二(4-羟基-1-萘基)二硫醚 | 302938-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 二(4-羟基-1-萘基)二硫醚
• 英文名称: di(4-hydroxy-1-naphthyl)disulfide
• 英文别名: 4,4'-disulfanediyl-di-[1]naphthol；Bis-(4-hydroxy-naphthyl-(1))-disulfid；4,4'-Disulfandiyl-di-[1]naphthol；4.4'-Dioxy-(1.1'-dinaphthyldisulfid)；4-[(4-Hydroxynaphthalen-1-yl)disulfanyl]naphthalen-1-ol
• CAS: 302938-42-7
• 化学式: C₂₀H₁₄O₂S₂
• 分子量: 350.462
• InChiKey: DDUDYBISTLEGSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二(4-羟基-1-萘基)二硫醚 、 2,3,4-三-O-乙酰基-β-D-吡喃木糖基三氯乙酰亚胺酸酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以78%的产率得到bis[4-(2,3,4-tri-O-acetyl-β-D-xylopyranoside)-1-naphthyl]disulfide
  参考文献：
  名称：

  Effects of oxygen–sulfur substitution on glycosaminoglycan-priming naphthoxylosides

  摘要：

  Three series of sulfur-containing analogs to the selectively antiproliferative 2-(6-hydroxynaphthyl) beta-D-xylopyranoside were synthesized and their biological properties investigated. A short, general route to hydroxynaphthyl disulfides from dihydroxy-naphthalenes was developed to utilize the disulfide bond as a sulfur-selective protecting group to enable the orthogonal protection of hydroxyls and thiols. The results indicate that hydrophobic, uncharged oxygen-sulfur substituted naphthoxylosides are taken up by calls and initiate priming of GAG chains to a greater extent compared to the oxygen analogs. No correlation between priming ability and antiproliferative activity was observed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.008
• 作为产物：
  描述：

  4-thiocyanatonaphthalen-1-ol 在 盐酸 、 乙醇 、 双氧水 、 锌 作用下， 生成 二(4-羟基-1-萘基)二硫醚
  参考文献：
  名称：

  Kaufmann; Liepe, Berichte der Deutschen Pharmazeutischen Gesellschaft, vol. 33, p. 148

  摘要：

  DOI：

文献信息

• Airan; Shah, Journal of the Indian Chemical Society, 1945, vol. 22, p. 359,361
  作者：Airan、Shah

  DOI：——

  日期：——
• Zincke; Ruppersberg, Chemische Berichte, 1915, vol. 48, p. 123
  作者：Zincke、Ruppersberg

  DOI：——

  日期：——
• Kaufmann; Liepe, Berichte der Deutschen Pharmazeutischen Gesellschaft, vol. 33, p. 148
  作者：Kaufmann、Liepe

  DOI：——

  日期：——
• US4156764A
  申请人：——

  公开号：US4156764A

  公开（公告）日：1979-05-29
• Effects of oxygen–sulfur substitution on glycosaminoglycan-priming naphthoxylosides
  作者：Mårten Jacobsson、Katrin Mani、Ulf Ellervik

  DOI：10.1016/j.bmc.2007.05.008

  日期：2007.8

  Three series of sulfur-containing analogs to the selectively antiproliferative 2-(6-hydroxynaphthyl) beta-D-xylopyranoside were synthesized and their biological properties investigated. A short, general route to hydroxynaphthyl disulfides from dihydroxy-naphthalenes was developed to utilize the disulfide bond as a sulfur-selective protecting group to enable the orthogonal protection of hydroxyls and thiols. The results indicate that hydrophobic, uncharged oxygen-sulfur substituted naphthoxylosides are taken up by calls and initiate priming of GAG chains to a greater extent compared to the oxygen analogs. No correlation between priming ability and antiproliferative activity was observed. (c) 2007 Elsevier Ltd. All rights reserved.