(4S)-4-naphthalen-2-yl-1,3,2-dioxathiolane 2-oxide | 204581-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4S)-4-naphthalen-2-yl-1,3,2-dioxathiolane 2-oxide
• CAS: 204581-97-5
• 化学式: C₁₂H₁₀O₃S
• 分子量: 234.276
• InChiKey: VDSWDRZGUHPFPN-ZGTOLYCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4S)-4-naphthalen-2-yl-1,3,2-dioxathiolane 2-oxide 在 甲基丙二酸二甲酯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以9%的产率得到2-萘乙酮
  参考文献：
  名称：

  Reaction of 1,2-Cyclic Sulfites with Some Soft Nucleophiles. Formation of Enantiomerically Pure gamma-Lactones.

  摘要：

  The reaction between 1,2-cyclic sulfites and soft carbon centered nucleophiles has been investigated. For monosubstituted cyclic sulfites, the main products were gamma-lactones or acetoxy esters. For 1,2-disubstituted cyclic sulfites. cyclopropanes. carbonate and dioxolanes were the main products, A mechanistic rationale for the product formation is presented.

  DOI：

  10.3891/acta.chem.scand.52-0338
• 作为产物：
  描述：

  (S)-(+)-1-(2-萘基)-1,2-乙二醇 在 氯化亚砜 作用下， 以81%的产率得到(4S)-4-naphthalen-2-yl-1,3,2-dioxathiolane 2-oxide
  参考文献：
  名称：

  Nucleophilic Reactions between Cyclic 1,2-Sulfites and Chloride Ions.

  摘要：

  When cyclic 1,2-sulfites are ring opened by chloride ion, the chlorohydrins are formed with low regio and stereo-selectivity. The mechanisms involved in the process were investigated by measuring the stereochemical outcome of the reactions. The results showed that reversible inversion pathways (S(N)2 reactions) and a retention pathway (S(N)2i reaction) gave rise to the loss in ee in both the chlorohydrins and in the cyclic 1,2-sulfites.

  DOI：

  10.3891/acta.chem.scand.50-0832