(-)-(1E,3S)-5-((acetyloxy)methyl)-1-((1R)-1-((benzylamino)sulfonyl)ethyl)-2-methyl-3-((1S)-1-phenylethoxy)hexa-1,5-dien-1-yl benzoate | 872321-43-2

• 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: (-)-(1E,3S)-5-((acetyloxy)methyl)-1-((1R)-1-((benzylamino)sulfonyl)ethyl)-2-methyl-3-((1S)-1-phenylethoxy)hexa-1,5-dien-1-yl benzoate
• 英文别名: [(2S,3E,5S)-7-(acetyloxymethyl)-2-(benzylsulfamoyl)-4-methyl-5-[(1S)-1-phenylethoxy]octa-3,7-dien-3-yl] benzoate
• CAS: 872321-43-2
• 化学式: C₃₄H₃₉NO₇S
• 分子量: 605.752
• InChiKey: OZEKSYHVUVAQDY-WJBUACPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (-)-(1E,3S)-5-((acetyloxy)methyl)-1-((1R)-1-((benzylamino)sulfonyl)ethyl)-2-methyl-3-((1S)-1-phenylethoxy)hexa-1,5-dien-1-yl benzoate 在 四(三苯基膦)钯 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以79%的产率得到(-)-(6S,7E,9R)-2-benzyl-7,9-dimethyl-4-methylene-1,1-dioxido-6-((1S)-1-phenylethoxy)-2,3,4,5,6,9-hexahydro-1,2-thiazonin-8-yl benzoate
  参考文献：
  名称：

  Sulfur dioxide mediated one-pot, four-component synthesis of polyfunctional sulfones and sulfonamides, including medium-ring cyclic derivatives

  摘要：

  In previous papers (Synthesis 2002, 232 and J. Org. Chem. 2004, 69, 6413), we have shown that the hetero-Diels-Alder addition of sulfur dioxide to 1-oxy or 1,3-dioxy- 1,3-dienes generates zwitterions that add to enoxysilanes or allylsilanes giving silyl sulfinates that can be converted in the same pot into polyfunctional sulfones, sulfonamides or sulfonic esters. We are presenting further applications of this method, including the synthesis of new medium-size heterocyclic systems of the type tetrahydro-2H-thiocines and hexahydro-1,2-thiazonine. (c) 2005 Elsevier Ltd, All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.067
• 作为产物：
  描述：

  (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-ol benzoate 在 吡啶 、 N-氯代丁二酰亚胺 、 二氧化硫 、 [双(三氟甲磺酰基)氨基]三甲基硅烷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 23.0h， 生成 (-)-(1E,3S)-5-((acetyloxy)methyl)-1-((1R)-1-((benzylamino)sulfonyl)ethyl)-2-methyl-3-((1S)-1-phenylethoxy)hexa-1,5-dien-1-yl benzoate
  参考文献：
  名称：

  Sulfur dioxide mediated one-pot, four-component synthesis of polyfunctional sulfones and sulfonamides, including medium-ring cyclic derivatives

  摘要：

  In previous papers (Synthesis 2002, 232 and J. Org. Chem. 2004, 69, 6413), we have shown that the hetero-Diels-Alder addition of sulfur dioxide to 1-oxy or 1,3-dioxy- 1,3-dienes generates zwitterions that add to enoxysilanes or allylsilanes giving silyl sulfinates that can be converted in the same pot into polyfunctional sulfones, sulfonamides or sulfonic esters. We are presenting further applications of this method, including the synthesis of new medium-size heterocyclic systems of the type tetrahydro-2H-thiocines and hexahydro-1,2-thiazonine. (c) 2005 Elsevier Ltd, All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.067