phenoxysulfonyl-carbamic acid methyl ester | 52200-01-8

• 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: phenoxysulfonyl-carbamic acid methyl ester
• 英文别名: Phenoxysulfonyl-carbamidsaeure-methylester；methyl N-phenoxysulfonylcarbamate
• CAS: 52200-01-8
• 化学式: C₈H₉NO₅S
• 分子量: 231.229
• InChiKey: HJFOUNNONKJPSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenoxysulfonyl-carbamic acid methyl ester 在 氘代盐酸 作用下， 以 氘代乙腈 为溶剂， 生成 甲醇 、 氨基甲酸甲酯 、 苯酚
  参考文献：
  名称：

  Mechanisms of Decomposition of Aryl N-(Methoxycarbonyl)sulfamates in Aqueous Media

  摘要：

  Rate constants and products are reported for the decomposition of aryl N-(methoxycarbonyl)sulfamates 1a-h (range) in aqueous solutions (pH 0-14) at 50 degrees C. The pK(a) values at 25 degrees C of 1a-h are 0.46-2.40. The pH-rate profiles of 1 indicate a rate law that includes three terms: two pH independent terms, k(a) in acid and k(p) around neutral pH, with k(a) > k(p), and a hydroxide ion dependent term, k(OH). In acid, product analysis reveals that both S-O (k(SO2)) and C-O (k(CO)) bond cleavage reactions are involved. From an analysis of beta(1g), solvent isotope effects, and solvent isotopic labeling of the products, it is concluded (a) that the C-O cleavage reaction involves protonation of the leaving group methanol and its expulsion from the dipolar intermediate ArOSO2N-CO-O+HCH3 and (b) that the S-O cleavage reaction may involve either an intra- or an intermolecular general acid-catalyzed decomposition of 1 or 1-, respectively. in contrast to k(a), the spontaneous hydrolysis reaction of 1(-), k(p), takes place exclusively via S-O bond fission. The k(OH) reaction of 1(-) is rationalized by OH- attack either at the carbonyl center (1b-h) or at the aromatic ring (1a). It is concluded that the -SO2NHCO- group may be viewed as an attractive phosphate analogue.

  DOI：

  10.1021/ja981014w
• 作为产物：
  描述：

  N-氯磺酰基氨基甲酸甲酯 、 苯酚 在 三乙胺 作用下， 以 乙醚 为溶剂， 生成 phenoxysulfonyl-carbamic acid methyl ester
  参考文献：
  名称：

  Graf,R., Chemische Berichte, 1963, vol. 96, p. 56 - 67

  摘要：

  DOI：

文献信息

• DE940292
  申请人：——

  公开号：——

  公开（公告）日：——
• Mechanisms of Decomposition of Aryl <i>N</i>-(Methoxycarbonyl)sulfamates in Aqueous Media
  作者：Patrick Blans、Alain Vigroux

  DOI：10.1021/ja981014w

  日期：1998.9.1

  Rate constants and products are reported for the decomposition of aryl N-(methoxycarbonyl)sulfamates 1a-h (range) in aqueous solutions (pH 0-14) at 50 degrees C. The pK(a) values at 25 degrees C of 1a-h are 0.46-2.40. The pH-rate profiles of 1 indicate a rate law that includes three terms: two pH independent terms, k(a) in acid and k(p) around neutral pH, with k(a) > k(p), and a hydroxide ion dependent term, k(OH). In acid, product analysis reveals that both S-O (k(SO2)) and C-O (k(CO)) bond cleavage reactions are involved. From an analysis of beta(1g), solvent isotope effects, and solvent isotopic labeling of the products, it is concluded (a) that the C-O cleavage reaction involves protonation of the leaving group methanol and its expulsion from the dipolar intermediate ArOSO2N-CO-O+HCH3 and (b) that the S-O cleavage reaction may involve either an intra- or an intermolecular general acid-catalyzed decomposition of 1 or 1-, respectively. in contrast to k(a), the spontaneous hydrolysis reaction of 1(-), k(p), takes place exclusively via S-O bond fission. The k(OH) reaction of 1(-) is rationalized by OH- attack either at the carbonyl center (1b-h) or at the aromatic ring (1a). It is concluded that the -SO2NHCO- group may be viewed as an attractive phosphate analogue.
• Graf,R., Chemische Berichte, 1963, vol. 96, p. 56 - 67
  作者：Graf,R.

  DOI：——

  日期：——