Munduserone 1 is easily obtained from both 2b and 9 by 10% methanolic HCl (86%) and Zn/AcOH (71%) treatments, respectively.