phenanthrene-2-sulfonyl chloride | 63279-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: phenanthrene-2-sulfonyl chloride
• 英文别名: Phenanthren-2-sulfonylchlorid
• CAS: 63279-77-6
• 化学式: C₁₄H₉ClO₂S
• 分子量: 276.743
• InChiKey: JFFXMUNDLNNLFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenanthrene-2-sulfonyl chloride 在 吡啶 、 五氯化磷 、 硫酸 、 sodium carbonate 、 Petroleum ether 、 锌 作用下， 生成 2-(2-oxo-acenaphthen-1-ylidene)-phenanthro[2,1-b]thiophen-3-one
  参考文献：
  名称：

  Dutta; Chaudhury, Journal of the Indian Chemical Society, 1951, vol. 28, p. 169,174

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium phenanthrene-2-sulfonate 在 五氯化磷 、 三氯氧磷 作用下， 反应 1.0h， 以89%的产率得到phenanthrene-2-sulfonyl chloride
  参考文献：
  名称：

  Optimization of the synthesis of phenanthrene-2- and -3-sulfonyl chlorides

  摘要：

  Sulfonation of phenanthrene with sulfuric acid, followed by neutralization with sodium hydroxide, gave a mixture of isomeric sodium phenanthrenesulfonates in an overall yield of 83%. Sodium phenanthrene-2-, -3-, and -9-sulfonates were isolated in 17, 43, and 4% yield, respectively. Sulfonation of phenanthrene with ClSO3H or SO3 did not improve the yields of phenanthrene-2- and -3-sulfonic acids. Treatment of sodium phenanthrene-2- and -3-sulfonates with PCl5-POCl3 or SOCl2-DMF afforded the corresponding sulfonyl chlorides in 89 and 87 or 69 and 70% yield, respectively. Pure phenanthrene-2- and -3-sulfonyl chlorides were also synthesized in 27 and 51% yield by reaction of a mixture of 2- and 3-sulfonates with PCl5-POCl3.

  DOI：

  10.1134/s1070428012040148

文献信息

• Sandqvist, Justus Liebigs Annalen der Chemie, 1911, vol. 379, p. 87
  作者：Sandqvist

  DOI：——

  日期：——
• US4128586A
  申请人：——

  公开号：US4128586A

  公开（公告）日：1978-12-05
• Optimization of the synthesis of phenanthrene-2- and -3-sulfonyl chlorides
  作者：V. V. Russkikh、E. A. Khokhrina、V. V. Shelkovnikov

  DOI：10.1134/s1070428012040148

  日期：2012.4

  Sulfonation of phenanthrene with sulfuric acid, followed by neutralization with sodium hydroxide, gave a mixture of isomeric sodium phenanthrenesulfonates in an overall yield of 83%. Sodium phenanthrene-2-, -3-, and -9-sulfonates were isolated in 17, 43, and 4% yield, respectively. Sulfonation of phenanthrene with ClSO3H or SO3 did not improve the yields of phenanthrene-2- and -3-sulfonic acids. Treatment of sodium phenanthrene-2- and -3-sulfonates with PCl5-POCl3 or SOCl2-DMF afforded the corresponding sulfonyl chlorides in 89 and 87 or 69 and 70% yield, respectively. Pure phenanthrene-2- and -3-sulfonyl chlorides were also synthesized in 27 and 51% yield by reaction of a mixture of 2- and 3-sulfonates with PCl5-POCl3.
• Dutta; Chaudhury, Journal of the Indian Chemical Society, 1951, vol. 28, p. 169,174
  作者：Dutta、Chaudhury

  DOI：——

  日期：——