thioacetic acid S-(3-cyanobenzyl) ester | 873463-98-0

• 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: thioacetic acid S-(3-cyanobenzyl) ester
• 英文别名: S-[(3-cyanophenyl)methyl] ethanethioate
• CAS: 873463-98-0
• 化学式: C₁₀H₉NOS
• 分子量: 191.254
• InChiKey: ZIDDXXRQRXOSEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  thioacetic acid S-(3-cyanobenzyl) ester 在 sodium hydroxide 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 5a-(3-cyanobenzylsulfanyl)dihydrobicyclomycin
  参考文献：
  名称：

  Fluorine-substituted dihydrobicyclomycins: Synthesis and biochemical and biological properties

  摘要：

  Many studies show that selective introduction of fluorine within pharmacological agents leads to improved activities. In this study, we determine the effects of aryl fluorine substitution in 5a-(benzylsulfanyl)-dihydrobicyclomycin (3) on the in vitro inhibition of Escherichia coli rho-dependent ATPase activity. Compound 3 is an analog of bicyclomycin (1), which is the only known selective inhibitor of rho, and I and 3 have comparable in vitro inhibitory activities. We demonstrate that aryl fluorine substitution of 3 leads to increase in inhibitory activity but that the beneficial effects due to fluorine were dependent upon the site and number of fluorine substituents. The bioactivitics are rationalized in terms of the bond moment created by the aryl fluoride bond within the 5a-aryl dihydrobicyclomycin-rho-binding pocket. Use of this hypothesis led to file design of dihydrobicyclomycin derivatives with superior in vitro rho inhibitory activities. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.075
• 作为产物：
  描述：

  3-氰基苄基溴 、 potassium thioacetate 以 丙酮 为溶剂， 以75%的产率得到thioacetic acid S-(3-cyanobenzyl) ester
  参考文献：
  名称：

  Fluorine-substituted dihydrobicyclomycins: Synthesis and biochemical and biological properties

  摘要：

  Many studies show that selective introduction of fluorine within pharmacological agents leads to improved activities. In this study, we determine the effects of aryl fluorine substitution in 5a-(benzylsulfanyl)-dihydrobicyclomycin (3) on the in vitro inhibition of Escherichia coli rho-dependent ATPase activity. Compound 3 is an analog of bicyclomycin (1), which is the only known selective inhibitor of rho, and I and 3 have comparable in vitro inhibitory activities. We demonstrate that aryl fluorine substitution of 3 leads to increase in inhibitory activity but that the beneficial effects due to fluorine were dependent upon the site and number of fluorine substituents. The bioactivitics are rationalized in terms of the bond moment created by the aryl fluoride bond within the 5a-aryl dihydrobicyclomycin-rho-binding pocket. Use of this hypothesis led to file design of dihydrobicyclomycin derivatives with superior in vitro rho inhibitory activities. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.075

文献信息

• Electron Transfer to Sulfides and Disulfides: Intrinsic Barriers and Relationship between Heterogeneous and Homogeneous Electron-Transfer Kinetics
  作者：Ana Belèn Meneses、Sabrina Antonello、Maria Carmen Arévalo、Concepcion Carmen González、Jadab Sharma、Andrea N. Wallette、Mark S. Workentin、Flavio Maran

  DOI：10.1002/chem.200700382

  日期：2007.9.28

  dissociative electron transfer (DET) which causes cleavage of the C(alkyl)--S or S--S bond. A generalized picture of how the intrinsic electron-transfer barrier depends on molecular features, ring substituents, and the presence of spacers between the frangible bond and aromatic groups was established. The reduction mechanism was found to undergo a progressive (and now predictable) transition between common

  在N，N-二甲基甲酰胺中，通过均相（氧化还原催化）和/或非均相（循环伏安法和卷积分析）电化学技术研究了一系列相关硫化物和二硫化物的电子受体性能。确定电子传输速率常数作为反应自由能的函数，并确定相应的固有势垒。评估了相关的热力学和动力学参数对取代基的依赖性。还就与还原二芳基二硫化物有关的相应数据相关地分析了动力学数据。所有研究的还原反应都是通过逐步解离电子转移（DET）进行的，该转移导致C（烷基）-S或SS键断裂。关于本征电子转移势垒如何取决于分子特征的概括图，确定了环取代基，以及在易碎键和芳族基团之间存在间隔基。发现该还原机理在普通的逐步DET和通过形成松散的自由基阴离子进行的DET之间经历了渐进的（并且现在是可预测的）转变。将本征壁垒与可用于ET的几类解离型和非解离型受体的可比结果进行了比较，这导致验证了Hush理论所预测的异构数据和均质数据之间的相关性。