1a,9b-dihydro-1-methylsulfonyl-1H-phenanthro<9,10-b>azirine | 81593-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1a,9b-dihydro-1-methylsulfonyl-1H-phenanthro<9,10-b>azirine
• 英文别名: 1a,9b-dihydro-1-(methanesulfonyl)-1H-phenanthro[9,10-b]azirine；N-methanesulfonylphenanthrene-9,10-imine；N-(Methylsulfonyl)phenanthrene 9,10-imine；1-methylsulfonyl-1a,9b-dihydrophenanthro[9,10-b]azirine
• CAS: 81593-11-5
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: OBWFTEYMWYDFEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1a,9b-dihydro-1-methylsulfonyl-1H-phenanthro<9,10-b>azirine 在 ammonium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 60.0h， 生成 trans-(9R,10R)-N⁶-[9,10-dihydro-10-(methanesulfonamido)phenanthren-9-yl]-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis of nucleoside adducts of highly mutagenic polycyclic aromatic imines

  摘要：

  Polycyclic arene imines are a class of highly potent mutagens that exhibit generally higher activity than the corresponding arene oxides. Efficient syntheses of adducts between a model polycyclic aromatic imine derivative of phenanthrene and the nucleosides adenosine, guanosine, cytidine, 2'-deoxyadenosine and 2'-deoxyguanosine are described. These compounds are needed as standards for identification of adducts formed by reaction of polycyclic arene imines with DNA in cells. (C) 1999 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00549-9
• 作为产物：
  描述：

  菲9,10-亚胺 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 1a,9b-dihydro-1-methylsulfonyl-1H-phenanthro<9,10-b>azirine
  参考文献：
  名称：

  Weitzberg, Moshe; Aizenshtat, Zeev; Blum, Jochanan, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1513 - 1516

  摘要：

  DOI：

文献信息

• Adducts of phenanthrene 9,10-imine and of benz[<i>a</i>]anthracene 5,6-imine to some nitrogen heterocycles
  作者：Yosef Shalom、Jochanan Blum、Ronald G. Harvey

  DOI：10.1002/jhet.5570330327

  日期：1996.5

  N-4-Pyridinyl-, N-2-quinolinyl-, and 2-pyrazinylphenanthrene 9,10-imines 4–6, as well as N-4-pyridinyl- and N-2-pyrazinylbenz[a]anthracene 5,6-imines 12 and 13 were prepared by sodium hydride-mediated interaction of the parent arene imines, 1 and 10, and the respective chloropyridine, chloroquinoline or chloropyrazine. N-Nicotynoyl-, N-2-pyridinoyl- and N-6-quinolinoylphenanthrene 9,10-imines 7–9 were

  Ñ -4-吡啶基，Ñ -2- quinolinyl-和2- pyrazinylphenanthrene -9,10-亚胺4-6，以及ñ -4-吡啶基和Ñ -2- pyrazinylbenz [一个]蒽5,6-通过氢化钠介导的母体芳烃亚胺1和10与各自的氯吡啶，氯喹啉或氯吡嗪的相互作用制备亚胺12和13。Ñ -Nicotynoyl-，Ñ -2- pyridinoyl-和Ñ -6- quinolinoylphenanthrene -9,10-亚胺7-9通过的相互作用获得Ñ-三甲基甲硅烷基菲9,10-亚胺（2）和合适的吡啶或喹啉羰基氯化物。的反应Ñ -methylsulfonylphenanthrene -9,10-亚胺与胸腺嘧啶，胞嘧啶，5-氟胞嘧啶，嘌呤，6-氯嘌呤和腺嘌呤，得到，在任一碳酸钾或1,5-二氮杂双环[3.4.0]壬-5-的存在烯，分别为加合物16-22。加合物的结构通过多核核磁
• WEITZBERG, M.;AIZENSHTAT, Z.;BLUM, J., J. HETEROCYCL. CHEM., 1981, 18, N 8, 1513-1516
  作者：WEITZBERG, M.、AIZENSHTAT, Z.、BLUM, J.

  DOI：——

  日期：——
• Synthesis of nucleoside adducts of highly mutagenic polycyclic aromatic imines
  作者：Yosef Shalom、Ronald G. Harvey、Jochanan Blum

  DOI：10.1016/s0040-4020(99)00549-9

  日期：1999.8

  Polycyclic arene imines are a class of highly potent mutagens that exhibit generally higher activity than the corresponding arene oxides. Efficient syntheses of adducts between a model polycyclic aromatic imine derivative of phenanthrene and the nucleosides adenosine, guanosine, cytidine, 2'-deoxyadenosine and 2'-deoxyguanosine are described. These compounds are needed as standards for identification of adducts formed by reaction of polycyclic arene imines with DNA in cells. (C) 1999 Elsevier Science Ltd, All rights reserved.
• Weitzberg, Moshe; Aizenshtat, Zeev; Blum, Jochanan, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1513 - 1516
  作者：Weitzberg, Moshe、Aizenshtat, Zeev、Blum, Jochanan

  DOI：——

  日期：——