(1S)-10-camphor-N-(pent-4-en-1-yl)sulfonamide | 127744-40-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S)-10-camphor-N-(pent-4-en-1-yl)sulfonamide
• 英文别名: 1-((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)-N-(pent-4-en-1-yl)methanesulfonamide；1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]-N-pent-4-enylmethanesulfonamide
• CAS: 127744-40-5
• 化学式: C₁₅H₂₅NO₃S
• 分子量: 299.434
• InChiKey: HHKAIAHPCGTCAE-IUODEOHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-10-camphor-N-(pent-4-en-1-yl)sulfonamide 在 sodium hypochlorite 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以89 %的产率得到(1S,4R)-1-(((2-(chloromethyl)pyrrolidin-1-yl)sulfonyl)methyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  Catalyst‐free Chloroamination Cyclization Cascade with Sodium Hypochlorite: from N‐(Pentenyl)sulfonylamides to 2‐(1‐Chloromethyl)pyrrolidines

  摘要：

  A mild and catalyst‐free protocol to obtain several 2‐chloromethylpyrrolidines by the use of a commercial solution of sodium hypochlorite is here reported, without the need for a light source. The choice of the solvent revealed to be crucial in the success of the reaction. Mechanistic studies, both experimental and computational, confirmed a radical mechanism, where the deprotonation step, followed by the oxidation of a N‐centered anion to the corresponding radical, allowed 2‐chloromethylpyrrolidines, by a very fast cyclization, to be obtained. Sodium hypochlorite plays the role of both the oxidant and the chlorine source.

  DOI：

  10.1002/ejoc.202400108
• 作为产物：
  描述：

  4-Penten-1-胺 、 右旋樟脑-10-磺酰氯 在 potassium hydroxide 作用下， 以 乙醚 为溶剂， 以25 %的产率得到(1S)-10-camphor-N-(pent-4-en-1-yl)sulfonamide
  参考文献：
  名称：

  Catalyst‐free Chloroamination Cyclization Cascade with Sodium Hypochlorite: from N‐(Pentenyl)sulfonylamides to 2‐(1‐Chloromethyl)pyrrolidines

  摘要：

  A mild and catalyst‐free protocol to obtain several 2‐chloromethylpyrrolidines by the use of a commercial solution of sodium hypochlorite is here reported, without the need for a light source. The choice of the solvent revealed to be crucial in the success of the reaction. Mechanistic studies, both experimental and computational, confirmed a radical mechanism, where the deprotonation step, followed by the oxidation of a N‐centered anion to the corresponding radical, allowed 2‐chloromethylpyrrolidines, by a very fast cyclization, to be obtained. Sodium hypochlorite plays the role of both the oxidant and the chlorine source.

  DOI：

  10.1002/ejoc.202400108

文献信息

• Oxidative Intramolecular Bromo-Amination of <i>N</i>-Alkenyl Sulfonamides via Umpolung of Alkali Metal Bromides
  作者：Katsuhiko Moriyama、Yuta Izumisawa、Hideo Togo

  DOI：10.1021/jo201113r

  日期：2011.9.2

  The oxidative intramolecular bromo-amination of various N-alkenyl sulfonamides and N-alkenoxyl sulfonamides via umpolung of alkali metal bromides occurred exo-selectively to generate cyclic bromoamides in high yields with good diastereoselectivities. This method provided the desired products without elaborating the stoichiometric amount of corresponding organic waste.
• Brønsted Acid-assisted Intramolecular Aminohydroxylation of <i>N</i>-Alkenylsulfonamides under Heavy Metal-free Conditions
  作者：Katsuhiko Moriyama、Yuta Izumisawa、Hideo Togo

  DOI：10.1021/jo301523a

  日期：2012.11.2

  The intramolecular aminohydroxylation of N-alkenylsulfonamides proceeded under heavy metal-free conditions to give substituted prolinol derivatives in high yields. Oxone activated by catalytic Bronsted acid worked well as an electrophilic oxidant for this reaction.