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3-溴-3-(4-硝基苯基)-3H-双吖丙啶 | 115127-49-6

中文名称
3-溴-3-(4-硝基苯基)-3H-双吖丙啶
中文别名
——
英文名称
3-bromo-3-(4-nitrophenyl)diazirine
英文别名
3-bromo-3-p-nitrophenyldiazirine;(p-nitrophenyl)bromodiazirine;3-bromo-3-(4-nitro-phenyl)-diazirine;3-Bromo-3-(4-nitrophenyl)-3H-diazirine
3-溴-3-(4-硝基苯基)-3H-双吖丙啶化学式
CAS
115127-49-6
化学式
C7H4BrN3O2
mdl
——
分子量
242.032
InChiKey
UVRKMGKMERZZSY-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    33-35℃
  • 沸点:
    303.3±52.0 °C(Predicted)
  • 密度:
    2.00±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

  • 辛醇/水分配系数(LogP):
    2.5
  • 重原子数:
    13
  • 可旋转键数:
    1
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.14
  • 拓扑面积:
    70.5
  • 氢给体数:
    0
  • 氢受体数:
    4

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

点击查看最新优质反应信息

文献信息

  • A New Synthesis of Benzylidene Acetals
    作者:Chunbao Li、Andrea Vasella
    DOI:10.1002/hlca.19930760115
    日期:1993.2.10
    Aryl-halo-diazirines react under basic conditions with 1,3-cis-, 1,2-cisand 1,2-trans-diols to give acetals. Yields are high. Diastereoselectivities depend upon the diol and upon the reaction conditions. Thus, reaction of the 1,3-cis-diol 1 (Scheme 1) with 2 gave 3 as a single diastereoisomer. The 1,2-cis-diols 4 and 7 led to the endo- and exo-acetals 5/6 (93:7) and 8/9 (ca.10:1), respectively, The
    芳基卤代二嗪在碱性条件下与1,3-顺式,1,2-顺式和1,2-反式-二醇反应生成缩醛。产量高。非对映选择性取决于二醇和反应条件。因此,使1,3-顺-二醇1(方案1)与2反应,得到3为单一非对映异构体。1,2-顺式-diols 4和7导致内切-和外切-acetals 5 / 6(93:7)和8 / 9(CA0.10:1),分别为1,2-反式-diols 10,16,和19与反应2,得到11 / 12(90:10),17 / 18(1:1),和20 / 21( 6:1)。的(4-硝基苯基)二吖丙因的反应13与10在较高温度下,得到14 / 15(6:4)。尿嘧啶部分,乙酰胺基和烯醇醚部分与反应条件相容。根据涉及烷氧基-卤素交换的反应顺序合理化非对映选择性,该烷氧基-卤素交换具有或不具有区域选择性,随后的烷氧基二嗪热解,烷氧基卡宾的质子化以形成(E)-构型的氧羰基离子和相邻的氧基或羟基,仅对于有限范围的构象异构体是可能的。
  • Triplet halocarbene chemistry: p-nitrophenylchlorocarbene and p-nitrophenylbromocarbene
    作者:Robert A. Moss、Zhifeng Lu、Ronald R. Sauers
    DOI:10.1016/j.tetlet.2010.09.018
    日期:2010.11
    Reactions of p-nitrophenylchlorocarbene with cumene and of p-nitrophenylbromocarbene with toluene afford C–H abstraction–recombination products that suggest the involvement of triplet arylhalocarbenes.
    的反应p与枯烯和的-nitrophenylchlorocarbene p -nitrophenylbromocarbene用甲苯得到暗示三重arylhalocarbenes的参与C-H抽象重组产物。
  • Intramolecular Addition of Nucleophilic Carbenes to Acceptor-Substituted Alkenyl Groups: Synthesis and transformation of homobenzofurans and synthesis of a homoindole
    作者:Chunbao Li、Andrea Vasella
    DOI:10.1002/hlca.19930760114
    日期:1993.2.10
    The intramolecular addition of unsaturated alkoxycarbenes leads in high yields and diastereoselectively to fused cyclopropanes (Scheme 1). Reaction of the halodiazirines 2, 10, 11, and 20 with the unsaturated phenolates 1, 8, and 9 yielded intermediate alkoxydiazirines, and hence the homobenzofurans 5, 12–16, 22, and 26 (Scheme 2). The intermediate alkoxydiazirine 25 was isolated at low temperature
    分子内添加不饱和烷氧基卡宾导致高产率并且非对映选择性地产生稠合的环丙烷(方案1)。所述halodiazirines的反应2,10,11,和20与不饱和酚1,8,和9个得到中间alkoxydiazirines,因此homobenzofurans 5,12 - 16,22,和26(方案2)。在低温下分离出中间体烷氧基二嗪25(方案3)。环丙烷衍生物12和27以及14和28之间的平衡建立在120°。在200°,通过环丙烷环的旋旋打开,然后将其电环化,将12重排至色烯29。的氢化29,得到(清一色顺式) -苯并二氢吡喃32(方案4)。推测通过34和10的S RN 1反应以高收率获得均吲哚35(方案5)。
  • Spin selectivity in the oxygenation of singlet phenylhalocarbenes with oxygen
    作者:Taiki Makihara、Takayuki Nojima、Katsuya Ishiguro、Yasuhiko Sawaki
    DOI:10.1016/s0040-4039(02)02538-8
    日期:2003.1
    Singlet phenylhalocarbenes are shown to react with triplet oxygen and the apparent spin-forbidden oxygenation rates are strongly dependent on substituents, i.e. in the decreasing order of Br>Clmuch greater thanF for halogen and of p-NO2>Hmuch greater thanp-MeO for p-substituents. These results suggest the oxygenation of triplet halocarbene equilibrated with ground-state singlet, resulting in the first estimation of energy difference between the singlet and triplet states. (C) 2003 Elsevier Science Ltd. All rights reserved.
  • The invention of radical reactions. 30. Diazirines as carbon radical traps. Mechanistic aspects and synthetic applications of a novel and efficient amination process
    作者:Derek H. R. Barton、Joseph C. Jaszberenyi、Emmanouil A. Theodorakis、J. H. Reibenspies
    DOI:10.1021/ja00071a017
    日期:1993.9
    A number of diazirines were synthesized for the purpose of exploring the addition of a carbon radical to the nitrogen-nitrogen double bond. Carbon radicals, generated from the photolysis of the O-acyl derivatives of N-hydroxy-2-thiopyridone or via radical exchange from the corresponding organotellurides, were shown to add smoothly to the diazirines leading to imines 34. When 3-(trifluoromethyl)-3-phenyldiazirine (13) is used as the trap, the thus formed imines can be easily hydrolyzed to amines. A mechanism that involves dimerization of the diaziridinyl radicals 32 to produce tetraazo intermediates 33 is suggested in accord with variable temperature NMR data for the reaction. Proof for this mechanistic scheme was furthermore obtained by isolation and X-ray structure determination of 33d. The first X-ray structure of a 3-(trifluoromethyl)-3-aryldiazirine is also reported.
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