3-(p-tolylsulfinyl)-1H-pyrrole | 75421-89-5

• 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: 3-(p-tolylsulfinyl)-1H-pyrrole
• 英文别名: 3-(p-tolylsulfinyl)pyrrole；3-(p-Toluenesulfinyl)pyrrole；3-(4-methylphenyl)sulfinyl-1H-pyrrole
• CAS: 75421-89-5
• 化学式: C₁₁H₁₁NOS
• 分子量: 205.28
• InChiKey: XPFBVBDRJWLYGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(p-tolylsulfinyl)-1H-pyrrole 在 草酰氯 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 生成 2-chloro-3-toluenesulfonylpyrrole
  参考文献：
  名称：

  The total synthesis of ±-isoretronecanol from pyrrole

  摘要：

  DOI：

  10.1016/s0040-4039(00)98848-8
• 作为产物：
  描述：

  4-甲基苯基亚硫酰氯 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.08h， 生成 3-(p-tolylsulfinyl)-1H-pyrrole
  参考文献：
  名称：

  β-取代的吡咯通过正三异丙基甲硅烷基吡咯的亲电取代。

  摘要：

  N-三异丙基甲硅烷基吡咯在C-3处经受主要或排他的动力学亲电取代，并且由此获得的化合物在与四丁基氟化铵进行甲硅烷基化后，以良好的总收率得到3-取代的吡咯。

  DOI：

  10.1016/s0040-4039(00)86011-6

文献信息

• Regioselective and oxidant-free sulfinylation of indoles and pyrroles with sulfinamides
  作者：Yuan-Zhao Ji、Jin-Yu Zhang、Hui-Jing Li、Chunguang Han、Yi-Kun Yang、Yan-Chao Wu

  DOI：10.1039/c9ob00526a

  日期：——

  time-controlled highly selective C3- or C2-sulfinylation of pyrroles with sulfinamides is reported for the first time. The sulfinylation of indoles with sulfinamides using this protocol is oxidant-free and can be performed under obviously more feasible conditions (1.2 equiv. of indoles, 10 min) in comparison with the precedent procedure (3–20 equiv. of indoles, 16–18 h, ammonium persulfate as oxidant, hv). A

  首次报道了用亚磺酰胺意外地控制时间的高选择性吡咯的C3-或C2-亚磺酰基化。与先前的程序（3–20当量的吲哚，16–18）相比，使用该方案将亚吲哚的亚磺酰基进行亚磺酰胺化是无氧化剂的，并且可以在明显更可行的条件下进行（1.2当量的吲哚，10分钟）。 h，过硫酸铵作为氧化剂，hv）。可以容忍各种官能团，并且以中等至极好的收率获得了各种C2-硫代吲哚和C2 / 3-硫代吡咯。
• Efficient Synthesis of 3-(Arenesulfinyl)indoles in Water
  作者：Y. Liu、Z. Y. Zhang、Y. Z. Ji、H. J. Li、Y. C. Wu

  DOI：10.1134/s1070428021050109

  日期：2021.5

  sulfinylation of indoles with arylsulfinamides in water in the presence of trifluoroacetic acid as a promoter is described. The reaction occurs smoothly at room temperature under environmentally benign conditions without any catalyst, additive, ligand, or organic solvent. The developed sulfoxide synthetic protocol is attractive due to the use of water as the solvent and provides a novel and efficient route to

  摘要 描述了在三氟乙酸作为促进剂存在下，在水中用芳基亚磺酰胺对吲哚进行亚磺酰化的第一个例子。该反应在室温、环境友好的条件下顺利进行，无需任何催化剂、添加剂、配体或有机溶剂。由于使用水作为溶剂，开发的亚砜合成方案很有吸引力，并为广泛的功能化二芳基亚砜提供了一种新颖有效的途径。
• TMSOTf-Promoted Sulfinylation of Electron-Rich Aromatics with Sodium Arylsulfinates
  作者：Hui-Jing Li、Yan-Chao Wu、Yuan-Zhao Ji、Hao-Ran Yang、Zheng-Yan Zhang、Li-Jun Xie

  DOI：10.1055/s-0039-1691563

  日期：2020.3

  presence of TMSOTf is reported. Various electron-rich aromatics, including pyrroles, thiophenes, indoles, and electron-rich arenes, with sodium arylsulfinates are converted into the corresponding sulfoxides in moderate to excellent yields. This protocol possesses many advantages such as readily available and stable starting materials, broad substrate scopes, and transition-metal-free reaction conditions

  报道了一种新的无过渡金属路线，用于在 TMSOTf 存在下用芳基亚磺酸钠直接亚磺酰化富电子芳烃。各种富电子芳烃，包括吡咯、噻吩、吲哚和富电子芳烃，与芳基亚磺酸钠一起以中等至极好的收率转化为相应的亚砜。该协议具有许多优点，例如易于获得且稳定的起始材料、广泛的底物范围和无过渡金属的反应条件。
• The regiospecific Pummerer-like introduction of chlorine atoms into pyrrol-3-yl and indol-3-yl sulfoxides
  作者：Josefina Garcia、Claudio Ortiz、Robert Greenhouse

  DOI：10.1021/jo00246a048

  日期：1988.5
• N-(Triisopropylsilyl)pyrrole. A progenitor "par excellence" of 3-substituted pyrroles
  作者：Brian L. Bray、Peter H. Mathies、Reto Naef、Dennis R. Solas、Thomas T. Tidwell、Dean R. Artis、Joseph M. Muchowski

  DOI：10.1021/jo00313a019

  日期：1990.12

  A very effective strategy has been devised for the synthesis of 3-substituted pyrroles based on the use of the triisopropylsilyl (TIPS) moiety as a sterically demanding nitrogen substituent to obstruct the attack of electrophilic reagents at the alpha-positions. 1-(Triisopropylsilyl)pyrrole (1) undergoes highly preferential kinetic electrophilic substitution at the beta-position with a variety of electrophiles (Br+, I+, NO2+, RCO+, etc.) and fluoride ion induced desilylation of the products provides the corresponding 3-substituted pyrroles in good overall yields. Competitive trifluoroacetylation experiments demonstrate that substitution of TIPS-pyrrole at the alpha-positions is decelerated by a factor of > 10(4), vs pyrrole at the same sites, without affecting reactivity at the beta-positions. 1-(Triisopropylsilyl)-3-bromopyrrole (2) is readily converted into the 3-lithio compound 44 by bromine-lithium interchange with alkyllithium reagents. This previously unavailable, formal equivalent of 3-lithiopyrrole is itself an excellent source of a wide range of beta-substituted pyrroles, many of which would not be directly preparable from 1. TIPS-pyrrole can be 3,4-dihalogenated and these compounds undergo sequential halogen-metal interchange trapping reactions. This process is exemplified by an efficient, three-step synthesis of the antibiotic verrucarin E (63) from the dibromo compound 5.