3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxymethyl]-6-methyl-7-trityl-3,5-dihydro-imidazo[1,2-a]purin-9-one | 204863-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxymethyl]-6-methyl-7-trityl-3,5-dihydro-imidazo[1,2-a]purin-9-one
• 英文别名: 3-[2-[tert-butyl(dimethyl)silyl]oxyethoxymethyl]-6-methyl-7-trityl-5H-imidazo[1,2-a]purin-9-one
• CAS: 204863-93-4
• 化学式: C₃₆H₄₁N₅O₃Si
• 分子量: 619.839
• InChiKey: NZKZENPEJYDUIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  81
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxymethyl]-6-methyl-7-trityl-3,5-dihydro-imidazo[1,2-a]purin-9-one 在 溶剂黄146 作用下， 以 水 为溶剂， 以90%的产率得到3-(2-Hydroxy-ethoxymethyl)-6-methyl-7-trityl-3,5-dihydro-imidazo[1,2-a]purin-9-one
  参考文献：
  名称：

  A case of unusual sterically driven C-tritylation reaction of tricyclic analogues of acyclovir

  摘要：

  3,9-Dihydro-3-[(2-hydroxyethoxy)methyl] 6-methyl-9-oxo-5H-imidazo[1,2-a]purine (1) and its silylated derivative (2) when tritylated under conditions suitable for regioselective N-5 alkylation underwent instead C-substitution to give 7-trityl (12, 3) and 7-(4-benzhydrylphenyl) (13, 4) derivatives as major and minor products, respectively. Substrates lacking 6-Me group (5, 6) yielded 5-tritylated (10, 7) and 5,7-ditritylated (11, 8) major products and 7-tritylated (9) minor product. The regioselectivity of the reaction seems to be driven mainly by steric hindrance of the 6-Me substituent. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)83029-9
• 作为产物：
  描述：

  3-(2-羟基乙氧基甲基)-6-甲基-5H-咪唑并[1,2-a]嘌呤-9-酮 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.5h， 生成 3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxymethyl]-6-methyl-7-trityl-3,5-dihydro-imidazo[1,2-a]purin-9-one
  参考文献：
  名称：

  A case of unusual sterically driven C-tritylation reaction of tricyclic analogues of acyclovir

  摘要：

  3,9-Dihydro-3-[(2-hydroxyethoxy)methyl] 6-methyl-9-oxo-5H-imidazo[1,2-a]purine (1) and its silylated derivative (2) when tritylated under conditions suitable for regioselective N-5 alkylation underwent instead C-substitution to give 7-trityl (12, 3) and 7-(4-benzhydrylphenyl) (13, 4) derivatives as major and minor products, respectively. Substrates lacking 6-Me group (5, 6) yielded 5-tritylated (10, 7) and 5,7-ditritylated (11, 8) major products and 7-tritylated (9) minor product. The regioselectivity of the reaction seems to be driven mainly by steric hindrance of the 6-Me substituent. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)83029-9

文献信息

• A case of unusual sterically driven C-tritylation reaction of tricyclic analogues of acyclovir
  作者：Joanna Zeidler、Bożenna Golankiewicz

  DOI：10.1016/s0040-4020(98)83029-9

  日期：1998.3

  3,9-Dihydro-3-[(2-hydroxyethoxy)methyl] 6-methyl-9-oxo-5H-imidazo[1,2-a]purine (1) and its silylated derivative (2) when tritylated under conditions suitable for regioselective N-5 alkylation underwent instead C-substitution to give 7-trityl (12, 3) and 7-(4-benzhydrylphenyl) (13, 4) derivatives as major and minor products, respectively. Substrates lacking 6-Me group (5, 6) yielded 5-tritylated (10, 7) and 5,7-ditritylated (11, 8) major products and 7-tritylated (9) minor product. The regioselectivity of the reaction seems to be driven mainly by steric hindrance of the 6-Me substituent. (C) 1998 Elsevier Science Ltd. All rights reserved.