cis-12a-hydroxymunduserone | 66280-24-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: cis-12a-hydroxymunduserone
• 英文别名: (6aR,12aR)-12a-hydroxy-2,3,9-trimethoxy-6,6a-dihydrochromeno[3,4-b]chromen-12-one
• CAS: 66280-24-8
• 化学式: C₁₉H₁₈O₇
• 分子量: 358.348
• InChiKey: APAWOEBSLLGWDF-IEBWSBKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  cis-12a-hydroxymunduserone 在 溶剂黄146 、 锌 作用下， 反应 0.75h， 以71%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.