2-(3-methyl-4-nitroisoxazol-5-yl)-1-phenylethanesulfonic acid | 1229422-20-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-(3-methyl-4-nitroisoxazol-5-yl)-1-phenylethanesulfonic acid
• 英文别名: 3-Methyl-4-nitro-I+/--phenyl-5-isoxazoleethanesulfonic acid；2-(3-methyl-4-nitro-1,2-oxazol-5-yl)-1-phenylethanesulfonic acid
• CAS: 1229422-20-1
• 化学式: C₁₂H₁₂N₂O₆S
• 分子量: 312.303
• InChiKey: MVSLKGJDTJSTSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-styryl-4-nitro-3-methylisoxazole 在 sodium hydrogensulfite 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 36.0h， 以99%的产率得到2-(3-methyl-4-nitroisoxazol-5-yl)-1-phenylethanesulfonic acid
  参考文献：
  名称：

  开发一种用于将亚硫酸氢盐添加到亲电子烯烃中的温和程序

  摘要：

  由于所需条件的苛刻性，活化烯烃的磺酰化是重要但尚未探索的反应。我们已经确定了允许烯烃与等摩尔量的亚硫酸氢盐在室温下反应的方法。

  DOI：

  10.1002/adsc.201000543

文献信息

• [EN] A METHOD FOR PREPARING SULFUR-CONTAINING COMPOUNDS<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE COMPOSÉS CONTENANT DU SOUFRE
  申请人：ROYAL COLLEGE OF SURGEONS IE

  公开号：WO2010066450A1

  公开（公告）日：2010-06-17

  The invention provides a method for preparing sulfur-containing compounds, the method comprising reacting a donor compound comprising at least one sulfur having at least one lone pair of electrons, with an acceptor compound; wherein the reaction occurs in the presence of an amine, optionally an amine catalyst, capable of activating the sulfur having at least one lone pair of electrons; and wherein the reaction occurs via the formation of an transient intermediate species, optionally a transient intermediate species, between the amine, optionally the amine catalyst and the donor compound; and wherein the donor compound is selected from the group consisting of a sulfurous acid, a sulfenic acid and a sulfinic acid or a salt, ester or amide of a sulfurous acid, a sulfenic acid and a sulfinic acid. The invention also provides sulfur-containing compounds of the formula: wherein R is selected from: (a) 1 -(4-Nitro-phenyl)-3-oxo-3-phenyl-propane; (b) 2-(3-Methyl-4-nitro-isoxazol-5-yl)-1 -phenyl-ethane; (c) 1-(4-Methoxy-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; (d) 2-(3-Methyl-4-nitro-isoxazol-5-yl)-1-(4-nitro-phenyl)-ethane; (e) 1-(4-Fluoro-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; (f) 1 -(4-Chloro-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; and (g) 3-Oxo-cyclohexane. Finally, the invention provides use of chiral sulfur-containing compounds obtainable by the above-mentioned method or chiral sulfur-containing compounds as mentioned above for the resolution of racemic mixtures of amines.

  该发明提供了一种制备含硫化合物的方法，该方法包括将包含至少一个硫原子且至少一个孤对电子的给体化合物与受体化合物反应；其中，在胺的存在下进行反应，可选地，在能够激活至少一个硫原子具有至少一个孤对电子的胺的存在下进行反应；反应通过形成瞬态中间体物种进行，可选地，通过胺、可选地胺催化剂和给体化合物之间的瞬态中间体物种进行反应；给体化合物选自包括亚硫酸、亚硫酸和亚砜酸或亚硫酸、亚硫酸和亚砜酸的盐、酯或酰胺的群；该发明还提供了符合以下公式的含硫化合物：其中R选自：(a) 1-(4-硝基苯基)-3-氧代-3-苯基-丙烷；(b) 2-(3-甲基-4-硝基异噁唑-5-基)-1-苯基-乙烷；(c) 1-(4-甲氧基苯基)-2-(3-甲基-4-硝基异噁唑-5-基)-乙烷；(d) 2-(3-甲基-4-硝基异噁唑-5-基)-1-(4-硝基苯基)-乙烷；(e) 1-(4-氟苯基)-2-(3-甲基-4-硝基异噁唑-5-基)-乙烷；(f) 1-(4-氯苯基)-2-(3-甲基-4-硝基异噁唑-5-基)-乙烷；和(g) 3-氧代环己烷。最后，该发明提供了通过上述方法获得的手性含硫化合物或上述提到的手性含硫化合物用于分离胺的外消旋混合物。
• Method for Preparing Sulfur-Containing Compounds
  申请人：Mauro Adamo

  公开号：US20120029197A1

  公开（公告）日：2012-02-02

  The invention provides a method for preparing sulfur-containing compounds, the method comprising reacting a donor compound comprising at least one sulfur having at least one lone pair of electrons, with an acceptor compound; wherein the reaction occurs in the presence of an amine, optionally an amine catalyst, capable of activating the sulfur having at least one lone pair of electrons; and wherein the reaction occurs via the formation of an transient intermediate species, optionally a transient intermediate species, between the amine, optionally the amine catalyst and the donor compound; and wherein the donor compound is selected from the group consisting of a sulfurous acid, a sulfenic acid and a sulfinic acid or a salt, ester or amide of a sulfurous acid, a sulfenic acid and a sulfinic acid. The invention also provides sulfur-containing compounds of the formula: wherein R is selected from: (a) 1-(4-Nitro-phenyl)-3-oxo-3-phenyl-propane; (b) 2-(3-Methyl-4-nitro-isoxazol-5-yl)-1-phenyl-ethane; (c) 1-(4-Methoxy-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; (d) 2-(3-Methyl-4-nitro-isoxazol-5-yl)-1-(4-nitro-phenyl)-ethane; (e) 1-(4-Fluoro-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; (f) 1-(4-Chloro-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; and (g) 3-Oxo-cyclohexane. Finally, the invention provides use of chiral sulfur-containing compounds obtainable by the above-mentioned method or chiral sulfur-containing compounds as mentioned above for the resolution of racemic mixtures of amines.
• Development of a Mild Procedure for the Addition of Bisulfite to Electrophilic Olefins
  作者：Francesco Fini、Murali Nagabelli、Mauro F. A. Adamo

  DOI：10.1002/adsc.201000543

  日期：2010.12.17

  The sulfonylation of activated alkenes is an important yet unexplored reaction due to the harshness of conditions required. We have identified a procedure which allowed the reaction of alkenes with equimolar amounts of bisulfite at room temperature.

  由于所需条件的苛刻性，活化烯烃的磺酰化是重要但尚未探索的反应。我们已经确定了允许烯烃与等摩尔量的亚硫酸氢盐在室温下反应的方法。