4-[3-(三氟甲基)-3H-双吖丙啶-3-基]苯酚 | 156824-51-0

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物 - 酚及其卤化、磺化、硝化或亚硝化衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-[3-(三氟甲基)-3H-双吖丙啶-3-基]苯酚
• 英文名称: 3-(4-hydroxyphenyl)-3-trifluoromethyldiazirine
• 英文别名: 4-[3-(trifluoromethyl)diazirin-3-yl]phenol
• CAS: 156824-51-0
• 化学式: C₈H₅F₃N₂O
• 分子量: 202.136
• InChiKey: PHKPMDDDGUKFFT-UHFFFAOYSA-N

物化性质

• 沸点：
  242.3±50.0℃ (760 Torr)
• 密度：
  1.54±0.1 g/cm3 (20 ºC 760 Torr)
• 闪点：
  100.3±30.1℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[3-(三氟甲基)-3H-双吖丙啶-3-基]苯酚 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 11.0h， 生成 <4-(2,2,2-trifluoro-1-methoxyethyl)phenoxy>acetic acid methyl ester
  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 作用下， 以 正戊烷 为溶剂， 反应 65.0h， 以26%的产率得到4-[3-(三氟甲基)-3H-双吖丙啶-3-基]苯酚
  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

• Photoaffinity-labeled sphingomyelin analogs and processes thereof
  申请人：Katsumura Shigeo

  公开号：US20050182265A1

  公开（公告）日：2005-08-18

  A photoaffinity-labeled sphingomyelin analog of the following formula: wherein R 1 is C 1-20 alkylene group, R 5 is C 1-20 alkyl group, aryl group or C 1-6 alkyl group substituted by aryl group, Z is photoaffinity-labeled group and Me is methyl group, or an optically active compound thereof.

  以下公式的光亲和标记鞘磷脂类似物： 其中R1是C1-20烷基基团，R5是C1-20烷基基团、芳基基团或由芳基基团取代的C1-6烷基基团，Z是光亲和标记基团，而Me是甲基基团， 或者是其光学活性化合物。
• Sphingomyelin analogues and a process for preparation thereof
  申请人：Katsumura Shigeo

  公开号：US20060008518A1

  公开（公告）日：2006-01-12

  A sphingomyelin analog represented by the following formula wherein R 1 is C 1-20 alkyl group, R 2 is C 1-20 alkyl group, aryl group or C 1-6 alkyl group substituted by aryl group, and Z is photoaffinity-labeled group, or its optically active compound.

  一个由以下公式表示的鞘磷脂类似物，其中R1是C1-20烷基团，R2是C1-20烷基团、芳基团或芳基取代的C1-6烷基团，Z是光亲和标记基团，或其光学活性化合物。
• Useful Method for Direct Introduction of the Photoaffinity 3-(4-Hydroxyphenyl)-3-trifluoromethyldiazirine Group
  作者：Toshihiko Shigenari、Toshikazu Hakogi、Shigeo Katsumura

  DOI：10.1246/cl.2004.594

  日期：2004.5

  A convergent and efficient preparation method of the photoaffinity 3-(4-alkoxyphenyl)-3-trifluoromethyldiazirine derivatives was established by direct introduction of the photoaffinity group utilizing the Mitsunobu reaction.

  利用 Mitsunobu 反应直接引入光亲和基团，建立了一种趋同、高效的光亲和 3-(4-烷氧基苯基)-3-三氟甲基二氮丙啶衍生物的制备方法。
• Syntheses and properties of photoactivatable sugar derivatives designed to probe the sugar-binding site of melibiose permease
  作者：Yves Ambroise、Charles Mioskowski、Gérard Leblanc、Bernard Rousseau

  DOI：10.1016/s0960-894x(00)00180-3

  日期：2000.5

  Three new photoreactive sugar analogues bearing an azido, a diazonium salt or a diazirine group as the photophore as well as a tritium atom were developed. Two of these new photoactivatable compounds gave excellent preliminary results, with a high affinity for the melibiose permease of Escherichia coli. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of fluorescent and photoaffinity-labeled derivatives of bisphenol A and their inhibitory activity toward hypoxic expression of erythropoietin
  作者：Nobuhiro Maezawa、Hiroshi Tsuchikawa、Shigeo Katsumura、Tomoko Kubo、Susumu Imaoka

  DOI：10.1016/j.bmcl.2007.07.007

  日期：2007.9

  Bisphenol A derivatives, possessing a fluorescent dye and a photo-reactive group, were synthesized from bisphenol A, and the inhibitory activity of the derivatives was evaluated against hypoxic response. The synthesized derivatives were found to inhibit the hypoxic expression of erythropoietin in Hep3B cells as well as bisplienol A. (c) 2007 Elsevier Ltd. All rights reserved.