3-(4-bromobenzylthio)-propanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-bromobenzylthio)-propanoic acid
• 英文别名: 3-[(4-bromophenyl)methylsulfanyl]propanoic acid
• 化学式: C₁₀H₁₁BrO₂S
• mdl: MFCD04067657
• 分子量: 275.166
• InChiKey: WXXMLDYAADNICK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-bromobenzylthio)-propanoic acid 在 三氯化磷 作用下， 生成 BrC6H4CH2SCH2CH2C(O)Cl
  参考文献：
  名称：

  Synthesis, spectral characterization, electrochemical properties and antimicrobial screening of sulfur containing acylferrocenes

  摘要：

  Several known and eight new sulfur containing acylferrocenes of the general formula FcCO(CH2)(n)SR (where Fc = ferrocenyl, n = 1 or 2 and R = alkyl, 4-bromobenzyl or 2,6-dichlorobenzyl group) were synthesized in order to test their in vitro antimicrobial activity against 11 bacterial and three fungal/yeast strains. It has been shown that only four of the 14 ketones are completely inactive at the tested dose, while the activities of the other ones were noteworthy. All new compounds were well characterized by IR and NMR spectral data, and their electrochemical properties were investigated by cyclic voltammetry. The X-ray crystal structures of two representative ketones are also presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.03.002
• 作为产物：
  描述：

  对溴溴苄 、 3-巯基丙酸 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到3-(4-bromobenzylthio)-propanoic acid
  参考文献：
  名称：

  某些含硫酰基二茂铁的合成

  摘要：

   通过将二茂铁与相应羧酸的 原位 生成的酰基卤化物进行 Friedel-Crafts 酰化反应，可以高收率合成在其侧链中含有硫原子的 酰基二茂铁 （S-保护的巯基乙酸和α-和β-巯基丙酸衍生物）。

  DOI：

  10.1007/s007060170099

文献信息

• Synthesis of some Sulfur-Containing Acylferrocenes
  作者：Rastko D. Vukićević、Danijela Ilić、Zoran Ratković、Mirjana Vukićević

  DOI：10.1007/s007060170099

  日期：2001.5.21

   Acylferrocenes containing a sulfur atom within their side chain were synthesized in good yields by Friedel-Crafts acylation of ferrocene with in situ generated acyl halides from the corresponding carboxylic acids (S-protected derivatives of thioglicolic and α- and β-mercaptopropionic acids).

   通过将二茂铁与相应羧酸的 原位 生成的酰基卤化物进行 Friedel-Crafts 酰化反应，可以高收率合成在其侧链中含有硫原子的 酰基二茂铁 （S-保护的巯基乙酸和α-和β-巯基丙酸衍生物）。
• Synthesis, spectral characterization, electrochemical properties and antimicrobial screening of sulfur containing acylferrocenes
  作者：Danijela Ilić、Ivan Damljanović、Dragana Stevanović、Mirjana Vukićević、Niko Radulović、Volker Kahlenberg、Gerhard Laus、Rastko D. Vukićević

  DOI：10.1016/j.poly.2010.03.002

  日期：2010.5

  Several known and eight new sulfur containing acylferrocenes of the general formula FcCO(CH2)(n)SR (where Fc = ferrocenyl, n = 1 or 2 and R = alkyl, 4-bromobenzyl or 2,6-dichlorobenzyl group) were synthesized in order to test their in vitro antimicrobial activity against 11 bacterial and three fungal/yeast strains. It has been shown that only four of the 14 ketones are completely inactive at the tested dose, while the activities of the other ones were noteworthy. All new compounds were well characterized by IR and NMR spectral data, and their electrochemical properties were investigated by cyclic voltammetry. The X-ray crystal structures of two representative ketones are also presented. (C) 2010 Elsevier Ltd. All rights reserved.