菲-3-磺酰氯 | 24748-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 菲-3-磺酰氯
• 英文名称: Phenanthrene-3-sulphonyl chloride
• 英文别名: 3-Phenanthryl-sulfonsaeurechlorid；phenanthrene-3-sulfonyl chloride；Phenanthren-3-sulfonylchlorid
• CAS: 24748-51-4
• 化学式: C₁₄H₉ClO₂S
• 分子量: 276.743
• InChiKey: SXKCWOHHUDTWNV-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109 °C(Solv: benzene (71-43-2))
• 沸点：
  467.8±14.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

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：

  菲-3-磺酰氯 在 sodium hydroxide 、 氢溴酸 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 N^G-Phenanthrene-3-sulphonyl-L-arginine hydrobromide
  参考文献：
  名称：

  Ali, Syed Safdar; Echner, Hartmut; Khan, Khalid Mohammed, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 10, p. 1425 - 1433

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 五氯化磷 、 三氯氧磷 作用下， 生成 菲-3-磺酰氯
  参考文献：
  名称：

  Werner, Justus Liebigs Annalen der Chemie, 1902, vol. 321, p. 251

  摘要：

  DOI：

文献信息

• The discovery and structure—activity relationships of nonpeptide, low molecular weight antagonists selective for the endothelin ETB receptor
  作者：Ming Fai Chan、Adam Kois、Erik J. Verner、Bore G. Raju、Rosario S. Castillo、Chengde Wu、Ilya Okun、Fiona D. Stavros、V.N. Balaji

  DOI：10.1016/s0968-0896(98)80010-2

  日期：1998.12

  The systematic modification of the ETA selective N-(5-isoxazolyl)benzene-sulfonamide endothelin antagonists to give ETB selective antagonists is reported. The reversal in selectivity was brought about by substitution of the 4-position with aryl and substituted aryl groups. Of all the aromatic substituents studied, the para-tolyl group gave rise to the most active and selective ETB antagonist. Larger substituents caused a decrease in both ETB activity and selectivity. A similar trend was observed by substitution at the 5-position of the N-(5-isoxazolyl)-2-thiophenesulfonamide ETA receptor antagonists. The para-tolyl group was again found to be optimal for the ETB activity and selectivity. The structural features that were found to be favorable for binding to the ETB receptor, that is, the presence of a linear, conjugated pi-system of definite shape and size, have been successfully incorporated into the design of ETB selective polycyclic aromatic sulfonamides antagonists. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Nikolenko, Zhurnal Obshchei Khimii, 1956, vol. 26, p. 806;engl.Ausg.S.921
  作者：Nikolenko

  DOI：——

  日期：——
• 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.
• Sandqvist, Justus Liebigs Annalen der Chemie, 1909, vol. 369, p. 116
  作者：Sandqvist

  DOI：——

  日期：——
• Courtot; Kozertchouk, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1944, vol. 218, p. 973
  作者：Courtot、Kozertchouk

  DOI：——

  日期：——