3-methylpyrrolidine-2-thione | 127103-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫代内酰胺类
• 英文名称: 3-methylpyrrolidine-2-thione
• CAS: 127103-82-6
• 化学式: C₅H₉NS
• mdl: MFCD19217079
• 分子量: 115.199
• InChiKey: FDAQMCNWTHAERC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methylpyrrolidine-2-thione 在 三乙胺 作用下， 生成 8,8-dimethyl-2-phenyl-7,8-dihydro-6H-2,5a-diazo-as-indacene-1,3,5-trione
  参考文献：
  名称：

  Generation and cycloaddition reactions of transient alkyl-substituted anhydro-4-hydroxythiazolium hydroxides

  摘要：

  Transient alkyl-substituted anhydro-4-hydroxythiazolium hydroxides undergo efficient inter- and intramolecular cycloaddition to provide the corresponding 1,3-dipolar cycloadducts in high yield.

  DOI：

  10.1016/s0040-4039(00)61077-8
• 作为产物：
  描述：

  3-甲基-2-吡咯烷酮 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 以71 %的产率得到3-methylpyrrolidine-2-thione
  参考文献：
  名称：

  [EN] NOVEL IMIDAZOPYRIDINE AND PYRAZOLOPYRIDINE SULFONAMIDE DERIVATIVES
  [FR] NOUVEAUX DÉRIVÉS D'IMIDAZOPYRIDINE ET DE PYRAZOLOPYRIDINE SULFONAMIDE

  摘要：

  The invention relates to novel compounds having the general formula I wherein R1, R2, X1, X2,X3and W are as described herein, composition including the compounds and methods of using the compounds.

  公开号：

  WO2024017857A1

文献信息

• Intramolecular, Reductive Cyclization of ?-Ketoisothiocyanates Promoted by Using Samarium Diiodide
  作者：Min Seok Cho、In Sang Lee、Sung Ho Kang、Yong Hae Kim

  DOI：10.1002/chem.200400676

  日期：2005.2.18

  A novel samarium diiodide (SmI2) promoted intramolecular cyclization of beta-ketoisothiocyanate, derived from alpha,beta-unsaturated esters and ammonium thiocyanate led to alpha-hydroxythiolactams and/or thiolactams in high yields. Treatment of beta-ketoisothiocyanate with two equivalents of SmI2 gave a mixture of alpha-hydroxythiolactam and thiolactam. Four equivalents of SmI2 afforded only thiolactam

  新型的二碘化（（SmI2）促进了α-β-不饱和酯和硫氰酸铵衍生的β-酮异硫氰酸酯的分子内环化反应，从而高产率地产生了α-羟基硫代内酰胺和/或硫代内酰胺。用两当量的SmI 2处理β-酮异硫氰酸酯，得到α-羟基硫代内酰胺和硫代内酰胺的混合物。四当量的SmI2仅提供高收率的硫代内酰胺。分子内环化反应具有很高的立体选择性。提出了一种解释这种转变的机制。
• Generation of the Dihydro-5H-Thiazolo[3,2-a]pyridin-3-one Ring System by Proton Loss from Isothiomünchnones
  作者：Albert Padwa、Zhijia J. Zhang

  DOI：10.3987/com-93-s32

  日期：——

  Dihydro-5H-thiazolo[3,2-a]pyridin-3-ones are easily generated by proton loss from isothiomunchnones. The closely related tetrahydro-2H-pyrido[2,1-b]-[1,3]thiazin-4-one ring system was prepared by treating piperidine-2-thione with acryloyl chloride. These cyclic S,N-ketene acetals undergo smooth reaction with different electrophiles in the presence of Lewis acids.
• A short synthesis of (±)-alloyohimbane via a thioisomünchnone based intramolecular dipolar-cycloaddition reaction
  作者：Todd M. Heidelbaugh、Bing Liu、Albert Padwa

  DOI：10.1016/s0040-4039(98)00901-0

  日期：1998.7

  Thioisomunchnone dipoles were generated by the reaction of bromoalkenoyl chlorides with thioamides. The intramolecular dipolar-cycloaddition reaction was used for a short synthesis of the yohimbanoid alkaloid (+/-)-alloyohimbane. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A One-Pot Bicycloannulation Method for the Synthesis of Tetrahydroisoquinoline Systems
  作者：Albert Padwa、L. Scott Beall、Todd M. Heidelbaugh、Bing Liu、Scott M. Sheehan

  DOI：10.1021/jo991742h

  日期：2000.5.1

  A highly effective method for the synthesis of the core indolo[2,3-a]quinolizidine skeleton found in yohimbine is described. The reaction of N-monosubstituted thioamides with bromoalkenoyl chlorides furnishes thioisomunchnones as transient 1,3-dipoles that undergo ready intramolecular cycloaddition across the tethered pi-bond to give thio-bicycloannulated products in a one-pot operation. The stereochemical outcome of the intramolecular reaction is the consequence of an endo cycloaddition of the neighboring-bond across the transient thioisomunchnone dipole. A major limitation of the method is that when a hydrogen is present in the alpha-position of the thioamide the initially formed thio-N-acyliminium ion undergoes proton loss to produce a S ,N-ketene acetal at a faster rate than dipole formation. Treatment of tetrahydro-beta-carboline-1-thione with 2-bromooct-7-enoyl chloride followed by reductive removal of sulfur from the cycloadduct resulted in the formation of (+/-)-alloyahimbanone. Attempts to cycloadd the thioisomunchnone dipole across several nucleophilic-bonds failed, and instead, products derived from cyclization of the pi-bond onto the initially formed thio-N-acyliminium ion were formed. The resulting N,S-ketals were further converted into several tetrahydroisoquinoline alkaloids in good yield.
• Padwa Albert, Zhang Zhijia J., Heterocycles, 37 (1994) N 1, S 441-459
  作者：Padwa Albert, Zhang Zhijia J.

  DOI：——

  日期：——