2-碘-4-[3-(三氟甲基)-3H-二氮杂环丙烯-3-基]苄醇 | 197968-46-0

• 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-碘-4-[3-(三氟甲基)-3H-二氮杂环丙烯-3-基]苄醇
• 英文名称: [2-iodo-4-(3-trifluoromethyl-3H-diazirin-3-yl)phenyl]methanol
• 英文别名: 2-iodo-[4-(3-trifluoromethyl)-3H-diazirin-3-yl]benzyl alcohol；2-Iodo-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzyl Alcohol；[2-iodo-4-[3-(trifluoromethyl)diazirin-3-yl]phenyl]methanol
• CAS: 197968-46-0
• 化学式: C₉H₆F₃IN₂O
• 分子量: 342.059
• InChiKey: RRDFFESOQHBLLK-UHFFFAOYSA-N

物化性质

• 沸点：
  352.7±52.0 °C(Predicted)
• 密度：
  2.08±0.1 g/cm3(Predicted)
• 溶解度：
  二氯甲烷、乙醚、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-碘-4-[3-(三氟甲基)-3H-二氮杂环丙烯-3-基]苄醇 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 4-[3-(三氟甲基)-3H-双吖丙啶-3-基]苄醇
  参考文献：
  名称：

  Consequences of Affinity in Heterogeneous Catalytic Reactions:  Highly Chemoselective Hydrogenolysis of Iodoarenes

  摘要：

  The catalytic hydrodeibdination reaction using molecular hydrogen and Pd/C has been revisited. It is shown, for the first time, that the chemoselectivity of this reaction is controlled by the high affinity of the iodinated compound for the catalyst. This reaction is compatible with most easily reducible functional groups (nitro, aldehyde, olefin, etc:). Using this reaction, the first general method for tritium labeling of 3-(triflubromethyl)-3-phenyldiazirine is described.

  DOI：

  10.1021/jo0012243
• 作为产物：
  描述：

  4-[3-(三氟甲基)-3H-双吖丙啶-3-基]苄醇 在 三氟甲磺酸 、 三氟乙酸 、 thallium(III) trifluoroacetate 、 sodium iodide 作用下， 以 水 为溶剂， 以64 %的产率得到2-碘-4-[3-(三氟甲基)-3H-二氮杂环丙烯-3-基]苄醇
  参考文献：
  名称：

  Different chemical proteomic approaches to identify the targets of lapatinib

  摘要：

  DOI：

  10.1080/14756366.2023.2183809
• 作为试剂：
  描述：

  3-已炔-1-醇 在 palladium on activated charcoal 吡啶 、 氢气 、 三乙胺 、 2-碘-4-[3-(三氟甲基)-3H-二氮杂环丙烯-3-基]苄醇 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.17h， 生成 3-己烯-1-醇苯甲酸酯
  参考文献：
  名称：

  Consequences of Affinity in Heterogeneous Catalytic Reactions:  Highly Chemoselective Hydrogenolysis of Iodoarenes

  摘要：

  The catalytic hydrodeibdination reaction using molecular hydrogen and Pd/C has been revisited. It is shown, for the first time, that the chemoselectivity of this reaction is controlled by the high affinity of the iodinated compound for the catalyst. This reaction is compatible with most easily reducible functional groups (nitro, aldehyde, olefin, etc:). Using this reaction, the first general method for tritium labeling of 3-(triflubromethyl)-3-phenyldiazirine is described.

  DOI：

  10.1021/jo0012243

文献信息

• Synthesis and Enzymatic Phosphorylation of a Photoactivatable Dolichol Analogue
  作者：D. Grassi、V. Lippuner、M. Aebi、J. Brunner、A. Vasella

  DOI：10.1021/ja9721677

  日期：1997.11.1

  The synthesis of the photochemical probes 6 and 7 is described. These photoprobes are analogues of dolichol and dolichol phosphate, obligatory intermediates in the N-linked glycosylation pathway in the endoplasmic reticulum. The synthesis of 6 and 7 follows a new strategy. It involves the sequential alkylation of a monoterpenoid hydroxysulfonyl dianion with allyl chlorides. The photoreactive group

  描述了光化学探针 6 和 7 的合成。这些光探针是多萜醇和多萜醇磷酸盐的类似物，是内质网中 N-连接糖基化途径中的必需中间体。6 和 7 的合成遵循一个新的策略。它涉及单萜类羟基磺酰基二价阴离子与烯丙基氯的顺序烷基化。光反应性基团 3-（三氟甲基）-3-芳基二氮丙啶与完全组装的聚异戊二烯链的 β-异戊二烯基单元的羟基化甲基相连。可光活化的多萜醇类似物 6 是酵母膜多萜醇激酶的底物，酵母膜是 N-连接糖基化途径中必不可少的酶。
• 2-(Tributylstannyl)-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzyl Alcohol: A Building Block for Photolabeling and Crosslinking Reagents of Very High Specific Radioactivity
  作者：Thomas Weber、Josef Brunner

  DOI：10.1021/ja00116a013

  日期：1995.3

  A general approach for the synthesis of novel, radioiodinated photolabeling and cross-linking reagents at no-carrier-added (nea) specific radioactivity (> 2000 Ci/mmol) is described. In this approach, 2-(tributylstannyl)-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzyl alcohol 12 serves as a module which, through acylation of its alcohol function, is connected to other structural/functional elements to make the tin-containing precursor forms of the reagents. The final, radioactive compounds are then conveniently prepared in yields varying from 15-50% by electrophilic aromatic substitution of the tributylstannyl group by I-125(+) generated in situ from I-125(-) by peracetic acid. Using this approach, we have synthesized two analogues of phosphatidylcholine (PC) (20 and 21), an analogue of ceramide (36), as well as two heterobifunctional label-transfer cross-linkers (29 and 33). PC 21, examined more closely, is a substrate of the PC-specific phospholipid exchange protein from beef liver and of phospholipase D from cabbage. The latter was utilized to enzymatically convert PC 21 into two additional phospholipids, phosphatidylserine (PS) 25 and phosphatidic acid (PA) 26. Reagents that contain this iodinated photophor also combine desirable photochemical properties. Thus, evidence is presented that they undergo efficient photolysis to generate a (singlet) carbene intermediate which inserts efficiently into hydrocarbon CH bonds. In addition, we demonstrate that the diazirine can be photolyzed in a selective manner, that is, without photodeiodination to occur to a significant extent.
• Synthesis and Tritium Labeling of New Aromatic Diazirine Building Blocks for Photoaffinity Labeling and Cross-Linking
  作者：Yves Ambroise、Florence Pillon、Charles Mioskowski、Alain Valleix、Bernard Rousseau

  DOI：10.1002/1099-0690(200110)2001:20<3961::aid-ejoc3961>3.0.co;2-r

  日期：2001.10
• Consequences of Affinity in Heterogeneous Catalytic Reactions:  Highly Chemoselective Hydrogenolysis of Iodoarenes
  作者：Yves Ambroise、Charles Mioskowski、Gérald Djéga-Mariadassou、Bernard Rousseau

  DOI：10.1021/jo0012243

  日期：2000.10.1

  The catalytic hydrodeibdination reaction using molecular hydrogen and Pd/C has been revisited. It is shown, for the first time, that the chemoselectivity of this reaction is controlled by the high affinity of the iodinated compound for the catalyst. This reaction is compatible with most easily reducible functional groups (nitro, aldehyde, olefin, etc:). Using this reaction, the first general method for tritium labeling of 3-(triflubromethyl)-3-phenyldiazirine is described.
• Different chemical proteomic approaches to identify the targets of lapatinib
  作者：Tatjana Kovačević、Krunoslav Nujić、Mario Cindrić、Snježana Dragojević、Adrijana Vinter、Amela Hozić、Milan Mesić

  DOI：10.1080/14756366.2023.2183809

  日期：2023.12.31