N-(cyclohexylethynyl)-N-methylmethanesulfonamide | 1375101-95-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-(cyclohexylethynyl)-N-methylmethanesulfonamide
• 英文别名: N-(2-cyclohexylethynyl)-N-methylmethanesulfonamide
• CAS: 1375101-95-3
• 化学式: C₁₀H₁₇NO₂S
• 分子量: 215.316
• InChiKey: KSNXSKDGJNMRJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(cyclohexylethynyl)-N-methylmethanesulfonamide 、 间氯过氧苯甲酸 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以36%的产率得到
  参考文献：
  名称：

  β-Oxidation of Ynamides into N,O-Acetals by mCPBA: Application in Enantioselective Intermolecular Transacetalization

  摘要：

  Oxidation of ynamides by mCPBA led to beta-oxygenation and resulted in formation of carbonyl compounds with alpha-N,O-acetal functionality. These N,O-acetals are formed in high yields and can be stored indefinitely at room temperature. Yet, they can be activated by a chiral Bronsted acid and underwent an enantioselective transacetalization into a alpha-N,O-acetal. Subsequent diastereoselective transformations occurred with exceptional selectivity according to Felkin-Anh model.

  DOI：

  10.1021/acs.orglett.9b03411
• 作为产物：
  描述：

  N-甲基甲磺酰胺 、 2-溴乙炔基环己烷 在 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 以80%的产率得到N-(cyclohexylethynyl)-N-methylmethanesulfonamide
  参考文献：
  名称：

  Ru / PNNP催化的对映选择性菲西尼反应的双环[3.2.0]庚烷基酰胺：范围和在配体设计中的应用

  摘要：

  从[RuCl 2（PNNP）]中提取双氯化物[PNNP =（S，S）-N，N'-双[ o-（二苯基膦基）亚苄基]环己烷-1,2-二胺]给出了难以确定的双阳离子加合物[Ru（ OEt）2（PNNP）] 2+催化环状亚烷基β-酮酯与各种炔酰胺的[2 + 2]环加成反应，从而以高收率和对映选择性生产基于双环[3.2.0]庚烷的酰胺。讨论了这些产品的结构特征，并将选定的实例转换为高度模块化的二烯，亚磷酸酯-烯烃和二亚磷酸酯衍生物，将其作为Rh（I），Ir（I）和Pd（II）的双齿配体进行了测试。 不对称催化-联芳基-环加成-双环化合物-配体-磷-钌

  DOI：

  10.1055/s-0031-1289679

文献信息

• Iron(<scp>iii</scp>)-catalyzed tandem annulation of indolyl-substituted <i>p</i>-quinone methides with ynamides for the synthesis of cyclopenta[<i>b</i>]indoles
  作者：Ke-Yin Yu、Xiao-Min Ge、Yi-Jun Fan、Xiao-Tao Liu、Xue Yang、Yu-Han Yang、Xian-He Zhao、Xian-Tao An、Chun-An Fan

  DOI：10.1039/d2cc03252j

  日期：——

  two-carbon synthon has been explored for the first time in a novel iron(III)-catalyzed tandem annulation. This (2+2) annulation/retro-4π electrocyclization/imino-Nazarov cyclization cascade reaction is characterized by an unusual structural reconstruction of indolyl-substituted p-QMs, leading to an expeditious assembly of synthetically important functionalized cyclopenta[b]indoles.

  在新型铁( III )催化的串联环化反应中，首次探索了吲哚基取代的p -QMs作为新型双碳合成子的独特反应性。这种 (2+2) 环化/retro-4π 电环化/亚氨基-纳扎罗夫环化级联反应的特点是对吲哚基取代的p -QM 进行了不寻常的结构重建，从而导致合成重要的官能化环戊二烯[ b ]吲哚的快速组装。
• Bicyclo[3.2.0]heptane-Based Enamides by Ru/PNNP-Catalyzed Enantioselective Ficini Reactions: Scope and Application in Ligand Design
  作者：Antonio Mezzetti、Christoph Schotes、Raphael Bigler

  DOI：10.1055/s-0031-1289679

  日期：2012.2

  converted into highly modular diene, phosphite-alkene, and diphosphite derivatives, which were tested as bidentate ligands with Rh(I), Ir(I), and Pd(II). asymmetric catalysis - biaryls - cycloaddition - bicyclic compounds - ligands - phosphorus - ruthenium

  从[RuCl 2（PNNP）]中提取双氯化物[PNNP =（S，S）-N，N'-双[ o-（二苯基膦基）亚苄基]环己烷-1,2-二胺]给出了难以确定的双阳离子加合物[Ru（ OEt）2（PNNP）] 2+催化环状亚烷基β-酮酯与各种炔酰胺的[2 + 2]环加成反应，从而以高收率和对映选择性生产基于双环[3.2.0]庚烷的酰胺。讨论了这些产品的结构特征，并将选定的实例转换为高度模块化的二烯，亚磷酸酯-烯烃和二亚磷酸酯衍生物，将其作为Rh（I），Ir（I）和Pd（II）的双齿配体进行了测试。 不对称催化-联芳基-环加成-双环化合物-配体-磷-钌
• β-Oxidation of Ynamides into <i>N</i>,<i>O-</i>Acetals by <i>m</i>CPBA: Application in Enantioselective Intermolecular Transacetalization
  作者：Nguyen H. Nguyen、Quynh H. Nguyen、Soumen Biswas、Dilip V. Patil、Seunghoon Shin

  DOI：10.1021/acs.orglett.9b03411

  日期：2019.11.15

  Oxidation of ynamides by mCPBA led to beta-oxygenation and resulted in formation of carbonyl compounds with alpha-N,O-acetal functionality. These N,O-acetals are formed in high yields and can be stored indefinitely at room temperature. Yet, they can be activated by a chiral Bronsted acid and underwent an enantioselective transacetalization into a alpha-N,O-acetal. Subsequent diastereoselective transformations occurred with exceptional selectivity according to Felkin-Anh model.