2-羟基-4-[3-(三氟甲基)-3H-二氮杂环丙烯-3-基]苯甲酸甲酯 | 165963-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-4-[3-(三氟甲基)-3H-二氮杂环丙烯-3-基]苯甲酸甲酯
• 英文名称: 2-Hydroxy-4-<3-(trifluoromethyl)-3H-diazirin-3-yl>benzoic acid methyl ester
• 英文别名: 2-Hydroxy-4-[3-(trifluoromethyl)-3H-diazirin-3-YL]benzoic acid, methyl ester；methyl 2-hydroxy-4-[3-(trifluoromethyl)diazirin-3-yl]benzoate
• CAS: 165963-72-4
• 化学式: C₁₀H₇F₃N₂O₃
• 分子量: 260.172
• InChiKey: UESDLZIPGDGBBE-UHFFFAOYSA-N

物化性质

• 熔点：
  47-49°C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-羟基-4-[3-(三氟甲基)-3H-二氮杂环丙烯-3-基]苯甲酸甲酯 在 chloroamine-T 、 sodium iodide 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以83%的产率得到2-Hydroxy-5-iodo-4-<3-(trifluoromethyl)-3H-diazirin-3-yl>benzoic acid methyl ester
  参考文献：
  名称：

  A Novel Family of Aromatic Diazirines for Photoaffinity Labeling

  摘要：

  A series Of simple methods for modifying diazirines bearing an aromatic ring has been accomplished. This first versatile approach involving direct substitution on the aromatic ring of diazirines has been achieved by means of the aromatic thallation of (alkoxyphenyl)diazirines. Introduction of the thallium moiety was successfully followed by nitration, iodination, or palladium-catalyzed carbonylation to give a family of substituted aryldiazirines useful for photolabeling. For instance, diazirines labeled with a nitro group can be detected by spectrophotometric methods, and those labeled with an iodo group can be useful in tracer experiments. The (methoxyphenyl)diazirines were also found to be stable under certain demethylation conditions, thus providing a potential source of diazirines with modifiable phenol hydroxyl groups. By means of this approach, a spacer arm to link diazirines with ligands was readily introduced. Radioactive diazirines labeled with carbon-14 or tritium were also prepared using this method. All the new diazirines were derived from a pair of simple (methoxyphenyl)diazirines. The ease of derivatization of the (alkoxyphenyl)diazirines described here may offer a practical approach to simplify the time-consuming methods currently used for diazirine synthesis.

  DOI：

  10.1021/jo00081a017
• 作为产物：
  描述：

  3-(3-甲氧基苯基)-3-(三氟甲基)双吖丙啶 在 magnesium oxide 、 三溴化硼 、 lithium chloride 、 palladium dichloride 、 thallium(III) trifluoroacetate 作用下， 以 二氯甲烷 为溶剂， 反应 67.5h， 生成 2-羟基-4-[3-(三氟甲基)-3H-二氮杂环丙烯-3-基]苯甲酸甲酯
  参考文献：
  名称：

  A Novel Family of Aromatic Diazirines for Photoaffinity Labeling

  摘要：

  A series Of simple methods for modifying diazirines bearing an aromatic ring has been accomplished. This first versatile approach involving direct substitution on the aromatic ring of diazirines has been achieved by means of the aromatic thallation of (alkoxyphenyl)diazirines. Introduction of the thallium moiety was successfully followed by nitration, iodination, or palladium-catalyzed carbonylation to give a family of substituted aryldiazirines useful for photolabeling. For instance, diazirines labeled with a nitro group can be detected by spectrophotometric methods, and those labeled with an iodo group can be useful in tracer experiments. The (methoxyphenyl)diazirines were also found to be stable under certain demethylation conditions, thus providing a potential source of diazirines with modifiable phenol hydroxyl groups. By means of this approach, a spacer arm to link diazirines with ligands was readily introduced. Radioactive diazirines labeled with carbon-14 or tritium were also prepared using this method. All the new diazirines were derived from a pair of simple (methoxyphenyl)diazirines. The ease of derivatization of the (alkoxyphenyl)diazirines described here may offer a practical approach to simplify the time-consuming methods currently used for diazirine synthesis.

  DOI：

  10.1021/jo00081a017

文献信息

• Hatanaka Yasumaru, Hashimoto Makoto, Kurihara Hiroko, Nakayama Hitoshi, K+, J. Org. Chem, 59 (1994) N 2, S 383-387
  作者：Hatanaka Yasumaru, Hashimoto Makoto, Kurihara Hiroko, Nakayama Hitoshi, K+

  DOI：——

  日期：——
• A Novel Family of Aromatic Diazirines for Photoaffinity Labeling
  作者：Yasumaru Hatanaka、Makoto Hashimoto、Hiroko Kurihara、Hitoshi Nakayama、Yuichi Kanaoka

  DOI：10.1021/jo00081a017

  日期：1994.1

  A series Of simple methods for modifying diazirines bearing an aromatic ring has been accomplished. This first versatile approach involving direct substitution on the aromatic ring of diazirines has been achieved by means of the aromatic thallation of (alkoxyphenyl)diazirines. Introduction of the thallium moiety was successfully followed by nitration, iodination, or palladium-catalyzed carbonylation to give a family of substituted aryldiazirines useful for photolabeling. For instance, diazirines labeled with a nitro group can be detected by spectrophotometric methods, and those labeled with an iodo group can be useful in tracer experiments. The (methoxyphenyl)diazirines were also found to be stable under certain demethylation conditions, thus providing a potential source of diazirines with modifiable phenol hydroxyl groups. By means of this approach, a spacer arm to link diazirines with ligands was readily introduced. Radioactive diazirines labeled with carbon-14 or tritium were also prepared using this method. All the new diazirines were derived from a pair of simple (methoxyphenyl)diazirines. The ease of derivatization of the (alkoxyphenyl)diazirines described here may offer a practical approach to simplify the time-consuming methods currently used for diazirine synthesis.