N-tosylcyclopentanecarbamide | 121239-32-5

• 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: N-tosylcyclopentanecarbamide
• 英文别名: N-tosylcyclopentanecarboxamide；N-(4-methylphenyl)sulfonylcyclopentanecarboxamide
• CAS: 121239-32-5
• 化学式: C₁₃H₁₇NO₃S
• 分子量: 267.349
• InChiKey: VNFVBZKZRWJQNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-[1-Cyclopentyl-1-methoxy-meth-(Z)-ylidene]-4-methyl-benzenesulfonamide 在 air 作用下， 以18%的产率得到N-tosylcyclopentanecarbamide
  参考文献：
  名称：

  Semenov, V. P.; Ogloblin, K. A., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 11, p. 2154 - 2161

  摘要：

  DOI：

文献信息

• SULFONAMIDE-BASED ORGANOCATALYSTS AND METHOD FOR THEIR USE
  申请人：Carter Rich Garrett

  公开号：US20100184986A1

  公开（公告）日：2010-07-22

  Organocatalysts, particularly proline sulfonamide organocatalysts, having a first general formula as follows are disclosed. Embodiments of a method for using these organocatalysts also are disclosed. The method comprises providing a disclosed organocatalyst, and performing a reaction, often an enantioselective or diastereoselective reaction, using the organocatalyst. Solely by way of example, disclosed catalysts can be used to perform aldol reactions, conjugate additions, Michael additions, Robinson annulations, Mannich reactions, α-aminooxylations, α-hydroxyaminations, α-aminations and alkylation reactions. Certain of such reactions are intramolecular cyclizations used to form cyclic compounds, such as 5- or 6-membered rings, having one or more chiral centers. Disclosed organocatalysts generally are much more soluble in typical solvents used for organic synthesis than are known compounds. Moreover, the reaction yield is generally quite good with disclosed compounds, as is their enantioselective and diastereoselective effectiveness.

  披露了具有如下一般公式之一的有机催化剂，尤其是脯氨酸磺酰胺有机催化剂。还披露了使用这些有机催化剂的方法的实施例。该方法包括提供一种披露的有机催化剂，并使用该有机催化剂进行反应，通常是立体选择性的反应或对映选择性反应。仅作为示例，披露的催化剂可用于进行aldol反应、共轭加成、Michael加成、Robinson环化反应、Mannich反应、α-氨基氧化、α-羟基胺化、α-胺化和烷基化反应。其中一些反应是分子内环化反应，用于形成具有一个或多个手性中心的环状化合物，例如5或6元环。披露的有机催化剂通常比已知的化合物更容易溶于用于有机合成的典型溶剂中。此外，使用披露化合物的反应收率通常相当好，它们的对映选择性和非对映选择性效果也很好。
• Practical copper(i)-catalysed amidation of aldehydes
  作者：Joyce Wei Wei Chang、Thi My Uyen Ton、Stefani Tania、Paul C. Taylor、Philip Wai Hong Chan

  DOI：10.1039/b918588g

  日期：——

  The direct synthesis of amides by insertion into the C-H bond of aldehydes is shown to be a practical procedure through application of cheap, readily available catalysts generated in situ from copper(i) halides and pyridine.

  通过插入廉价的，容易获得的由卤化铜（i）和吡啶原位生成的催化剂，表明通过插入醛的CH键直接合成酰胺是一种实用的方法。
• Iron(II)-Catalyzed Amidation of Aldehydes with Iminoiodinanes at Room Temperature and under Microwave-Assisted Conditions
  作者：Thi My Uyen Ton、Ciputra Tejo、Stefani Tania、Joyce Wei Wei Chang、Philip Wai Hong Chan

  DOI：10.1021/jo200284a

  日期：2011.6.17

  A method for the amidation of aldehydes with PhI=NTs/PhI=NNs as the nitrogen source and an inexpensive iron(II) chloride + pyridine as the in situ formed precatalyst under mild conditions at room temperature or microwave assisted conditions is described. The reaction was operationally straightforward and accomplished in moderate to excellent product yields (20-99%) and with complete chemoselectivity with the new C-N bond forming only at the formylic C-H bond in substrates containing other reactive functional groups. By utilizing microwave irradiation, comparable product yields and short reaction times of 1 h could be accomplished. The mechanism is suggested to involve insertion of a putative iron-nitrene/imido group to the formylic C H bond of the substrate via a H-atom abstraction/radical rebound pathway mediated by the precatalyst [Fe(py)(4)Cl-2] generated in situ from reaction of FeCl2 with pyridine.
• Highly Efficient Ruthenium(II) Porphyrin Catalyzed Amidation of Aldehydes
  作者：Joyce Wei Wei Chang、Philip Wai Hong Chan

  DOI：10.1002/anie.200704695

  日期：2008.1.25
• CEMEHOB, V. P.;OGLOBLIN, K. A., ZH. ORGAN. XIMII, 24,(1988) N1, S. 2389-2397
  作者：CEMEHOB, V. P.、OGLOBLIN, K. A.

  DOI：——

  日期：——