3,4-Dihydro-1-methyl-2(methylthio)-5H-pyrrolium iodide | 25355-40-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3,4-Dihydro-1-methyl-2(methylthio)-5H-pyrrolium iodide
• 英文别名: 1-methyl-5-methylsulfanyl-3,4-dihydro-2H-pyrrol-1-ium;iodide
• CAS: 25355-40-2
• 化学式: C₆H₁₂NS*I
• 分子量: 257.138
• InChiKey: AHFJUVHYZIDXRK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.44
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  28.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-Dihydro-1-methyl-2(methylthio)-5H-pyrrolium iodide 在 potassium tert-butylate 作用下， 生成 1-甲基-5-(甲硫基)-2,3-二氢-1H-吡咯
  参考文献：
  名称：

  Coupling-Isomerization−N,S-Ketene Acetal-Addition SequencesA Three-Component Approach to Highly Fluorescent Pyrrolo[2,3-b]pyridines, [1,8]Naphthyridines, and Pyrido[2,3-b]azepines

  摘要：

  Annelated 2-amino pyridines such as pyrrolo[2,3-b]pyridines, [1,8]naphthyridines, and pyrido[2,3-b]azepines can be synthesized in moderate to good yields in a consecutive one-pot three-component process by a coupling-isomerization-enamine-addition-cyclocondensation sequence of an electron-poor (hetero)aryl halide, a terminal propargyl N-tosylamine, and an N,S-ketene acetal. After the coupling-isomerization sequence, a Diels-Alder reaction with inverse electron demand of the intermediate enimine and the N,S-ketene acetal and subsequent aromatization furnish annelated 2-amino pyridines 4 that were unambiguously characterized by numerous X-ray structure analyses. These heterocycles are highly fluorescent and partially pH sensitive, and their electronic structure was studied with spectroscopic and computational methods.

  DOI：

  10.1021/jo0602726
• 作为产物：
  描述：

  N-甲基吡咯烷酮 在 diphosphorus pentasulfide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3,4-Dihydro-1-methyl-2(methylthio)-5H-pyrrolium iodide
  参考文献：
  名称：

  乙烯基磺酰胺（β-磺酰基烯胺）的制备和还原转化，及其在吲哚并咪唑合成中的应用。

  摘要：

  1-烷基吡咯烷-2-硫酮的甲硫盐与[（4-甲基苯基）磺酰基]乙酸乙酯或1-[（4-甲基苯基）磺酰基]丙-2-酮的缩合得到几种2-[[（（4-甲基苯基）]磺酰基]亚甲基]吡咯烷类化合物收率好。这些β-磺酰基烯胺具有足够的亲核性，可以与内部亲电试剂进行环化反应，从而得到砜取代的吲哚利嗪，这是潜在的有用的生物碱合成骨架。通过催化氢化或用硼氢化钠处理可选择性地立体还原乙烯基磺酰胺中的碳-碳双键，生成β-磺胺。β-酰基-β-磺酰基烯胺中的砜基可通过在THF-甲醇中用汞齐钠进行氢解反应而除去，得到烯胺酮。

  DOI：

  10.1039/b413379j

文献信息

• Synthesis of 5-Amino-4-(2-azacycloalkylidene)-2-phenyl-2,4-dihydro-3<i>H</i>-pyrazol-3-ones
  作者：Konstantin Nazarenko、Sergey Bova、Vitaliy Polovinko、Andrey Tolmachev

  DOI：10.1055/s-0028-1083183

  日期：——

  The reaction 5-amino-2-phenyl-3,4-dihydro-3H-pyrazol-3-one with activated lactams (lactim ethers, lactam acetals, and methylthioalkylidene iminium salts) was investigated. It occurs on the active methylene group of 5-amino-2-phenyl-3,4-dihydro-3H-pyrazol-3-one to furnish cyclic enamines, 5-amino-4-(2-azacycloalkylidene)-2-phenyl-2,4-dihydro-3H-pyrazol-3-ones and 5-amino-4-(1-methyl-2-azacycloalkylidene)-2-phenyl-2,4-dihydro-3H-pyrazol-3-ones.

  研究了5-氨基-2-苯基-3,4-二氢-3H-吡唑-3-酮与活化的内酰胺（内酰胺醚、内酰胺缩醛和甲硫基烯亚胺盐）的反应。反应发生在5-氨基-2-苯基-3,4-二氢-3H-吡唑-3-酮的活性亚甲基上，生成环状烯胺、5-氨基-4-(2-氮杂环烷亚基)-2-苯基-2,4-二氢-3H-吡唑-3-酮和5-氨基-4-(1-甲基-2-氮杂环烷亚基)-2-苯基-2,4-二氢-3H-吡唑-3-酮。
• Inverse-electron-demand diels-alder reactions of condensed pyridazines, part 1. Synthesis of phthalazine derivatives from pyridazino[4,5-d]pyridazines.
  作者：Norbert Haider

  DOI：10.1016/s0040-4020(01)86436-x

  日期：1991.1

  The 1,4-diarylpyridazino[4,5-d]pyridazine derivatives 1a,b were found to undergo [4+2] cycloaddition reactions with a variety of electron-rich dienophiles like enamines and ketene acetals to afford phthalazine derivatives in good to high yields.

  发现1,4-二芳基哒嗪并[4,5- d ]哒嗪衍生物1a，b与各种富含电子的亲二烯体，如烯胺和乙烯酮乙缩醛进行[4 + 2]环加成反应，得到高至高价的邻苯二嗪衍生物。产量。
• Domino Reactions of 4,5-Dicyanopyridazine with Dihydroheterocycles:  Synthetic and Mechanistic Features
  作者：Donatella Giomi、Marco Cecchi

  DOI：10.1021/jo026761x

  日期：2003.4.1

  4-dihydro-2H-pyran (9) to give the tetracyclic skeletons 5-8 and the phthalonitrile 12 through the intermediates 4 and 10, respectively. A more complex mechanism was ascertained for the reaction of 1 with the pyrroline 14 which, under suitable conditions, afforded the bicyclic derivative 19 as the predominant product; selective elaborations of this species into the 5,6-dicyanoindoles 22 and 23 are reported.

  发现标题哒嗪1与2,3-二氢呋喃（2）和3,4-二氢-2H-吡喃（9）反应，通过中间体4和10得到四环骨架5-8和邻苯二甲腈12，分别。对于1与吡咯啉14的反应，确定了更复杂的机理，其在合适的条件下提供了作为主要产物的双环衍生物19。据报道该物种选择性地进入5，6-二氰基吲哚22和23。
• Methods for converting N-alkyl lactams to vinylogous urethanes and vinylogous amides via(methylthio)alkylideniminium salts
  作者：Mary M. Gugelchuk、David J. Hart、Yeun-Min Tsai

  DOI：10.1021/jo00331a018

  日期：1981.8
• Singh, Paramjut; Batra, Manohar S.; Singh, Harjit, Synthetic Communications, 1984, vol. 14, # 6, p. 533 - 536
  作者：Singh, Paramjut、Batra, Manohar S.、Singh, Harjit

  DOI：——

  日期：——