methyl 3-S-nitrosomercaptopropionate | 166667-92-1

• 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: methyl 3-S-nitrosomercaptopropionate
• 英文别名: Methyl 3-nitrososulfanylpropanoate；methyl 3-nitrososulfanylpropanoate
• CAS: 166667-92-1
• 化学式: C₄H₇NO₃S
• 分子量: 149.17
• InChiKey: IIPRVAJFOHHHGF-UHFFFAOYSA-N

物化性质

• 沸点：
  210.7±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  81
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-S-nitrosomercaptopropionate 生成 methyl 3-mercaptopropionate ion
  参考文献：
  名称：

  Nitroso group transfer from N-nitrososulfonamides to thiolate ions. Intrinsic reactivity

  摘要：

  The nitroso group transfer from N-nitrososulfonamides to thiolate ions was studied. Based on the results, the reaction rate is strongly dependent on the nature of the leaving group (alpha(1g) approximate to -1.30), but virtually independent of the basicity of the thiol (beta(nuc) approximate to 0-10)This dependence is ascribed to the presence of a nucleophile desolvation equilibrium (beta(d)) that is followed by the attack of the thiolate ion on the nitroso group (beta'(nuc)) via a concerted mechanism. The equilibrium constants for the loss of a nitroso group from a nitrosothiol and an N-nitrososulfonarni de were used to obtain the equilibrium constants for the different reactions involved. By using rate-equilibrium correlations, the parameters alpha(norm)(1g) ,beta(d), and beta('norm)(nuc) were obtained. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.060
• 作为产物：
  描述：

  3-巯基丙酸甲酯 在 氧化亚氮 作用下， 生成 methyl 3-S-nitrosomercaptopropionate
  参考文献：
  名称：

  Nitroso group transfer from N-nitrososulfonamides to thiolate ions. Intrinsic reactivity

  摘要：

  The nitroso group transfer from N-nitrososulfonamides to thiolate ions was studied. Based on the results, the reaction rate is strongly dependent on the nature of the leaving group (alpha(1g) approximate to -1.30), but virtually independent of the basicity of the thiol (beta(nuc) approximate to 0-10)This dependence is ascribed to the presence of a nucleophile desolvation equilibrium (beta(d)) that is followed by the attack of the thiolate ion on the nitroso group (beta'(nuc)) via a concerted mechanism. The equilibrium constants for the loss of a nitroso group from a nitrosothiol and an N-nitrososulfonarni de were used to obtain the equilibrium constants for the different reactions involved. By using rate-equilibrium correlations, the parameters alpha(norm)(1g) ,beta(d), and beta('norm)(nuc) were obtained. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.060

文献信息

• Barnett, D.Jonathan; Rios, Ana; Williams, D. Lyn H., Journal of the Chemical Society. Perkin transactions II, 1995, # 7, p. 1279 - 1282
  作者：Barnett, D.Jonathan、Rios, Ana、Williams, D. Lyn H.

  DOI：——

  日期：——
• Nitroso group transfer from N-nitrososulfonamides to thiolate ions. Intrinsic reactivity
  作者：C. Adam、L. García-Río、J.R. Leis、J.A. Moreira

  DOI：10.1016/j.tet.2006.06.060

  日期：2006.9

  The nitroso group transfer from N-nitrososulfonamides to thiolate ions was studied. Based on the results, the reaction rate is strongly dependent on the nature of the leaving group (alpha(1g) approximate to -1.30), but virtually independent of the basicity of the thiol (beta(nuc) approximate to 0-10)This dependence is ascribed to the presence of a nucleophile desolvation equilibrium (beta(d)) that is followed by the attack of the thiolate ion on the nitroso group (beta'(nuc)) via a concerted mechanism. The equilibrium constants for the loss of a nitroso group from a nitrosothiol and an N-nitrososulfonarni de were used to obtain the equilibrium constants for the different reactions involved. By using rate-equilibrium correlations, the parameters alpha(norm)(1g) ,beta(d), and beta('norm)(nuc) were obtained. (c) 2006 Elsevier Ltd. All rights reserved.