[(R)-[(1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-[2-[tert-butyl(dimethyl)silyl]oxy-4,5-bis(phenylmethoxy)phenyl]methyl] acetate | 247577-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(R)-[(1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-[2-[tert-butyl(dimethyl)silyl]oxy-4,5-bis(phenylmethoxy)phenyl]methyl] acetate
• CAS: 247577-70-4
• 化学式: C₄₃H₆₀O₆Si
• 分子量: 701.031
• InChiKey: INNBDJFYJWDGQA-ZNURCCPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.83
• 重原子数：
  50.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [(R)-[(1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-[2-[tert-butyl(dimethyl)silyl]oxy-4,5-bis(phenylmethoxy)phenyl]methyl] acetate 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 puupehenone
  参考文献：
  名称：

  Enantiospecific synthesis of (+)-puupehenone from (−)-sclareol and protocatechualdehyde

  摘要：

  The first enantiospecific synthesis of the antitumor and cholesteryl ester transfer protein (CETP) inhibitor (+)-puupehenone (19) from (-)-sclareol (10) and protocatechualdehyde (4) is described. The key steps of the reaction sequence are the organoselenium-induced cyclization of the mixture of regioisomers 15a-b to give 16 and 17, with complete diastereoselectivity, and the simultaneous removal of benzyl and phenylselenyl groups of 16 and 17 by treating with Raney Ni. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00305-5
• 作为产物：
  描述：

  1,2-di-O-benzyl-4-O-tert-butyldimethylsilylbenzenetriol 在 N-溴代丁二酰亚胺(NBS) 、 叔丁基锂 、 silica gel 作用下， 以 四氯化碳 、 乙醚 为溶剂， 生成 [(R)-[(1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-[2-[tert-butyl(dimethyl)silyl]oxy-4,5-bis(phenylmethoxy)phenyl]methyl] acetate
  参考文献：
  名称：

  Enantiospecific synthesis of (+)-puupehenone from (−)-sclareol and protocatechualdehyde

  摘要：

  The first enantiospecific synthesis of the antitumor and cholesteryl ester transfer protein (CETP) inhibitor (+)-puupehenone (19) from (-)-sclareol (10) and protocatechualdehyde (4) is described. The key steps of the reaction sequence are the organoselenium-induced cyclization of the mixture of regioisomers 15a-b to give 16 and 17, with complete diastereoselectivity, and the simultaneous removal of benzyl and phenylselenyl groups of 16 and 17 by treating with Raney Ni. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00305-5