1-prop-2-ynyl-tetrahydro-thiophenium; bromide | 35851-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: 1-prop-2-ynyl-tetrahydro-thiophenium; bromide
• 英文别名: 1-(Prop-2-yn-1-yl)thiolan-1-ium bromide；1-prop-2-ynylthiolan-1-ium;bromide
• CAS: 35851-39-9
• 化学式: Br*C₇H₁₁S
• 分子量: 207.134
• InChiKey: WTOCDWZZOWYONU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.96
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  、 1-prop-2-ynyl-tetrahydro-thiophenium; bromide 在 caesium carbonate 作用下， 以 氯仿 为溶剂， 反应 18.0h， 以78%的产率得到(4-fluorophenyl){(1R,5S,6R)-2-methylene-3-tosyl-3-azabicyclo[3.1.0]hexan-6-yl}methanone
  参考文献：
  名称：

  丙二炔基Salt盐和甲苯磺酰基氨基甲基烯酮的正序[1 + 2]-和[2 + 3]-环加成反应获得的亚甲基双氮杂[3.1.0]己烷一锅法合成环丙烷

  摘要：

  开发了正式的序贯[1 + 2]-和[2 + 3]-丙-2-炔基salts盐和甲苯磺酰基氨基甲基烯酮的环，构造了一系列亚甲基氮杂双环[3.1.0]己烷衍生物。通过烯胺中间体的水合建立一锅法，得到取代的环丙烷。丙-2-炔基salts盐在这两个过程中均充当C 2和C 1合成子。

  DOI：

  10.1002/adsc.201700959

文献信息

• Regioselective N-Addition/Substitution Reaction of α-Alkylidene Pyrazolinones with Propargyl Sulfonium Salts to Construct Allylthio-Containing Pyrazolones
  作者：Shou-Jie Shen、Xiao-Li Du、Xiao-Li Xu、Ming-Gang Zhao、Jin-Yan Liang

  DOI：10.1021/acs.joc.9b02029

  日期：2019.10.4

  The regioselective N-addition/substitution reaction between α-alkylidene pyrazolinones and propargyl sulfonium salts has been developed to construct functionalized allylthio-containing pyrazolones with moderate to excellent yields. α-Alkylidene pyrazolinones act as N-nucleophilic agents which are distinguished from reported C-nucleophilic reactions. Excellent regioselectivity, readily available starting

  已经开发了α-亚烷基吡唑啉酮类与炔丙基salts盐之间的区域选择性N-加成/取代反应，以中等至优异的产率构建官能化的含烯丙基硫基的吡唑啉酮。α-亚烷基吡唑啉酮类作为N-亲核试剂，与已报道的C-亲核反应不同。出色的区域选择性，易于获得的起始原料，广泛的底物范围，克级合成以及简单的操作，说明了这种新反应途径的合成优势。
• The reaction of prop-2-ynylsulfonium salts and sulfonyl-protected β-amino ketones to epoxide-fused 2-methylenepyrrolidines and S-containing pyrroles
  作者：Tingting Jia、Gongruixue Zeng、Chong Zhang、Linghui Zeng、Wenya Zheng、Siyao Li、Keyi Wu、Jiaan Shao、Jiankang Zhang、Huajian Zhu

  DOI：10.1039/d0cc07745c

  日期：——

  A novel divergent domino annulation reaction of prop-2-ynylsulfonium salts with sulfonyl-protected β-amino ketones has been developed, affording various epoxide-fused 2-methylenepyrrolidines and S-containing pyrroles in moderate to excellent yields. Prop-2-ynylsulfonium salts act as C2 synthons in the reactions providing a promising epoxide-fused skeleton in a single operation with readily accessible

  已经开发了丙-2-炔基salts盐与磺酰基保护的β-氨基酮的新型发散性多米诺环化反应，以中等到极好的收率提供了各种环氧化物稠合的2-亚甲基吡咯烷和含S的吡咯。丙-2-炔基salts盐在反应中充当C 2合成子，可通过易于操作的起始原料在单次操作中提供有希望的环氧融合骨架。
• Elimination–addition. Part XXI. Addition–dealkylation reactions of acetylenic sulphonium salts with oxygen, sulphur, and nitrogen nucleophiles
  作者：J. W. Batty、P. D. Howes、C. J. M. Stirling

  DOI：10.1039/p19730000059

  日期：——

  Reactions of nucleophiles with dimethylprop-2-ynylsulphonium and S-prop-2-ynyltetrahydrothiophenium bromides have been investigated. These salts readily isomerise to the allenic isomers ([graphic omitted]·C:C:C), which are susceptible to nucleophilic addition. The initially formed adducts, according to their structure, undergo several types of subsequent reaction. Most commonly, isomerisation of the

  已经研究了亲核试剂与二甲基丙-2-炔基and和S-丙-2-炔基四氢噻吩溴化物的反应。这些盐易于异构化为易于亲核加成的烯丙二烯异构体（[省略图示]·C：C：C）。最初形成的加合物，根据其结构，会经历几种类型的后续反应。最通常地，将初始非共轭加合物异构化成共轭异构体，或者随后添加第二亲核试剂，或者亲核试剂通过攻击邻近硫的碳使ates基脱烷基。在环状sulph盐的情况下，脱烷基作用导致环裂解并形成开链硫化物。
• [3 + 2]-Annulation of Prop-2-ynylsulfonium Salts: Access to Hydroindol-5-ones Containing a Methylthio Group
  作者：Penghao Jia、Qinglong Zhang、Hongxing Jin、You Huang

  DOI：10.1021/acs.orglett.6b03667

  日期：2017.1.20

  An unprecedented [3 + 2]-annulation of prop-2-ynylsulfonium salts and p-quinamines was developed, affording a series of hydroindol-5-ones with a methylthio group in moderate to good yields under mild conditions. In this reaction, the prop-2-ynylsulfonium salt acts as a novel C2 synthon and sulfide does not serve as a leaving group, which provides facile access to organosulfur compouds.

  开发了空前的[3 + 2]环丙基丙炔基salts盐和对苯二胺，在温和条件下以中等到良好的收率得到了一系列带有甲硫基的氢化吲哚-5-酮。在该反应中，丙-2-炔基salt盐起新颖的C 2合成子的作用，而硫化物不充当离去基团，这提供了容易获得有机硫化合物的途径。
• Sequential [1 + 4]- and [2 + 3]-Annulation of Prop-2-ynylsulfonium Salts: Access to Hexahydropyrrolo[3,2-<i>b</i>]indoles
  作者：Penghao Jia、Qinglong Zhang、Qima Ou、You Huang

  DOI：10.1021/acs.orglett.7b02298

  日期：2017.9.1

  A powerful sequential [1 + 4]- and [2 + 3]-annulation has been developed using prop-2-ynylsulfonium salts and sulfonyl-protected o-amino aromatic aldimines, affording a series of hexahydropyrrolo[3,2-b]indoles in high yields. Prop-2-ynylsulfonium salts act as C2 synthons in the reaction, and fused rings containing two five-membered azaheterocycles can be constructed in a single operation with readily

  使用丙-2-炔基salts盐和磺酰基保护的邻氨基芳族亚胺开发了有力的顺序[1 + 4]-和[2 + 3]环化反应，提供了一系列的六氢吡咯并[3,2- b ]吲哚高产。丙-2-炔基salts盐在反应中充当C 2合成子，并且可以在一次操作中使用易于获得的起始原料构建包含两个五元氮杂杂环的稠合环。