3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diyl-O,O'-bis[5-methyl-2-(1-methylethyl)-cyclohexyl]-carbonic ester | 936102-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diyl-O,O'-bis[5-methyl-2-(1-methylethyl)-cyclohexyl]-carbonic ester
• CAS: 936102-23-7
• 化学式: C₃₈H₅₄O₈
• 分子量: 638.842
• InChiKey: MHIKINNHMNHMLE-AWAUJLNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.94
• 重原子数：
  46.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diyl-O,O'-bis[5-methyl-2-(1-methylethyl)-cyclohexyl]-carbonic ester 在 lithium aluminium tetrahydride 、 溶剂黄146 、 benzyltriethylammonium perbromide 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 (aS)-(-)-2,2'-dihydroxy-3,3'-dimethoxy-5,5'-dimethyl-6,6'-dibromo-1,1'-biphenyl
  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 methyltri(butyl)ammonium permanganate 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diyl-O,O'-bis[5-methyl-2-(1-methylethyl)-cyclohexyl]-carbonic ester
  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