3,25-dibromo-6,22-dimethoxy-4,24-dimethyl-8,11,14,17,20-pentaoxa-tricyclo[19.4.0.02,7]pentacosa-1(25),2,4,6,21,23-hexaene | 936102-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,25-dibromo-6,22-dimethoxy-4,24-dimethyl-8,11,14,17,20-pentaoxa-tricyclo[19.4.0.02,7]pentacosa-1(25),2,4,6,21,23-hexaene
• CAS: 936102-19-1
• 化学式: C₂₄H₃₀Br₂O₇
• 分子量: 590.306
• InChiKey: LHDPJWKYHNZTQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  33.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,25-dibromo-6,22-dimethoxy-4,24-dimethyl-8,11,14,17,20-pentaoxa-tricyclo[19.4.0.02,7]pentacosa-1(25),2,4,6,21,23-hexaene 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以60%的产率得到3,25-Dibromo-4,24-bis-bromomethyl-6,22-dimethoxy-8,11,14,17,20-pentaoxa-tricyclo[19.4.0.0^2,7]pentacosa-1(25),2(7),3,5,21,23-hexaene
  参考文献：
  名称：

  2,2′-Dihydroxy-3,3′-dimethoxy-5,5′-dimethyl-6,6′-dibromo-1,1′-biphenyl: preparation, resolution, structure and biological activity

  摘要：

  The preparation and resolution of the titled conformationally stable biphenyl 1 has been performed in high chemical yield starting from creosol 2. Enantiopure biphenyls (aR)-(+)-1 and (aS)-(-)-1 were obtained by the corresponding menthylcarbonate diastereomer and successive reduction. The absolute configuration and specific rotation were correlated by X-ray analysis of the crystal structure of diastereopure menthylcarbonate (aS,1R,1'R,2S,2'S,5R,5'R)-(+)-16. Preliminary biological evaluation of both racemic enantiomers of 1 has been carried out on melanoma cell lines and significant and selective anticancer activity has been observed for the enantiomer (aS)-(-)-1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.017
• 作为产物：
  描述：

  2-甲氧基-4-甲基苯酚 在 N-溴代丁二酰亚胺(NBS) 、 methyltri(butyl)ammonium permanganate 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3,25-dibromo-6,22-dimethoxy-4,24-dimethyl-8,11,14,17,20-pentaoxa-tricyclo[19.4.0.02,7]pentacosa-1(25),2,4,6,21,23-hexaene
  参考文献：
  名称：

  2,2′-Dihydroxy-3,3′-dimethoxy-5,5′-dimethyl-6,6′-dibromo-1,1′-biphenyl: preparation, resolution, structure and biological activity

  摘要：

  The preparation and resolution of the titled conformationally stable biphenyl 1 has been performed in high chemical yield starting from creosol 2. Enantiopure biphenyls (aR)-(+)-1 and (aS)-(-)-1 were obtained by the corresponding menthylcarbonate diastereomer and successive reduction. The absolute configuration and specific rotation were correlated by X-ray analysis of the crystal structure of diastereopure menthylcarbonate (aS,1R,1'R,2S,2'S,5R,5'R)-(+)-16. Preliminary biological evaluation of both racemic enantiomers of 1 has been carried out on melanoma cell lines and significant and selective anticancer activity has been observed for the enantiomer (aS)-(-)-1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.017