3-hydroxythietane 1-oxide | 24446-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环丁烷
• 英文名称: 3-hydroxythietane 1-oxide
• 英文别名: 3-Thietanol-1-oxid；3-Hydroxy-thietan-1-oxid；1-oxo-1λ⁴-thietan-3-ol；3-Hydroxythietane-1-oxide；1-oxothietan-3-ol
• CAS: 24446-67-1
• 化学式: C₃H₆O₂S
• mdl: MFCD30479647
• 分子量: 106.145
• InChiKey: PLSOVSDERKVYCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-羟基硫杂烷 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以64%的产率得到3-hydroxythietane 1-oxide
  参考文献：
  名称：

  Carbon-13 chemical shifts of 3-substituted thietanes, thietane 1-oxides and thietane 1,1-dioxides

  摘要：

  AbstractCarbon‐13 chemical shifts of the α‐ and β‐carbon atoms for 12 thietane 1,1‐dixides, 9 thietane 1‐oxides and 7 thietanes with a variety of 3‐substituents [H, CH(CO2Et)2, SEt, Br, SPh, Ph, Cl, NMe2, OH, OSiMe3, OAc, OEt] are correlated according to the nature of the sulfur atom (Y=sulfone, sulfoxide, sulfide) and the nature of the 3‐substituent (X) by the equations δα= aY+bX and δβ=aX+bY, where a and b are parameters characteristic of X and Y. One‐bond coupling constants [J(CH)] are reported for 21 compounds. The chemical shifts for the α‐ and the β‐carbon atoms of the sulfones show the ‘fore‐membered ring sulfone effect’ (α‐carbon unusually deshielded, β‐carbon unusually shielded), but the α‐carbon‐hydrogen coupling constants are similar to those of the sulfoxides and sulfides; the β‐carbon‐hydrogen coupling constants are sensitive to the nature of the substituent (X) but no special β‐effect is observed. Comparison of the chemical shifts of the α‐methylene carbon atoms of 3‐phenyl‐, 3‐(β‐naphthyl)‐ and 3‐(α‐thienyl)‐thietes with those of the coresponding sulfones also reveals the ‘four‐membered ring sulfone effect’ cis‐ and trans‐3‐Substituted thietane 1‐oxides may be distinguished by the greater downfield shift for the β‐carbon atom in the trans‐isomer.

  DOI：

  10.1002/mrc.1270180207

文献信息

• Carbon-13 chemical shifts of 3-substituted thietanes, thietane 1-oxides and thietane 1,1-dioxides
  作者：Donald C. Dittmer、Bhalchandra H. Patwardhan、John T. Bartholomew

  DOI：10.1002/mrc.1270180207

  日期：1982.2

  AbstractCarbon‐13 chemical shifts of the α‐ and β‐carbon atoms for 12 thietane 1,1‐dixides, 9 thietane 1‐oxides and 7 thietanes with a variety of 3‐substituents [H, CH(CO2Et)2, SEt, Br, SPh, Ph, Cl, NMe2, OH, OSiMe3, OAc, OEt] are correlated according to the nature of the sulfur atom (Y=sulfone, sulfoxide, sulfide) and the nature of the 3‐substituent (X) by the equations δα= aY+bX and δβ=aX+bY, where a and b are parameters characteristic of X and Y. One‐bond coupling constants [J(CH)] are reported for 21 compounds. The chemical shifts for the α‐ and the β‐carbon atoms of the sulfones show the ‘fore‐membered ring sulfone effect’ (α‐carbon unusually deshielded, β‐carbon unusually shielded), but the α‐carbon‐hydrogen coupling constants are similar to those of the sulfoxides and sulfides; the β‐carbon‐hydrogen coupling constants are sensitive to the nature of the substituent (X) but no special β‐effect is observed. Comparison of the chemical shifts of the α‐methylene carbon atoms of 3‐phenyl‐, 3‐(β‐naphthyl)‐ and 3‐(α‐thienyl)‐thietes with those of the coresponding sulfones also reveals the ‘four‐membered ring sulfone effect’ cis‐ and trans‐3‐Substituted thietane 1‐oxides may be distinguished by the greater downfield shift for the β‐carbon atom in the trans‐isomer.