N-(1-cyclohexyl-3-oxo-3-phenylpropyl)-4-methylbenzenesulfonamide | 1198790-83-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(1-cyclohexyl-3-oxo-3-phenylpropyl)-4-methylbenzenesulfonamide
• CAS: 1198790-83-8
• 化学式: C₂₂H₂₇NO₃S
• 分子量: 385.527
• InChiKey: YIAQXXFQVSXBCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲苯磺酰胺 在 1,2,2,6,6-五甲基哌啶 、 甲酸 、 三(五氟苯基)硼烷 、 sodium 4-methylbenzenesulfinate 作用下， 以 正己烷 、 水 、 甲苯 为溶剂， 反应 12.0h， 生成 N-(1-cyclohexyl-3-oxo-3-phenylpropyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  沮丧的路易斯酸/布朗斯台德碱催化剂促进的直接曼尼希型反应

  摘要：

  公开了直接曼尼希型反应，该反应通过多种羰基化合物和醛亚胺的反应提供α-和β-氨基酯。建议通过空间受阻的路易斯酸/布朗斯台德碱对促进转化，该碱对可协同操作：在催化剂配合物中生成烯醇盐，然后该烯醇盐与氢键活化的亚胺反应。反应物与催化剂之间的非共价相互作用为将来的催化剂设计提供了选择性和新的机会。

  DOI：

  10.1002/anie.201608583

文献信息

• Molecular sieve mediated decarboxylative Mannich and aldol reactions of β-ketoacids
  作者：Fangrui Zhong、Chunhui Jiang、Weijun Yao、Li-Wen Xu、Yixin Lu

  DOI：10.1016/j.tetlet.2013.06.030

  日期：2013.8

  A molecular sieve mediated decarboxylative Mannich reaction of β-ketoacids with sulfonyl imines is reported; this protocol leads to an efficient preparation of synthetically useful β-amino ketones. An analogous molecular sieve promoted decarboxylative aldol reaction between β-ketoacids and isatins is also described, which affords bioactive 3-substituted-3-hydroxy-oxindoles in excellent yields.

  报道了分子筛介导的β-酮酸与磺酰基亚胺的曼尼希脱羧反应。该方案可有效制备合成上有用的β-氨基酮。还描述了类似的分子筛促进的β-酮酸和靛红之间的脱羧醛醇缩合反应，其以优异的产率提供了生物活性的3-取代的-3-羟基-吲哚。
• Base-catalyzed three-component direct Mannich reaction of enolizable ketones with high syn-selectivities
  作者：Qunsheng Guo、John Cong-Gui Zhao、Hadi Arman

  DOI：10.1016/j.tetlet.2012.06.140

  日期：2012.9

  The three-component direct Mannich reaction between aldehydes, p-toluenesulfonamide, and enolizable ketones was achieved for the first time with organic bases as the catalysts. The corresponding N-tosylated β-aminoketones were obtained in high yields and good to excellent diastereoselectivities using TMG as the catalyst. Through reduction of the ketone group, the reaction product may be converted into

  醛，对甲苯磺酰胺和可烯醇化的酮之间的三组分直接曼尼希反应是首次使用有机碱作为催化剂实现的。使用TMG作为催化剂，以高收率和良好至优异的非对映选择性获得了相应的N-甲苯磺酸化的β-氨基酮。通过还原酮基，可以将反应产物以优异的非对映选择性转化为β-氨基。
• Simple and Efficient Access to <i>N</i>-Tosyl β-Amino Ketones and Their Conversion into 2,4-Disubstituted Azetidines
  作者：Biswanath Das、Penagaluri Balasubramanyam、Boyapati Veeranjaneyulu、Gandolla Chinna Reddy

  DOI：10.1021/jo901982n

  日期：2009.12.18

  Treatment of N-tosylaldimines with acetophenone at room temperature in the presence of Bf(3)center dot OEt2 as a catalyst furnished the corresponding N-tosyl beta-amino ketones in high yields (77-86%) within 6-9 h. Subsequent reduction and cyclization of these compounds afforded 2,4-disubstituted N-tosylazetidines, comprising a three-step, high-yielding synthesis starting from aldimines.
• Direct Mannich-Type Reactions Promoted by Frustrated Lewis Acid/Brønsted Base Catalysts
  作者：Jessica Z. Chan、Wenzhi Yao、Brian T. Hastings、Charles K. Lok、Masayuki Wasa

  DOI：10.1002/anie.201608583

  日期：2016.10.24

  Direct Mannich‐type reactions that afford both α‐ and β‐amino esters by the reaction of a broad range of carbonyl compounds and aldimines are disclosed. The transformation is promoted by a sterically frustrated Lewis acid/Brønsted base pair, which is proposed to operate cooperatively: Within the catalyst complex, an enolate is generated that then reacts with a hydrogen‐bond‐activated imine. Noncovalent

  公开了直接曼尼希型反应，该反应通过多种羰基化合物和醛亚胺的反应提供α-和β-氨基酯。建议通过空间受阻的路易斯酸/布朗斯台德碱对促进转化，该碱对可协同操作：在催化剂配合物中生成烯醇盐，然后该烯醇盐与氢键活化的亚胺反应。反应物与催化剂之间的非共价相互作用为将来的催化剂设计提供了选择性和新的机会。