(3S,4R)-4-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2-dimethyl-6-nitrochroman-3-ol | 1353562-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (3S,4R)-4-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2-dimethyl-6-nitrochroman-3-ol
• 英文别名: (3S,4R)-4-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2-dimethyl-6-nitro-3,4-dihydrochromen-3-ol
• CAS: 1353562-46-5
• 化学式: C₂₂H₂₇N₃O₅
• 分子量: 413.473
• InChiKey: RAWCSRCCGBIDBU-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  91
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-nitro-2,2-dimethyl chromene 在 aluminum oxide 、 sodium hypochlorite 、 sodium phosphate dibasic dodecahydrate 、 Jacobsen's catalyst 作用下， 以 二氯甲烷 、 正丁醇 为溶剂， 反应 0.2h， 生成 (3S,4R)-4-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2-dimethyl-6-nitrochroman-3-ol
  参考文献：
  名称：

  Stereoselective synthesis of (3S,4R)- and (3R,4S)-4-(N-substituted-amino)-2,2-dimethyl-6-nitrochroman-3-ols via the microwave assisted regioselective ring opening of epoxides in the presence of neutral alumina

  摘要：

  With the aim of discovering new molecules with potassium channel activating properties, we have designed and synthesized derivatives with structural similarity to cromakalim, an important molecule which shows specific affinity toward potassium channels, based on previous structure-activity investigations by applying different C-4 substitutions. This has been accomplished by using a stereoselective Jac. obsen epoxidation and microwave assisted regioselective epoxide opening with neutral alumina as the key reactions. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.002

文献信息

• Stereoselective synthesis of (3S,4R)- and (3R,4S)-4-(N-substituted-amino)-2,2-dimethyl-6-nitrochroman-3-ols via the microwave assisted regioselective ring opening of epoxides in the presence of neutral alumina
  作者：Li-juan Meng、B.V.D. Vijaykumar、Hua Zuo、Zhu-Bo Li、Gautam Dupati、Kiwan Jang、Dong-Soo Shin

  DOI：10.1016/j.tetasy.2012.07.002

  日期：2012.7

  With the aim of discovering new molecules with potassium channel activating properties, we have designed and synthesized derivatives with structural similarity to cromakalim, an important molecule which shows specific affinity toward potassium channels, based on previous structure-activity investigations by applying different C-4 substitutions. This has been accomplished by using a stereoselective Jac. obsen epoxidation and microwave assisted regioselective epoxide opening with neutral alumina as the key reactions. (c) 2012 Elsevier Ltd. All rights reserved.