(E)-5-(Phenylthio)pent-2-en-4-inal | 270918-58-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (E)-5-(Phenylthio)pent-2-en-4-inal
• 英文别名: 5-(phenylthio)pent-2-en-4-ynal；(E)-5-phenylsulfanylpent-2-en-4-ynal
• CAS: 270918-58-6
• 化学式: C₁₁H₈OS
• 分子量: 188.25
• InChiKey: VJHYJRHJOFWNTP-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-5-(Phenylthio)pent-2-en-4-inal 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 48.17h， 以77%的产率得到2-(bis(phenylthio)methyl)furan
  参考文献：
  名称：

  摘要：

  Contrary to expectations (Scheme 1), 5-(phenylthio)-(1a) as well as 5-(methylthio)pent-2-en-4-inal (1b) react with a slight excess of HCl to give 2-[bis( phenylthio)methyl] furan (17a, 77% yield) and 2-[bis(methylthio)methyl]furan (17b, 61% yield), respectively. Structures 17a and 17b are supported by the results of an X-ray crystal-structure analysis, by spectroscopic data in comparison to those of model compounds, and by synthesis of 17a. This surprising reaction is tentatively explained by a mechanism (Scheme 4), including a special pyran --> furan ring-contraction sequence, which is in agreement with a labelling experiment.

  DOI：

  10.1002/1522-2675(20000607)83:6<1191::aid-hlca1191>3.0.co;2-x
• 作为产物：
  描述：

  (E)-3-Iodoprop-2-enal 、 1-(phenylthio)-2-(trimethylstannyl)ethyne 在 四(三苯基膦)钯 Et₄(+)Cl(-) 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以58%的产率得到(E)-5-(Phenylthio)pent-2-en-4-inal
  参考文献：
  名称：

  摘要：

  含有乙氧基（EtO）、苯氧基（PhO）、苯硫基（PhS）和甲硫基（MeS）作为π供体的"推-拉"型炔烯化合物14a-d，通过催化条件下将炔亚胺锡化物10与3-碘丙-2-烯醛（Scheme 4）进行偶联反应而合成。

  DOI：

  10.1002/(sici)1522-2675(20000315)83:3<641::aid-hlca641>3.0.co;2-u

文献信息

• ——
  作者：Christian Bacilieri、Markus Neuenschwander

  DOI：10.1002/(sici)1522-2675(20000315)83:3<641::aid-hlca641>3.0.co;2-u

  日期：2000.3.15

  'Push-pull' enynes 14a-d with EtO, PhO, PhS, and MeS groups as pi-donors have been synthesized by catalyzed coupling of stannyl ynamines 10 with 3-iodoprop-2-enal (Scheme 4).

  含有乙氧基（EtO）、苯氧基（PhO）、苯硫基（PhS）和甲硫基（MeS）作为π供体的"推-拉"型炔烯化合物14a-d，通过催化条件下将炔亚胺锡化物10与3-碘丙-2-烯醛（Scheme 4）进行偶联反应而合成。
• ——
  作者：Christian Bacilieri、Markus Neuenschwander

  DOI：10.1002/1522-2675(20000607)83:6<1191::aid-hlca1191>3.0.co;2-x

  日期：2000.6.7

  Contrary to expectations (Scheme 1), 5-(phenylthio)-(1a) as well as 5-(methylthio)pent-2-en-4-inal (1b) react with a slight excess of HCl to give 2-[bis( phenylthio)methyl] furan (17a, 77% yield) and 2-[bis(methylthio)methyl]furan (17b, 61% yield), respectively. Structures 17a and 17b are supported by the results of an X-ray crystal-structure analysis, by spectroscopic data in comparison to those of model compounds, and by synthesis of 17a. This surprising reaction is tentatively explained by a mechanism (Scheme 4), including a special pyran --> furan ring-contraction sequence, which is in agreement with a labelling experiment.