but-2-yn-1-yldimethylsulfonium bromide | 23451-60-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: but-2-yn-1-yldimethylsulfonium bromide
• 英文别名: Dimethyl-(butin-(2)-yl)-sulfonium-bromid；but-2-ynyl-dimethyl-sulfonium; bromide；But-2-ynyl(dimethyl)sulfanium;bromide；but-2-ynyl(dimethyl)sulfanium;bromide
• CAS: 23451-60-7
• 化学式: Br*C₆H₁₁S
• 分子量: 195.123
• InChiKey: DMGFTGUFOSVVKT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.11
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  but-2-yn-1-yldimethylsulfonium bromide 在 manganese(IV) oxide 、 sodium hydride 作用下， 生成 4-Methyl-5-methylsulfanyl-1-phenyl-penta-2,3-dien-1-one
  参考文献：
  名称：

  Terada,A.; Kishida,Y., Chemical and pharmaceutical bulletin, 1970, vol. 18, p. 497 - 504

  摘要：

  DOI：
• 作为产物：
  描述：

  二甲基硫 、 1-溴-2-丁炔 以 丙酮 为溶剂， 生成 but-2-yn-1-yldimethylsulfonium bromide
  参考文献：
  名称：

  用于合成四氢喹喔啉的二胺和 prop-2-ynyl 硫盐的正式 [4 + 2] 环化

  摘要：

  开发了二胺和 prop-2-ynyl 硫盐的正式 [4 + 2] 环化反应。该策略能够以优异的收率有效地获得四氢喹喔啉。

  DOI：

  10.1039/d2ob01590k

文献信息

• Combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement to construct homoallyl sulfur-containing pyrazolones
  作者：Shou-Jie Shen、Xiao-Li Du、Xiao-Li Xu、Yue-Hua Wu、Ming-gang Zhao、Jin-Yan Liang

  DOI：10.1039/c9ra07610g

  日期：——

  3]-sigmatropic rearrangement reaction of α-alkylidene pyrazolinones and propargyl sulfonium salts has been reported to construct homoallyl sulfur-containing pyrazolones with moderate to excellent yields. α-Alkylidene pyrazolinones function as N-nucleophilic agents distinguished from the reported C-addition reactions. Propargyl sulfonium salts were first involved in the [2,3]-sigmatropic rearrangement protocol

  据报道，第一个顺序组合的无机碱促进了α-亚烷基吡唑啉酮和炔丙基锍盐的N-加成/[2,3]-σ重排反应，以中等至优异的产率构建了高烯丙基含硫吡唑啉酮。 α-亚烷基吡唑啉酮作为 N-亲核试剂，与报道的 C-加成反应不同。炔丙基锍盐首先参与与成熟的成环反应不同的[2,3]-σ重排方案。优异的区域选择性、广泛的底物范围、克级合成和便捷的转化体现了该级联过程的合成优势。
• 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。
• Divergent Domino Reactions of Prop-2-ynylsulfonium Salts: Access to Sulfur-Containing Benzo-Fused Dioxabicyclo[3.3.1]nonanes and Dihydrofuro[2,3-<i>c</i>]chromenes
  作者：Yiming Zhou、Yu Chen、You Huang

  DOI：10.1021/acs.orglett.0c02025

  日期：2020.8.7

  domino annulation reactions between 2-hydroxy-2-methylchromene derivatives and prop-2-ynylsulfonium salts have been developed. Specifically, a sequential [4 + 2] and [4 + 2] annulation reaction occurred in 1,2-dichloroethane affording sulfur-containing benzo-fused dioxabicyclo[3.3.1]nonanes. In contrast, by changing the solvent to toluene, the reaction course switched to a [4 + 2] and [4 + 1] annulation

  已经开发了2-羟基-2-甲基苯甲基衍生物和丙-2-炔基ulf盐之间的溶剂控制的发散性多米诺环化反应。具体地，在[1，2-二氯乙烷]中发生顺序的[4 + 2]和[4 + 2]环化反应，得到含硫的苯并稠合的二氧杂双环[3.3.1]壬烷。相反，通过将溶剂改变为甲苯，反应过程切换为[4 + 2]和[4 +1]环化反应，得到二氢呋喃[2,3- c ]二甲基苯。值得注意的是，丙-2-炔基salt盐首次以其γ-碳原子参与转化。
• A Formal [3+2] Annulation of <i>β</i> ‐Oxoamides and 3‐Alkyl‐ or 3‐Aryl‐Substituted Prop‐2‐Ynyl Sulfonium Salts: Substrate‐Controlled Chemoselective Synthesis of Substituted <i>γ</i> ‐Lactams and Furans
  作者：Bicheng Deng、Chitturi Bhujanga Rao、Rui Zhang、Jiacheng Li、Yongjiu Liang、Yanning Zhao、Ming Gao、Dewen Dong

  DOI：10.1002/adsc.201900693

  日期：2019.10.8

  A substrate‐controlled synthesis of substituted γ‐lactams and furans has been developed via a formal [3+2] annulation of β‐oxoamides and 3‐alkyl/arylprop‐2‐ynyl sulfonium salts in the presence of cesium carbonate in a chemoselective manner. This novel protocol features easily available starting materials, mild reaction conditions, simple execution, and good to excellent yields of products.

  取代的甲基片控制的合成γ β-内酰胺类和呋喃已经开发通过正式[3 + 2]环β在碳酸铯的存在下和-oxoamides 3-烷基/ arylprop -2-炔基锍盐在化学选择性的方式。这种新颖的方案具有容易获得的起始原料，温和的反应条件，简单的实施以及良好至极好的产品收率的特点。
• Synthesis of methylene cyclopropane-fused chromenes and dihydroquinolines by sequential [4 + 2]- and [1 + 2]-annulation
  作者：Tianyu Lu、Xuange Zhang、Zhiwei Miao

  DOI：10.1039/d0ob00389a

  日期：——

  A base promoted sequential [4 + 2]- and [1 + 2]-annulation of 2-hydroxychalcones or 2-tosylaminochalcones with prop-2-ynylsulfonium salts has been developed to give the corresponding methylene cyclopropane fused dihydroquinolines or chromenes in moderate to good yields. This transformation has advantage of wide substrate scope and functional group tolerance as well as excellent regioselectivity. Prop-2-ynylsulfonium

  已开发出具有碱促进的2-羟基查尔酮或2-甲苯磺酰基al与丙-2-炔基salts盐依次[4 + 2]-和[1 + 2]环化的方法，可得到中等至良好的相应亚甲基环丙烷稠合的二氢喹啉或色烯。产量。这种转变的优点是底物范围广，官能团耐受性好以及区域选择性好。丙-2-炔基salts盐在串联过程中同时充当C2和C1合成子。