3-(5-(bromomethyl)-3-iodo-phenyl)-3-trifluoromethyl-3H-diazirine | 309250-32-6

• 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: 3-(5-(bromomethyl)-3-iodo-phenyl)-3-trifluoromethyl-3H-diazirine
• 英文别名: 3-[3-(Bromomethyl)-5-iodophenyl]-3-(trifluoromethyl)-3H-diazirine；3-[3-(bromomethyl)-5-iodophenyl]-3-(trifluoromethyl)diazirine
• CAS: 309250-32-6
• 化学式: C₉H₅BrF₃IN₂
• 分子量: 404.956
• InChiKey: GUWZVTKXIFXHOQ-UHFFFAOYSA-N

物化性质

• 密度：
  2.25±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：
  24.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(5-(bromomethyl)-3-iodo-phenyl)-3-trifluoromethyl-3H-diazirine 在 六甲基磷酰三胺 、 正丁基锂 、 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  A novel photoaffinity probe for the LTD4 receptor

  摘要：

  A novel photoaffinity probe for the leukotriene D-4 receptor (LTD4) is described. L-745310, which is structurally related to the potent LTD4 antagonist MK-0476 (Singulair(TM)), was found to selectively label a 43-kDa protein in guinea-pig lung membrane previously identified as the LTD4 receptor. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10011-6
• 作为产物：
  描述：

  3-[3-(tert-Butyl-dimethyl-silanyloxymethyl)-5-iodo-phenyl]-3-trifluoromethyl-3H-diazirine 在 四溴化碳 、 双硫磷 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 3-(5-(bromomethyl)-3-iodo-phenyl)-3-trifluoromethyl-3H-diazirine
  参考文献：
  名称：

  A novel photoaffinity probe for the LTD4 receptor

  摘要：

  A novel photoaffinity probe for the leukotriene D-4 receptor (LTD4) is described. L-745310, which is structurally related to the potent LTD4 antagonist MK-0476 (Singulair(TM)), was found to selectively label a 43-kDa protein in guinea-pig lung membrane previously identified as the LTD4 receptor. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10011-6

文献信息

• Hunting the Emesis and Efficacy Targets of PDE4 Inhibitors:  Identification of the Photoaffinity Probe 8-(3-Azidophenyl)-6- [(4-iodo-1<i>H</i>-1-imidazolyl)methyl]quinoline (APIIMQ)
  作者：Dwight Macdonald、Hélène Perrier、Susana Liu、France Laliberté,、Roberta Rasori、Annette Robichaud、Paul Masson、Zheng Huang

  DOI：10.1021/jm000065c

  日期：2000.10.1
• [125I]-N-[(3-Azido-5-iodo)benzyl]dantrolene and [125I]-N-{[3-Iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl)]benzyl}dantrolene: photoaffinity probes specific for the physiological Ca2+ release from sarcoplasmic reticulum of skeletal muscle
  作者：Takamitsu Hosoya、Hiroshi Aoyama、Takaaki Ikemoto、Toshiyuki Hiramatsu、Yasutaka Kihara、Makoto Endo、Masaaki Suzuki

  DOI：10.1016/s0960-894x(02)00701-1

  日期：2002.11

  In order to capture and identify key molecules that regulate the release of Ca2+ from the sarcoplasmic reticulum (SR) of skeletal muscle, we designed specific photoaffinity probes based on the structural modification of dantrolene. Thus, GIF-0082 and GIF-0276 possessing azido- and trifluoromethyldiazirinyl-benzyl groups, respectively, at the hydantoin moiety were found to have a highly selective inhibitory effect on physiological Ca2+ release (PCR) without affecting Ca2+-induced Ca2+ release (CICR). Successful realization of the sharp discrimination between PCR and CICR has led to the creation of [I-125]GIF-0082 and [I-125]GIF-0276, which were synthesized by substituting a stannyl group with I-125 in the corresponding phenylstannane precursors. (C) 2002 Published by Elsevier Science Ltd.