2-(phenylthio)-3-(pyrrolidin-1-yl)naphthalene-1,4-dione | 500755-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(phenylthio)-3-(pyrrolidin-1-yl)naphthalene-1,4-dione
• 英文别名: 2-phenylsulfanyl-3-(pyrrolidin-1-yl)-1,4-naphthoquinone；1,4-Naphthalenedione, 2-(phenylthio)-3-(1-pyrrolidinyl)-；2-phenylsulfanyl-3-pyrrolidin-1-ylnaphthalene-1,4-dione
• CAS: 500755-47-5
• 化学式: C₂₀H₁₇NO₂S
• 分子量: 335.426
• InChiKey: JGUHCGZNGPYCHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(pyrrolidin-1-yl)naphthalene-1,4-dione 、 苯硫酚 在 碘苯二乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以81%的产率得到2-(phenylthio)-3-(pyrrolidin-1-yl)naphthalene-1,4-dione
  参考文献：
  名称：

  无金属、PhI(OAc)2 促进的氧化 C(sp2)-H 双官能化：硫胺化萘醌的合成

  摘要：

  在二乙酸苯基碘鎓 (III) (PIDA) 存在下，已开发出一种三组分硫胺化反应，导致形成硫胺化产物。这种催化方法代表了 1,4-萘醌的无金属硫胺化方法。观察到马来酰亚胺在这种无金属反应条件下也能顺利工作。本方法意味着通过一步过程进行氧化偶联反应，生成 CN 和 CS 键。各种芳香族和脂肪族硫醇和胺以 62-88% 的产率提供相应的硫代胺化化合物。根据少数对照实验预测了一个合理的反应途径。

  DOI：

  10.1002/adsc.202100796

文献信息

• 2-(Pyrrolidin-1-yl)-1,4-naphthoquinone and 2-phenylsulfanyl-3-(pyrrolidin-1-yl)-1,4-naphthoquinone
  作者：Daniel E. Lynch、Ian McClenaghan

  DOI：10.1107/s0108270102019194

  日期：2002.12.15

  The structure of 2-(pyrrolidin-1-yl)-1,4-naphthoquinone, C(14)H(12.9)5Cl(0.05)NO(2), (I), is actually a 0.95:0.05 mixture including 2-chloro-3-(pyrrolidin-1-yl)-1,4-naphthoquinone as a minor impurity, but (I) was resolved as a single molecule containing a Cl atom with 5% occupancy at the 3-position. Compound (I) was prepared from the fully chloro-substituted analogue in an attempt to produce the disubstituted pyrrolidinyl derivative. 2-Phenylsulfanyl-3-(pyrrolidin-1-yl)1,4-naphthoquinone, C20H17NO2S, (II), was also prepared from 2-chloro-3-(pyrrolidin-1-yl)-1,4-naphthoquinone, using a strong exocyclic nucleophile. The structure of (II) differs from previous structures of 2,3-dichloro-1,4-naphthoquinone and its derivatives in that the naphthoquinone ring is non-planar.
• Metal‐Free, PhI(OAc) ₂ ‐Promoted Oxidative C( <i>sp</i> ^<i>2</i> )−H Difunctionalization: Synthesis of Thioaminated Naphthoquinones
  作者：Satyajit Pal、Rana Chatterjee、Sougata Santra、Grigory V. Zyryanov、Adinath Majee

  DOI：10.1002/adsc.202100796

  日期：2021.12.7

  A three-component thioamination reaction has been developed in the presence of phenyliodonium(III) diacetate (PIDA) leading to the formation of a thioaminated products. This catalytic approach represents a method for the metal-free thioamination of 1,4-naphthoquinone. It was observed that maleimides also work smoothly under this metal-free reaction condition. This present method implies the oxidative

  在二乙酸苯基碘鎓 (III) (PIDA) 存在下，已开发出一种三组分硫胺化反应，导致形成硫胺化产物。这种催化方法代表了 1,4-萘醌的无金属硫胺化方法。观察到马来酰亚胺在这种无金属反应条件下也能顺利工作。本方法意味着通过一步过程进行氧化偶联反应，生成 CN 和 CS 键。各种芳香族和脂肪族硫醇和胺以 62-88% 的产率提供相应的硫代胺化化合物。根据少数对照实验预测了一个合理的反应途径。