2-(Ethylsulfanyl)benzofuran | 172366-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-(Ethylsulfanyl)benzofuran
• 英文别名: 2-(ethylthio)benzo[b]furan；Benzofuran, 2-(ethylthio)-；2-ethylsulfanyl-1-benzofuran
• CAS: 172366-93-7
• 化学式: C₁₀H₁₀OS
• 分子量: 178.255
• InChiKey: HOJVIYBXEORQHM-UHFFFAOYSA-N

物化性质

• 沸点：
  273.0±13.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  chloroamine-T 、 2-(Ethylsulfanyl)benzofuran 以 乙醇 为溶剂， 反应 15.0h， 以46%的产率得到S-(benzo[b]furan-2-yl)-S-ethyl-N-(toluene-4-sulfonyl)sulfilimine
  参考文献：
  名称：

  一种基于乙烯基亚硫亚胺与二氯乙烯酮反应的γ-内酰胺的新合成方法。

  摘要：

  几种芳基，呋喃基和乙烯基取代的亚硫亚胺与二氯乙烯的反应在25℃进行，得到硫代烷基取代的γ-内酰胺，然后将其转化为多种含氮底物。[反应：看文字]

  DOI：

  10.1021/ol047453j
• 作为产物：
  描述：

  2,3-苯并呋喃 、 二乙基二硫醚 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 20.5h， 以64%的产率得到2-(Ethylsulfanyl)benzofuran
  参考文献：
  名称：

  一种基于乙烯基亚硫亚胺与二氯乙烯酮反应的γ-内酰胺的新合成方法。

  摘要：

  几种芳基，呋喃基和乙烯基取代的亚硫亚胺与二氯乙烯的反应在25℃进行，得到硫代烷基取代的γ-内酰胺，然后将其转化为多种含氮底物。[反应：看文字]

  DOI：

  10.1021/ol047453j

文献信息

• Dichloroketene-Induced Cyclizations of Vinyl Sulfilimines:  Application of the Method in the Synthesis of (±)-Desoxyeseroline
  作者：Albert Padwa、Shinji Nara、Qiu Wang

  DOI：10.1021/jo051550o

  日期：2005.10.1

  to yield thioalkyl-substituted γ-lactams. The overall process involves nucleophilic addition of the nitrogen atom of the sulfilimine onto the highly electrophilic dichloroketene to first generate a zwitterionic intermediate. A subsequent [3,3]-sigmatropic rearrangement is followed by intramolecular trapping of the Pummerer cation by the amido anion to furnish the observed γ-lactam product. Incorporation

  几种芳基，呋喃基和乙烯基取代的亚硫亚胺与二氯乙烯酮的反应在25°C下进行，得到硫代烷基取代的γ-内酰胺。整个过程包括将亚硫亚胺的氮原子亲核加成到高度亲电的二氯乙烯酮上，首先产生两性离子中间体。随后的[3,3]-σ重排，随后是酰胺阴离子在分子内捕获Pummerer阳离子，以提供所观察到的γ-内酰胺产物。当使用芳基取代的亚硫亚胺时，在磺酰基官能团的芳环上引入供体基团几乎没有影响，但是对与呋喃基取代的体系的反应效率显示出主要影响。电子给体基团的位置（即，磺酰基芳基上的OMe）提高了包含在sulf离子中间体中的酰胺基阴离子的亲核性，并促进了3，3-σ重排的速率。苯乙烯基取代的亚硫亚胺以立体有择的方式环化，并生成γ-内酰胺和异构的亚氨基-内酯体系的3：2混合物。高度官能化的γ-内酰胺易于转化为多种含氮底物。乙烯基亚砜亚胺环化方法应用于卡拉巴尔生物碱（±）-脱氧七氢呋喃的全合成。高度官能化的γ-内酰胺
• Free-Radical Addition of Heteroarenethiols and Heteroarylmethanethiols to Hexyne and Phenylacetylene. Chemical Behavior of the Transient .beta.-Sulfanylvinyl Radicals
  作者：Luisa Benati、Laura Capella、Pier Carlo Montevecchi、Piero Spagnolo

  DOI：10.1021/jo00129a039

  日期：1995.12

  The free-radical reaction of a number of heteroarenethiols (including 2-thiophene-, 2-benzo[b]furan-and 2-benzo[b]thiophenethiol) and heteroarylmethanethiols (including 2-furyl-, 2-thienyl-, and 3-thienylmethanethiol) with hex-1-yne and phenylacetylene has been investigated in benzene solution both at 100 degrees C in the presence of AIBN and at room temperature in the presence of BEt(3)/O-2. Under both of these conditions the above thiols generally furnished transient 2-sulfanylvinyl radicals through regioselective addition of corresponding sulfanyl radicals to the terminal alkyne carbon, but 2-benzo[b]furanthiol failed to react with either alkyne in the presence of BEt(3)/O-2 and unexpectedely gave 2-(ethylsulfanyl)benzo[b]furan to a significant extent. The produced 2-(2-heteroarylsulfanyl) vinyl radicals largely preferred to undergo intermolecular H-abstraction reaction rather than intramolecular 5-endo cyclization onto the heteroaryl moiety of the 2-sulfanyl substituent. The 2-[(2-thienylmethyl)sulfanyl]- and, especially, 2-[(2-furylmethyl)sulfanyl]vinyl radicals, besides H-abstraction, promptly underwent intramolecular B-exo cyclization to give spiro radicals that interestingly underwent beta-scission of their respective C-S and C-O bond resulting in ring cleavage of the original heteroaryl group. The 2-[(3-thienylmethyl)sulfanyl]vinyl radicals did not exhibit any similar B-exo cyclization, but did undergo a 6-endo cyclization to a very slight extent.
• A New Synthesis of γ-Lactams Based on the Reaction of Vinyl Sulfilimines with Dichloroketene
  作者：Qiu Wang、Shinji Nara、Albert Padwa

  DOI：10.1021/ol047453j

  日期：2005.3.1

  The reactions of several aryl-, furanyl-, and vinyl substituted sulfilimines with dichloroketene proceeded at 25 degrees C to yield thioalkyl substituted gamma-lactams which, in turn, were converted to a variety of nitrogen-containing substrates. [reaction: see text]

  几种芳基，呋喃基和乙烯基取代的亚硫亚胺与二氯乙烯的反应在25℃进行，得到硫代烷基取代的γ-内酰胺，然后将其转化为多种含氮底物。[反应：看文字]