2-[(2-iodoethyl)disulfanyl]ethyl acetate | 899435-62-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[(2-iodoethyl)disulfanyl]ethyl acetate
• 英文别名: 2Acetoxyethyl 2iodoethyl disulfide；2-(2-iodoethyldisulfanyl)ethyl acetate
• CAS: 899435-62-2
• 化学式: C₆H₁₁IO₂S₂
• 分子量: 306.189
• InChiKey: QIVGOBOIFLJEIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(2-iodoethyl)disulfanyl]ethyl acetate 、 silver 3-formyl-4-hydroxyphenylphosphate 以 甲苯 为溶剂， 反应 12.0h， 以17%的产率得到Acetic acid 2-{2-[[2-(2-acetoxy-ethyldisulfanyl)-ethoxy]-(3-formyl-4-hydroxy-phenoxy)-phosphoryloxy]-ethyldisulfanyl}-ethyl ester
  参考文献：
  名称：

  Cell permeation of a Trypanosoma brucei aldolase inhibitor: Evaluation of different enzyme-labile phosphate protecting groups

  摘要：

  A series of four prodrugs directed against Trypanosoma brucei aldolase bearing various transient enzyme-labile phosphate protecting groups was developed. Herein, we describe the synthesis and evaluation of cell permeation of these prodrugs. The oxymethyl derivative was the most efficient prodrug with a good recovering of the free drug (IC50 = 20 mu M) and without any measurable cytotoxicity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.010
• 作为产物：
  描述：

  2-((2-hydroxyethyl)disulfanyl)ethyl acetate 在 吡啶 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 60.0h， 生成 2-[(2-iodoethyl)disulfanyl]ethyl acetate
  参考文献：
  名称：

  Cell permeation of a Trypanosoma brucei aldolase inhibitor: Evaluation of different enzyme-labile phosphate protecting groups

  摘要：

  A series of four prodrugs directed against Trypanosoma brucei aldolase bearing various transient enzyme-labile phosphate protecting groups was developed. Herein, we describe the synthesis and evaluation of cell permeation of these prodrugs. The oxymethyl derivative was the most efficient prodrug with a good recovering of the free drug (IC50 = 20 mu M) and without any measurable cytotoxicity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.010

文献信息

• Acyl iodides in organic synthesis. Reaction of acetyl iodide with thiols
  作者：M. G. Voronkov、O. Yu. Grigor’eva、N. N. Vlasova

  DOI：10.1134/s1070428011120013

  日期：2011.12

  The direction of reactions of acetyl iodide with aliphatic, aromatic, and heterocyclic thiols is determined by the thiol acidity and steric factors. Acetyl iodide reacted with aliphatic thiols, including trialkylsilyl-substituted derivatives R(CH2)(n)SH (R = Me, n = 3; R = Me3Si, n = 3; R = Et3Si, n = 2), to give the corresponding ethanethioates R(CH2)(n)SCOMe. Benzenethiol was oxidized with acetyl iodide to diphenyl disulfide. The reaction of acetyl iodide with 2-sulfanylethanol afforded 2-(2-iodoethyldisulfanyl)ethyl acetate as a result of three consecutive-parallel processes: acylation, iodination, and oxidation of the initial compound. 1,3-Benzothiazole-2-thiol reacted with acetyl iodide only at the nitrogen atom to give quaternary salt, whereas the SH group remained intact.