2-chloro-3-(2’-hydroxyethylsulfanyl)prop-1-en | 5310-35-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-chloro-3-(2’-hydroxyethylsulfanyl)prop-1-en
• 英文别名: 2-(2-chloroallylthio)ethanol；2-(2-Chloroprop-2-enylsulfanyl)ethanol
• CAS: 5310-35-0
• 化学式: C₅H₉ClOS
• 分子量: 152.645
• InChiKey: CZYDBTPROYFCRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-3-(2’-hydroxyethylsulfanyl)prop-1-en 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以13.1%的产率得到5,6-dihydro-2-methyl-1,4-oxathiine
  参考文献：
  名称：

  Synthesis and carbon-13 nuclear magnetic resonance spectroscopy of 5,6-dihydro-2-methyl-1,4-oxathiin,trans-tetrahydro-1,4-benzoxathiin, 1,4-tetrahydro-[9,10]benzoxathiin, the 4-oxides, 4,4-dioxides and related acyclic compounds

  摘要：

  AbstractThe results of a 13C NMR spectral investigation involving 5,6‐dihydro‐1,4‐oxathiins, 1,4‐tetrahydro[9,10]benzoxathiin, trans‐tetrahydro‐1,4‐benzoxathiin, and the corresponding sulfoxides and sulfones are reported. An interpretation involving a dipolar structure with (2p→2p)π conjugation as opposed to (2p→3d)π interactions with the vinyloxy sulfides seems consistent with trends in the 13C NMR shifts. For the sulfoxides and sulfones, the substitutent‐induced chemical shift (SCS) effects at the β vinylic carbons (βSO and βSO2 effects) are considerably less than those at sp3 carbons. The γSO and γSO2 values at the sp2γ carbons indicate deshielding, in contrast to the shielding at the sp3 carbons.

  DOI：

  10.1002/mrc.1270160404
• 作为产物：
  描述：

  S-(2-chloroprop-2-en-1-yl)isothiuronium chloride 、 2-氯乙醇 在 一水合肼 、 potassium hydroxide 作用下， 反应 10.5h， 以87%的产率得到2-chloro-3-(2’-hydroxyethylsulfanyl)prop-1-en
  参考文献：
  名称：

  Features of the synthesis of unsaturated sulfides proceeding from (2-chloroprop-2-en-1-yl)isothiouronium chloride

  摘要：

  Procedure of synthesis of sulfides containing a chloropropenyl fragment sensitive to bases was modified. The change in the sequence of reagents addition ensuring a contact of isothiouronium salt with a minimal base quantity and the application of a mixture hydrazine hydrate-alkali allowed the preparation of target sulfides under mild conditions in up to 93% yields.

  DOI：

  10.1134/s1070428015020037

文献信息

• Features of the synthesis of unsaturated sulfides proceeding from (2-chloroprop-2-en-1-yl)isothiouronium chloride
  作者：E. P. Levanova、V. S. Vakhrina、V. A. Grabel’nykh、I. B. Rozentsveig、N. V. Russavskaya、A. I. Albanov、E. R. Sanzheeva、N. A. Korchevin

  DOI：10.1134/s1070428015020037

  日期：2015.2

  Procedure of synthesis of sulfides containing a chloropropenyl fragment sensitive to bases was modified. The change in the sequence of reagents addition ensuring a contact of isothiouronium salt with a minimal base quantity and the application of a mixture hydrazine hydrate-alkali allowed the preparation of target sulfides under mild conditions in up to 93% yields.
• Synthesis and carbon-13 nuclear magnetic resonance spectroscopy of 5,6-dihydro-2-methyl-1,4-oxathiin,trans-tetrahydro-1,4-benzoxathiin, 1,4-tetrahydro-[9,10]benzoxathiin, the 4-oxides, 4,4-dioxides and related acyclic compounds
  作者：Robert P. Rooney、John C. Dyer、Slayton A. Evans

  DOI：10.1002/mrc.1270160404

  日期：1981.8

  AbstractThe results of a 13C NMR spectral investigation involving 5,6‐dihydro‐1,4‐oxathiins, 1,4‐tetrahydro[9,10]benzoxathiin, trans‐tetrahydro‐1,4‐benzoxathiin, and the corresponding sulfoxides and sulfones are reported. An interpretation involving a dipolar structure with (2p→2p)π conjugation as opposed to (2p→3d)π interactions with the vinyloxy sulfides seems consistent with trends in the 13C NMR shifts. For the sulfoxides and sulfones, the substitutent‐induced chemical shift (SCS) effects at the β vinylic carbons (βSO and βSO2 effects) are considerably less than those at sp3 carbons. The γSO and γSO2 values at the sp2γ carbons indicate deshielding, in contrast to the shielding at the sp3 carbons.