<2-Nitro-4-<3-(trifluoromethyl)-3H-diazirin-3-yl>phenoxy>acetic acid methyl ester | 125680-83-3

• 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: <2-Nitro-4-<3-(trifluoromethyl)-3H-diazirin-3-yl>phenoxy>acetic acid methyl ester
• 英文别名: Methyl 2-[2-nitro-4-[3-(trifluoromethyl)diazirin-3-yl]phenoxy]acetate
• CAS: 125680-83-3
• 化学式: C₁₁H₈F₃N₃O₅
• 分子量: 319.197
• InChiKey: DSDXMTOGQJGUIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  <2-Nitro-4-<3-(trifluoromethyl)-3H-diazirin-3-yl>phenoxy>acetic acid methyl ester 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-<<<2-nitro-4-<3-(trifluoromethyl)-3H-diazirin-3-yl>phenoxy>acetyl>oxy>-2,5-pyrrolidinedione
  参考文献：
  名称：

  Syntheses of Nitro-Substituted Aryl Diazirines. An Entry to Chromogenic Carbene Precursors for Photoaffinity Labeling.

  摘要：

  合成了具有硝基和醚基取代基的3-苯基-3-三氟甲基-二氟啉衍生物，作为光标记产物的卡宾前驱体用于色谱检测。在甲醇或环己烷中光解二氟啉分别生成了分子间的O-H或C-H插入产物。光产物的光谱特性使得在大多数生物大分子的吸收可以忽略的光谱区域内进行光标记产物的检测成为可能。还制备了二氟啉的碳-14同位素类似物，用于微量标记产物的检测。这些硝基取代的芳基二氟啉应适用于广泛的光亲和标记研究，从示踪实验到通过HPLC配合光谱光度检测进行标记产物的制备分离。

  DOI：

  10.1248/cpb.42.826
• 作为产物：
  描述：

  3-(4-methoxyphenyl)-3-(trifluoromethyl)-3H-diazirine 在 (CH₃)SiI 、 cesium fluoride 、 sodium nitrite 、 thallium(III) trifluoroacetate 作用下， 以 乙腈 、 正戊烷 为溶剂， 反应 68.0h， 生成 <2-Nitro-4-<3-(trifluoromethyl)-3H-diazirin-3-yl>phenoxy>acetic 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

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：——
• Syntheses of Nitro-Substituted Aryl Diazirines. An Entry to Chromogenic Carbene Precursors for Photoaffinity Labeling.
  作者：Yasumaru HATANAKA、Makoto HASHIMOTO、Hitoshi NAKAYAMA、Yuichi KANAOKA

  DOI：10.1248/cpb.42.826

  日期：——

  3-Phenyl-3-trifluoromethyl-diazirine derivatives with nitro and alkoxy substituents on their aromatic ring have been synthesized as carbene precursors for chromogenic detection of photolabeled products. Photolysis of the diazirines in methanol or cyclohexane gave intermolecular O-H or C-H insertion products, respectively. Spectroscopic properties of the photoproducts are such that detection of photolabeled products may be performed in a spectral region where the absorption due to most biological macromolecules is negligible. A carbon-14 analog of the diazirine was also prepared for microscale detection of labeled products. These nitro-substituted aryl diazirines should be applicable to a wide range of photoaffinity labeling studies, from tracer experiments to preparative isolation of labeled products by HPLC with spectrophotometric detection.

  合成了具有硝基和醚基取代基的3-苯基-3-三氟甲基-二氟啉衍生物，作为光标记产物的卡宾前驱体用于色谱检测。在甲醇或环己烷中光解二氟啉分别生成了分子间的O-H或C-H插入产物。光产物的光谱特性使得在大多数生物大分子的吸收可以忽略的光谱区域内进行光标记产物的检测成为可能。还制备了二氟啉的碳-14同位素类似物，用于微量标记产物的检测。这些硝基取代的芳基二氟啉应适用于广泛的光亲和标记研究，从示踪实验到通过HPLC配合光谱光度检测进行标记产物的制备分离。
• 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.