(2S,3R)-2-[[[[3,5-双(三氟甲基)苯基]氨基]硫代甲基]氨基]-N-(8Α,9S)-奎宁-9-基-3-[[(1,1-二甲基乙基)二苯基甲硅烷基]氧基]丁酰胺 | 1381859-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: (2S,3R)-2-[[[[3,5-双(三氟甲基)苯基]氨基]硫代甲基]氨基]-N-(8Α,9S)-奎宁-9-基-3-[[(1,1-二甲基乙基)二苯基甲硅烷基]氧基]丁酰胺
• 英文名称: (2S,3R)-2-{3-[3,5-bis(trifluoromethyl)phenyl]thioureido}-3-[(tert-butyldiphenylsilyl)oxy]-N-{(S)-quinolin-4-yl-[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methyl}butanamide
• 英文别名: (2S,3R)-2-(3-(3,5-Bis(trifluoromethyl)phenyl)thioureido)-3-((tert-butyldiphenylsilyl)oxy)-N-((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)butanamide；(2S,3R)-2-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]-3-[tert-butyl(diphenyl)silyl]oxy-N-[(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethyl]butanamide
• CAS: 1381859-85-3
• 化学式: C₄₈H₅₁F₆N₅O₂SSi
• 分子量: 904.107
• InChiKey: SSWZBDWQWOEADT-YXSARBTGSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.65
• 重原子数：
  63
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  tert-butyl {(2S,3R)-3-[(tert-butyldiphenylsilyl)oxy]-1-oxo-1-({(S)-quinolin-4-yl-[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methyl}amino)butan-2-yl}carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (2S,3R)-2-[[[[3,5-双(三氟甲基)苯基]氨基]硫代甲基]氨基]-N-(8Α,9S)-奎宁-9-基-3-[[(1,1-二甲基乙基)二苯基甲硅烷基]氧基]丁酰胺
  参考文献：
  名称：

  Highly Enantioselective Regiodivergent Allylic Alkylations of MBH Carbonates with Phthalides

  摘要：

  Phthalides were used for the first time in the allylic alkylation reactions with MBH carbonates for the creation of chiral 3,3-disubstituted phthalides. Highly enantioselective regiodivergent synthesis of gamma-selective or beta-selective allylic alkylation products was achieved by employing bifunctional chiral phosphines or multifunctional tertiary amine-thioureas as the catalyst, respectively. It was demonstrated that proper selection of catalysts and reaction conditions would differentiate an S(N)2'-S(N)2' pathway and an addition-elimination process, yielding different regioisomers of the allylic alkylation products in a highly enantiomerically pure form.

  DOI：

  10.1021/ja303115m
• 作为试剂：
  描述：

  3-氧代-1H-2-苯并呋喃-1-羧酸 在 4-二甲氨基吡啶 、 草酰氯 、 (2S,3R)-2-[[[[3,5-双(三氟甲基)苯基]氨基]硫代甲基]氨基]-N-(8Α,9S)-奎宁-9-基-3-[[(1,1-二甲基乙基)二苯基甲硅烷基]氧基]丁酰胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 40.0h， 生成 (S,Z)-tert-butyl 1-(2-cyano-3-(3-fluorophenyl)allyl)-3-oxo-1,3-dihydroisobenzofuran-1-carboxylate
  参考文献：
  名称：

  Highly Enantioselective Regiodivergent Allylic Alkylations of MBH Carbonates with Phthalides

  摘要：

  Phthalides were used for the first time in the allylic alkylation reactions with MBH carbonates for the creation of chiral 3,3-disubstituted phthalides. Highly enantioselective regiodivergent synthesis of gamma-selective or beta-selective allylic alkylation products was achieved by employing bifunctional chiral phosphines or multifunctional tertiary amine-thioureas as the catalyst, respectively. It was demonstrated that proper selection of catalysts and reaction conditions would differentiate an S(N)2'-S(N)2' pathway and an addition-elimination process, yielding different regioisomers of the allylic alkylation products in a highly enantiomerically pure form.

  DOI：

  10.1021/ja303115m