3-((2-methoxyphenyl)(tosylamino)methyl)but-3-en-2-one | 1152292-51-7

• 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: 3-((2-methoxyphenyl)(tosylamino)methyl)but-3-en-2-one
• 英文别名: N-[(1R)-1-(2-methoxyphenyl)-2-methylidene-3-oxobutyl]-4-methylbenzenesulfonamide
• CAS: 1152292-51-7
• 化学式: C₁₉H₂₁NO₄S
• 分子量: 359.446
• InChiKey: NZCFCDFUQKCFIR-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丁烯酮 、 N-[(2-甲氧基苯基)亚甲基]-4-甲基苯磺酰胺 在 (S)-2-tert-butyl-6-((2'-(diphenylphosphino)-1,1'-binaphthyl-2-ylamino)methyl)-4-nitrophenol 、 苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 3-((2-methoxyphenyl)(tosylamino)methyl)but-3-en-2-one 、 3-((2-methoxyphenyl)(tosylamino)methyl)but-3-en-2-one
  参考文献：
  名称：

  三官能团有机催化剂促进的抗衡离子催化，在环境温度下可进行快速和对映选择性的aza-Morita-Baylis-Hillman反应†

  摘要：

  缺电子或富电子芳族N-甲苯磺酰基亚胺与甲基乙烯基酮 在室温下使用三官能有机催化剂以布朗斯台德碱作为质子化后的活性转换促进的不对称抗衡离子定向催化 苯甲酸。

  DOI：

  10.1039/b901781j

文献信息

• Trifunctional organocatalyst-promoted counterion catalysis for fast and enantioselective aza-Morita–Baylis–Hillman reactions at ambient temperature
  作者：Jean-Marc Garnier、Fei Liu

  DOI：10.1039/b901781j

  日期：——

  Fast and enantioselective aza-Morita–Baylis–Hillman reactions between electron-deficient or electron-rich aromatic N-tosyl imines and methyl vinyl ketone were achieved at ambient temperature using asymmetric counterion-directed catalysis promoted by trifunctional organocatalysts with a Brønsted base as the activity switch after protonation with benzoic acid.

  缺电子或富电子芳族N-甲苯磺酰基亚胺与甲基乙烯基酮 在室温下使用三官能有机催化剂以布朗斯台德碱作为质子化后的活性转换促进的不对称抗衡离子定向催化 苯甲酸。
• Enantioselective Trifunctional Organocatalysts for Rate- Enhanced Aza-Morita-Baylis-Hillman Reactions at Room Temperature
  作者：Jean-Marc Garnier、Christopher Anstiss、Fei Liu

  DOI：10.1002/adsc.200800679

  日期：2009.2

  Abstractmagnified imageA Brønsted acid‐activated trifunctional organocatalyst, based on the BINAP scaffold, was used for the first time to catalyze aza‐Morita‐Baylis–Hillman reactions between N‐tosylimines and methyl vinyl ketone with fast reaction rates and good enantioselectivity at room temperature. This trifunctional catalyst, containing a Lewis base, a Brønsted base, and a Brønsted acid, required acid activation to confer its enantioselectivity and rate improvement for both electron‐rich and electron‐deficient imine substrates. The role of the amino Lewis base of 1a was investigated and found to be the activity switch in response to an acid additive. The counterion of the acid additive was found to influence not only the excess ratio but also the sense of asymmetric induction.
• Cooperativity in the counterion catalysis of Morita/Baylis/Hillman reactions promoted by enantioselective trifunctional organocatalysts
  作者：Christopher Anstiss、Fei Liu

  DOI：10.1016/j.tet.2010.05.007

  日期：2010.7

  New trifunctional organocatalysts with a NHTs Brønsted acid were prepared and tested in their ability to promote the counterion catalysis of generic and aza-Morita/Baylis/Hillman reactions. The cooperativity between the counterion and the NHTs Brønsted acid of the trifunctional catalyst was required for good enantioselectivity and rate enhancement. Better enantioselectivity was observed for aza-MBH

  制备了具有NHTs布朗斯台德酸的新型三官能有机催化剂，并测试了它们促进普通反应和aza-Morita / Baylis / Hillman反应的抗衡离子催化能力。为了良好的对映选择性和速率提高，需要三官能催化剂的抗衡离子与NHTs布朗斯台德酸之间的协同作用。在较容易的条件下，在相对较低的催化剂负载量（2–5 mol％）下，氮杂-MBH反应观察到更好的对映选择性。