N-[(Z,3R,4R,5R)-3,5-dimethyl-6-oxo-4-triethylsilyloxyhex-1-enyl]-N-methylformamide | 473759-03-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: N-[(Z,3R,4R,5R)-3,5-dimethyl-6-oxo-4-triethylsilyloxyhex-1-enyl]-N-methylformamide
• CAS: 473759-03-4
• 化学式: C₁₆H₃₁NO₃Si
• 分子量: 313.513
• InChiKey: QVLXRFJGPAPFNK-JGDCGQPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(Z,3R,4R,5R)-3,5-dimethyl-6-oxo-4-triethylsilyloxyhex-1-enyl]-N-methylformamide 在 咪唑 、 正丁基锂 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 [Ph₃P*CuH]6 、 水 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 15.0h， 生成 Isobutyric acid (Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodec-11-enyl ester
  参考文献：
  名称：

  Studies in marine macrolide synthesis: stereocontrolled synthesis of a C21–C34 subunit of the aplyronines

  摘要：

  The C21-C34 subunit 27 of the aplyronines, containing eight stereocentres and a terminal N-methyl-N-vinylformamide moiety, was prepared using the Horner-Wadsworth-Emmons coupling of beta-ketophosphonate 5 with aldehyde 19. The two stereotetrad sequences were constructed by chiral ketone aldol reactions, while the N-methyl-N-vinylformamide was introduced using a novel Wittig olefination. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01217-0
• 作为产物：
  描述：

  N-[(Z,3R,4R,5S)-6-hydroxy-3,5-dimethyl-4-triethylsilyloxyhex-1-enyl]-N-methylformamide 在 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到N-[(Z,3R,4R,5R)-3,5-dimethyl-6-oxo-4-triethylsilyloxyhex-1-enyl]-N-methylformamide
  参考文献：
  名称：

  Studies in marine macrolide synthesis: stereocontrolled synthesis of a C21–C34 subunit of the aplyronines

  摘要：

  The C21-C34 subunit 27 of the aplyronines, containing eight stereocentres and a terminal N-methyl-N-vinylformamide moiety, was prepared using the Horner-Wadsworth-Emmons coupling of beta-ketophosphonate 5 with aldehyde 19. The two stereotetrad sequences were constructed by chiral ketone aldol reactions, while the N-methyl-N-vinylformamide was introduced using a novel Wittig olefination. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01217-0

文献信息

• Studies in marine macrolide synthesis: stereocontrolled synthesis of a C21–C34 subunit of the aplyronines
  作者：Ian Paterson、Simon B Blakey、Cameron J Cowden

  DOI：10.1016/s0040-4039(02)01217-0

  日期：2002.8

  The C21-C34 subunit 27 of the aplyronines, containing eight stereocentres and a terminal N-methyl-N-vinylformamide moiety, was prepared using the Horner-Wadsworth-Emmons coupling of beta-ketophosphonate 5 with aldehyde 19. The two stereotetrad sequences were constructed by chiral ketone aldol reactions, while the N-methyl-N-vinylformamide was introduced using a novel Wittig olefination. (C) 2002 Elsevier Science Ltd. All rights reserved.