m-Nitrophenyl decaoate | 61063-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: m-Nitrophenyl decaoate
• 英文别名: m-Nitrophenyldecanoat；3-Nitrophenyl decanoate；(3-nitrophenyl) decanoate
• CAS: 61063-38-5
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: DUSNZVOKUGGFJI-UHFFFAOYSA-N

物化性质

• 沸点：
  395.7±25.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  m-Nitrophenyl decaoate 在 Carbonate buffer 、 α-环糊精 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 正癸酸 、 间硝基苯酚
  参考文献：
  名称：

  Ester Cleavage by Cyclodextrins in Aqueous Dimethyl Sulfoxide Mixtures. Substrate Binding versus Transition State Binding

  摘要：

  The effects of DMSO on the kinetics of cleavage of m- and p-nitrophenyl alkanoates (mNPAlk and pNPAlk) by alpha- and beta-cyclodextrin (alpha-CD and beta-CD) in basic aqueous solution have been studied. For the two acetates addition of up to 60% (v/v) of DMSO increases rates but overall it has little effect on substrate binding, transition state binding, or the acceleration due to complexation. By contrast, in 50% (v/v) aqueous DMF these characteristics are greatly affected such that the normal difference in reactivity of the isomers is almost removed. The cleavage of mNPAlk and pNPAlk (C2 to C10) by the CDs in 60% (v/v) aqueous DMSO have very different chain length dependences for substrate binding and transition state binding, and there are significant changes from their behavior in water. Even though hydrophobic effects seem to be largely removed in 60% aqueous DMSO, and the difference between the reactivities of the isomers is reduced, reaction of mNPAlk proceeds through aryl group inclusion and that of pNPAlk through acyl group inclusion, as in water. The cleavage of m-tert-butylphenyl acetate is accelerated more in 60% (v/v) aqueous DMSO than in water because the solvent change weakens substrate binding more than transition state binding.

  DOI：

  10.1021/jo00104a014
• 作为产物：
  描述：

  正癸酸 、 间硝基苯酚 在 N,N'-二环己基碳二亚胺 作用下， 生成 m-Nitrophenyl decaoate
  参考文献：
  名称：

  Catalytic dipolar micelles. 3. Substrate and surfactant structural effects in the hydrolyses of substituted phenyl esters in presence and in absence of dipolar cationic micelles: mechanistic considerations

  摘要：

  DOI：

  10.1021/jo00425a020

文献信息

• Gadosy, Timothy A.; Tee, Oswald S., Journal of the Chemical Society. Perkin transactions II, 1994, # 4, p. 715 - 722
  作者：Gadosy, Timothy A.、Tee, Oswald S.

  DOI：——

  日期：——
• Catalytic dipolar micelles. 3. Substrate and surfactant structural effects in the hydrolyses of substituted phenyl esters in presence and in absence of dipolar cationic micelles: mechanistic considerations
  作者：Rina Shiffman、Mordechai Chevion、Jehoshua Katzhendler、Chaim Rav-Acha、Shalom Sarel

  DOI：10.1021/jo00425a020

  日期：1977.3
• Ester Cleavage by Cyclodextrins in Aqueous Dimethyl Sulfoxide Mixtures. Substrate Binding versus Transition State Binding
  作者：Oswald S. Tee、Charles Mazza、Rafael Lozano-Hemmer、Javier B. Giorgi

  DOI：10.1021/jo00104a014

  日期：1994.12

  The effects of DMSO on the kinetics of cleavage of m- and p-nitrophenyl alkanoates (mNPAlk and pNPAlk) by alpha- and beta-cyclodextrin (alpha-CD and beta-CD) in basic aqueous solution have been studied. For the two acetates addition of up to 60% (v/v) of DMSO increases rates but overall it has little effect on substrate binding, transition state binding, or the acceleration due to complexation. By contrast, in 50% (v/v) aqueous DMF these characteristics are greatly affected such that the normal difference in reactivity of the isomers is almost removed. The cleavage of mNPAlk and pNPAlk (C2 to C10) by the CDs in 60% (v/v) aqueous DMSO have very different chain length dependences for substrate binding and transition state binding, and there are significant changes from their behavior in water. Even though hydrophobic effects seem to be largely removed in 60% aqueous DMSO, and the difference between the reactivities of the isomers is reduced, reaction of mNPAlk proceeds through aryl group inclusion and that of pNPAlk through acyl group inclusion, as in water. The cleavage of m-tert-butylphenyl acetate is accelerated more in 60% (v/v) aqueous DMSO than in water because the solvent change weakens substrate binding more than transition state binding.