(S)-N-cyclohexyl-N-methyl-2-((4-methylphenyl)sulfonamido)propanamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N-cyclohexyl-N-methyl-2-((4-methylphenyl)sulfonamido)propanamide
• 英文别名: (2S)-N-cyclohexyl-N-methyl-2-[(4-methylphenyl)sulfonylamino]propanamide
• 化学式: C₁₇H₂₆N₂O₃S
• 分子量: 338.471
• InChiKey: DVZGVFIKODTFNY-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-N-cyclohexyl-N-methyl-2-((4-methylphenyl)sulfonamido)propanamide 在 碘 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以82%的产率得到(S)-1,3-dimethyl-4-tosyl-1,4-diazaspiro[4.5]decan-2-one
  参考文献：
  名称：

  Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N–H/C(sp³)–H Coupling

  摘要：

  An efficient method for the asymmetric synthesis of 4-imidazolidinones via an iodine-catalyzed intramolecular N-H/C(sp(3))-H activation of readily available and abundant feedstocks, amino acids, and amines is described. The reaction proceeded under visible light irradiation to afford a variety of 4-imidazolidinone derivatives under mild conditions in moderate to excellent yields. Secondary and tertiary C(sp(3))-H bonds were aminated, and various functional groups were tolerated.

  DOI：

  10.1021/acs.joc.9b01154
• 作为产物：
  描述：

  N-对甲苯磺酰-L-丙氨酸 在 氯化亚砜 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 (S)-N-cyclohexyl-N-methyl-2-((4-methylphenyl)sulfonamido)propanamide
  参考文献：
  名称：

  Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N–H/C(sp³)–H Coupling

  摘要：

  An efficient method for the asymmetric synthesis of 4-imidazolidinones via an iodine-catalyzed intramolecular N-H/C(sp(3))-H activation of readily available and abundant feedstocks, amino acids, and amines is described. The reaction proceeded under visible light irradiation to afford a variety of 4-imidazolidinone derivatives under mild conditions in moderate to excellent yields. Secondary and tertiary C(sp(3))-H bonds were aminated, and various functional groups were tolerated.

  DOI：

  10.1021/acs.joc.9b01154

文献信息

• Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N–H/C(sp³)–H Coupling
  作者：Kyalo Stephen Kanyiva、Marina Tane、Takanori Shibata

  DOI：10.1021/acs.joc.9b01154

  日期：2019.10.18

  An efficient method for the asymmetric synthesis of 4-imidazolidinones via an iodine-catalyzed intramolecular N-H/C(sp(3))-H activation of readily available and abundant feedstocks, amino acids, and amines is described. The reaction proceeded under visible light irradiation to afford a variety of 4-imidazolidinone derivatives under mild conditions in moderate to excellent yields. Secondary and tertiary C(sp(3))-H bonds were aminated, and various functional groups were tolerated.