(R)-N-[1-(3-methoxyphenyl)-2-methylene-3-oxobutyl]-4-methylbenzenesulfonamide | 1152292-52-8

• 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: (R)-N-[1-(3-methoxyphenyl)-2-methylene-3-oxobutyl]-4-methylbenzenesulfonamide
• 英文别名: 3-((3-methoxyphenyl)(tosylamino)methyl)but-3-en-2-one；N-[(1R)-1-(3-methoxyphenyl)-2-methylidene-3-oxobutyl]-4-methylbenzenesulfonamide
• CAS: 1152292-52-8
• 化学式: C₁₉H₂₁NO₄S
• 分子量: 359.446
• InChiKey: YQCHZETYCQBTFT-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-[(3-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 2.0h， 生成 (R)-N-[1-(3-methoxyphenyl)-2-methylene-3-oxobutyl]-4-methylbenzenesulfonamide
  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

• Planar chiral [2.2]paracyclophane-based phosphine-Brønsted acid catalysts bearing exceptionally high reactivity for aza-Morita–Baylis–Hillman reaction
  作者：Shinji Kitagaki、Yuu Ohta、Ryohei Takahashi、Mika Komizu、Chisato Mukai

  DOI：10.1016/j.tetlet.2012.11.021

  日期：2013.1

  planar chiral bifunctional phosphine compounds based on the [2.2]paracyclophane backbone with a pseudo-ortho substitution pattern have been synthesized and applied to the aza-Morita–Baylis–Hillman reaction. An enantiopure phosphine-phenol catalyst bearing an aryl group as a spacer connected to a phosphino group exhibited an exceptionally high reactivity (rt, 2–40 min) and good enantioselectivity (up to

  已经合成了几种新的基于[2.2]对环环烷骨架并具有假邻位取代模式的平面手性双官能膦化合物，并将其应用于氮杂-Morita-Baylis-Hillman反应。带有芳基作为间隔基连接至膦基的对映体纯正膦-苯酚催化剂具有极高的反应活性（室温，2–40分钟）和良好的对映选择性（高达85％ee）。
• 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.