t-butyldimethylsilyl 3-(2'-t-butyldimethylsilyloxy-4'-methoxyphenyl)propanoate | 188782-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: t-butyldimethylsilyl 3-(2'-t-butyldimethylsilyloxy-4'-methoxyphenyl)propanoate
• CAS: 188782-89-0
• 化学式: C₂₂H₄₀O₄Si₂
• 分子量: 424.728
• InChiKey: TYDDRSAKDLCDHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  t-butyldimethylsilyl 3-(2'-t-butyldimethylsilyloxy-4'-methoxyphenyl)propanoate 在 草酰氯 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  Conversion of 7-methoxy-3,4-dihydro-2H-1-benzopyran-2-one into the corresponding dimethyl ortho ester

  摘要：

  7-Methoxy-3,4-dihydro-2H-1-benzopyran-2-one 2 was converted into 3-(2'-tert-butyldimethylsilyloxy-4'-methoxyphenyl)-N-Methyl-N-phenylpropanamide 25 and reaction of this with methyl trifluoromethanesulfonate, followed by reaction with sodium methoxide, gave 2,2,7-trimethoxy-2H-1-benzopyran 1a in 55% overall yield from 25. A similar methylation/methoxide sequence using 3-(2'-benzyloxy-4'-methoxyphenyl)-N-methyl-N-phenylpropanamide 18 gave a mixture which contained trimethyl 3-(2'-benzyloxy-4'-methoxyphenyl)orthopropanoate 20a and reaction of this mixture with a solution of sodium in tert-butanol gave a product in which 2,2,7-trimethoxy-2H-1-benzopyran 1a was detected, but not isolable. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00007-0
• 作为产物：
  描述：

  7-甲氧基-3,4-二氢色烯-2-酮 在 咪唑 、 氢氧化钾 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 117.5h， 生成 t-butyldimethylsilyl 3-(2'-t-butyldimethylsilyloxy-4'-methoxyphenyl)propanoate
  参考文献：
  名称：

  Conversion of 7-methoxy-3,4-dihydro-2H-1-benzopyran-2-one into the corresponding dimethyl ortho ester

  摘要：

  7-Methoxy-3,4-dihydro-2H-1-benzopyran-2-one 2 was converted into 3-(2'-tert-butyldimethylsilyloxy-4'-methoxyphenyl)-N-Methyl-N-phenylpropanamide 25 and reaction of this with methyl trifluoromethanesulfonate, followed by reaction with sodium methoxide, gave 2,2,7-trimethoxy-2H-1-benzopyran 1a in 55% overall yield from 25. A similar methylation/methoxide sequence using 3-(2'-benzyloxy-4'-methoxyphenyl)-N-methyl-N-phenylpropanamide 18 gave a mixture which contained trimethyl 3-(2'-benzyloxy-4'-methoxyphenyl)orthopropanoate 20a and reaction of this mixture with a solution of sodium in tert-butanol gave a product in which 2,2,7-trimethoxy-2H-1-benzopyran 1a was detected, but not isolable. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00007-0

文献信息

• Conversion of 7-methoxy-3,4-dihydro-2H-1-benzopyran-2-one into the corresponding dimethyl ortho ester
  作者：David G. Bourke、David J. Collins

  DOI：10.1016/s0040-4020(97)00007-0

  日期：1997.3

  7-Methoxy-3,4-dihydro-2H-1-benzopyran-2-one 2 was converted into 3-(2'-tert-butyldimethylsilyloxy-4'-methoxyphenyl)-N-Methyl-N-phenylpropanamide 25 and reaction of this with methyl trifluoromethanesulfonate, followed by reaction with sodium methoxide, gave 2,2,7-trimethoxy-2H-1-benzopyran 1a in 55% overall yield from 25. A similar methylation/methoxide sequence using 3-(2'-benzyloxy-4'-methoxyphenyl)-N-methyl-N-phenylpropanamide 18 gave a mixture which contained trimethyl 3-(2'-benzyloxy-4'-methoxyphenyl)orthopropanoate 20a and reaction of this mixture with a solution of sodium in tert-butanol gave a product in which 2,2,7-trimethoxy-2H-1-benzopyran 1a was detected, but not isolable. (C) 1997 Elsevier Science Ltd.