Trifluoro-methanesulfonic acid 3-oxo-2,3-dihydro-1λ³-benzo[d][1,2]iodazol-1-yl ester | 214269-07-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoro-methanesulfonic acid 3-oxo-2,3-dihydro-1λ³-benzo[d][1,2]iodazol-1-yl ester
• 英文别名: (3-oxo-2H-1lambda3,2-benziodazol-1-yl) trifluoromethanesulfonate；(3-oxo-2H-1λ3,2-benziodazol-1-yl) trifluoromethanesulfonate
• CAS: 214269-07-5
• 化学式: C₈H₅F₃INO₄S
• 分子量: 395.098
• InChiKey: OBGPXDDREOYRON-UHFFFAOYSA-N

物化性质

• 熔点：
  110-115 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid 3-oxo-2,3-dihydro-1λ³-benzo[d][1,2]iodazol-1-yl ester 、 丙酰胺 以 乙腈 为溶剂， 反应 1.0h， 以51%的产率得到N-(3-Imino-3H-1λ³-benzo[d][1,2]iodoxol-1-yl)-propionamide; compound with trifluoro-methanesulfonic acid
  参考文献：
  名称：

  Structure and Chemistry of Hypervalent Iodine Heterocycles:  Acid-Catalyzed Rearrangement of Benziodazol-3-ones to 3-Iminiumbenziodoxoles

  摘要：

  New 1-substituted benziodazoles, namely, azide 7, tosylate 8, mesylate 9, and triflate 10, were prepared by the reaction of acetoxybenziodazole 3 with TMSN3, TsOH . H2O, MsOH, or TMSOTf, respectively. Reaction of triflate 10 with alcohols (methanol, ethanol, 2-propanol, and 2-adamantanol) afforded novel 1-alkoxy-3-iminiumbenziodoxoles 11a-d, while similar reactions with amides gave 1-amido-3-iminiumbenziodoxoles 12a-d in 51-89% yield. The structure of iminiumbenziodoxole 12b was established by a single-crystal X-ray analysis. The results of ab initio molecular orbital calculations on structures 3 and 11 are in good agreement with X-ray structural data. The calculation results indicate that the driving force of the novel rearrangement of benziodazoles to 3-iminiumbenziodoxoles is the greater thermodynamic stability of the N-protonated 3-iminobenziodoxoles relative to O-protonated benziodazol-3-ones by about 9.0 (MP2: 10.8) kcal/mol in the case of the acetoxy substituted 3 and 3d compounds and 15 kcal/mol (MP2: 13.5 kcal/mol) for the methoxy-substituted derivatives 11 and 13.

  DOI：

  10.1021/jo980745b
• 作为产物：
  描述：

  2-碘苯甲酰胺 在 过氧乙酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 Trifluoro-methanesulfonic acid 3-oxo-2,3-dihydro-1λ³-benzo[d][1,2]iodazol-1-yl ester
  参考文献：
  名称：

  Structure and Chemistry of Hypervalent Iodine Heterocycles:  Acid-Catalyzed Rearrangement of Benziodazol-3-ones to 3-Iminiumbenziodoxoles

  摘要：

  New 1-substituted benziodazoles, namely, azide 7, tosylate 8, mesylate 9, and triflate 10, were prepared by the reaction of acetoxybenziodazole 3 with TMSN3, TsOH . H2O, MsOH, or TMSOTf, respectively. Reaction of triflate 10 with alcohols (methanol, ethanol, 2-propanol, and 2-adamantanol) afforded novel 1-alkoxy-3-iminiumbenziodoxoles 11a-d, while similar reactions with amides gave 1-amido-3-iminiumbenziodoxoles 12a-d in 51-89% yield. The structure of iminiumbenziodoxole 12b was established by a single-crystal X-ray analysis. The results of ab initio molecular orbital calculations on structures 3 and 11 are in good agreement with X-ray structural data. The calculation results indicate that the driving force of the novel rearrangement of benziodazoles to 3-iminiumbenziodoxoles is the greater thermodynamic stability of the N-protonated 3-iminobenziodoxoles relative to O-protonated benziodazol-3-ones by about 9.0 (MP2: 10.8) kcal/mol in the case of the acetoxy substituted 3 and 3d compounds and 15 kcal/mol (MP2: 13.5 kcal/mol) for the methoxy-substituted derivatives 11 and 13.

  DOI：

  10.1021/jo980745b

文献信息

• trans Influences on Hypervalent Bonding of Arylλ3-Iodanes: Their Stabilities and Isodesmic Reactions of Benziodoxolones and Benziodazolones
  作者：Masahito Ochiai、Takuya Sueda、Kazunori Miyamoto、Paul Kiprof、Viktor V. Zhdankin

  DOI：10.1002/anie.200603055

  日期：2006.12.11
• Structure and Chemistry of Hypervalent Iodine Heterocycles:  Acid-Catalyzed Rearrangement of Benziodazol-3-ones to 3-Iminiumbenziodoxoles
  作者：Viktor V. Zhdankin、Ruslan M. Arbit、Benjamin J. Lynch、Paul Kiprof、Victor G. Young

  DOI：10.1021/jo980745b

  日期：1998.9.1

  New 1-substituted benziodazoles, namely, azide 7, tosylate 8, mesylate 9, and triflate 10, were prepared by the reaction of acetoxybenziodazole 3 with TMSN3, TsOH . H2O, MsOH, or TMSOTf, respectively. Reaction of triflate 10 with alcohols (methanol, ethanol, 2-propanol, and 2-adamantanol) afforded novel 1-alkoxy-3-iminiumbenziodoxoles 11a-d, while similar reactions with amides gave 1-amido-3-iminiumbenziodoxoles 12a-d in 51-89% yield. The structure of iminiumbenziodoxole 12b was established by a single-crystal X-ray analysis. The results of ab initio molecular orbital calculations on structures 3 and 11 are in good agreement with X-ray structural data. The calculation results indicate that the driving force of the novel rearrangement of benziodazoles to 3-iminiumbenziodoxoles is the greater thermodynamic stability of the N-protonated 3-iminobenziodoxoles relative to O-protonated benziodazol-3-ones by about 9.0 (MP2: 10.8) kcal/mol in the case of the acetoxy substituted 3 and 3d compounds and 15 kcal/mol (MP2: 13.5 kcal/mol) for the methoxy-substituted derivatives 11 and 13.