Acetic acid 3-oxo-2,3-dihydro-1λ³-benzo[d][1,2]iodazol-1-yl ester | 193882-91-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: Acetic acid 3-oxo-2,3-dihydro-1λ³-benzo[d][1,2]iodazol-1-yl ester
• 英文别名: (3-oxo-2H-1$l^{3},2-benziodazol-1-yl) acetate；(3-oxo-2H-1λ3,2-benziodazol-1-yl) acetate
• CAS: 193882-91-6
• 化学式: C₉H₈INO₃
• 分子量: 305.072
• InChiKey: YSJTUDMXQVOXKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetic acid 3-oxo-2,3-dihydro-1λ³-benzo[d][1,2]iodazol-1-yl ester 以 乙腈 为溶剂， 反应 1.0h， 生成 1-methoxy-1λ3,2-benziodoxol-3-imine;trifluoromethanesulfonic 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-碘苯甲酸 在 草酰氯 、 氨 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 Acetic acid 3-oxo-2,3-dihydro-1λ³-benzo[d][1,2]iodazol-1-yl ester
  参考文献：
  名称：

  铼催化C（SP的脱氢烯3）-H键与高价碘（III）的试剂†

  摘要：

  通过合并rh催化与丙氨酸衍生的高价碘（III）试剂，本文公开了C（sp 3）-H键的脱氢烯化反应。因此，环状和非环状醚，甲苯衍生物，环烷烃和腈都以区域和立体选择性的方式成功地被烯基化。

  DOI：

  10.1039/c5ob00619h

文献信息

• Structure and Chemistry of Acetoxybenziodazole. Acid-Catalyzed Rearrangement of Benziodazoles to 3-Iminobenziodoxoles
  作者：Viktor V. Zhdankin、Ruslan M. Arbit、Marc McSherry、Brian Mismash、Victor G. Young

  DOI：10.1021/ja971606z

  日期：1997.8.1
• 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
• Rhenium-catalyzed dehydrogenative olefination of C(sp³)–H bonds with hypervalent iodine(<scp>iii</scp>) reagents
  作者：Haidong Gu、Congyang Wang

  DOI：10.1039/c5ob00619h

  日期：——

  dehydrogenative olefination of C(sp3)–H bonds is disclosed here, by merging rhenium catalysis with an alanine-derived hypervalent iodine(III) reagent. Thus, cyclic and acyclic ethers, toluene derivatives, cycloalkanes, and nitriles are all successfully alkenylated in a regio- and stereoselective manner.

  通过合并rh催化与丙氨酸衍生的高价碘（III）试剂，本文公开了C（sp 3）-H键的脱氢烯化反应。因此，环状和非环状醚，甲苯衍生物，环烷烃和腈都以区域和立体选择性的方式成功地被烯基化。
• 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.