1-丙基-(9ci)-1H-苯并咪唑 | 7665-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-丙基-(9ci)-1H-苯并咪唑
• 英文名称: 1-propylbenzimidazole
• 英文别名: N-propylbenzimidazole；1-n-propylbenzimidazole；1-Propyl-benzimidazol；N-n-propylbenzimidazole；1-propyl-1H-benzimidazole
• CAS: 7665-66-9
• 化学式: C₁₀H₁₂N₂
• mdl: MFCD00704058
• 分子量: 160.219
• InChiKey: LZUVIELFLONRSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-丙基-(9ci)-1H-苯并咪唑 在 tetrafluoroboric acid 作用下， 以 乙醇 为溶剂， 以98%的产率得到1-propylbenzimidazolium tetrafluoroborate
  参考文献：
  名称：

  Preparation and Characterization of Two Brønsted Acid Ionic Liquids

  摘要：

  合成并表征了两种基于苯并咪唑阳离子的布伦特酸任务特定离子液体（1-乙基苯并咪唑四氟硼酸盐{[H-eBim]BF4 (1)}和 1-丙基苯并咪唑四氟硼酸盐{[H-pBim]BF4 (2)}）。1 的晶体为正方晶系，空间群为 Pnma，单胞参数如下：a = 9.9308(16), b = 6.8813(11), c = 15.345(3) Å, V = 1048.6(3) Å3, Z = 4, Dc = 1.482 g/cm3.结构 2 在单斜空间群 P21/c 中结晶，单胞 a = 4.9688(14), b = 13.684(4), c = 17.295(5) Å, β = 92.090(6)°, V = 1175.2(6) Å3, Z = 4, Dc = 1.402 g/cm3.这些分子在固态下通过分子内和分子间的各种氢键相互作用而稳定下来，形成聚合物结构。我们合成了两种基于苯并咪唑阳离子的布氏酸任务特异性离子液体，并对其进行了表征。

  DOI：

  10.1007/s10870-011-0038-2
• 作为产物：
  描述：

  (9ci)-1-(3-氯丙基)-1H-苯并咪唑 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 9.17h， 生成 1-丙基-(9ci)-1H-苯并咪唑
  参考文献：
  名称：

  Radical cyclisation onto imidazoles and benzimidazoles

  摘要：

  New synthetic methodology has been developed for the synthesis of [1,2-a]Fused imidazoles and benzimidazoles using intramolecular homolytic aromatic substitution. In the intramolecular substitution, N-(omega-alkyl) radicals are generated using Bu3SnH from N-(omega-phenylselanyl)aIkyl side chains. Phenylselanyl groups are used as radical leaving groups to avoid problems in the N-alkylation of imidazoles and benzimidazoles. Arylsulfones for imidazoles, and phenylsulfides for benzimidazoles, are used as the leaving groups in the homolytic substitutions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00104-0

文献信息

• Barton esters for initiator-free radical cyclisation with heteroaromatic substitution
  作者：Robert Coyle、Karen Fahey、Fawaz Aldabbagh

  DOI：10.1039/c3ob27313j

  日期：——

  first examples of efficient radical cyclisation with (hetero)aromatic substitution via Barton ester intermediates. Cyclopropyl and alkyl radicals allow access to five, six and seven-membered alicyclic-ring fused heterocycles with and without an additional fused cyclopropane, including the skeleton of the anti-cancer agent, cyclopropamitosene, expanded, and diazole analogues. Radical initiators are not

  S-（1-Oxido-2-pyridinyl）-1,1,3,3-tetramethylthiouronium hexafluorophosphate（HOTT）促进了通过Barton酯中间体进行（杂）芳香取代的有效自由基环化的第一个例子。环丙基和烷基可与五个，六个和七元脂环族稠合杂环一起使用，无论是否有其他稠合环丙烷，包括抗癌药环丙烷酰胺的骨架，展开的和 二唑类似物。自由基引发剂是不需要用于从羧酸前体的环化。
• [EN] ALPHA-AMINO BORONIC ACID DERIVATIVES, SELECTIVE IMMUNOPROTEASOME INHIBITORS<br/>[FR] DÉRIVÉS D'ACIDE ALPHA-AMINO BORONIQUE, INHIBITEURS SÉLECTIFS DE L'IMMUNOPROTÉASOME
  申请人：ARES TRADING SA

  公开号：WO2013092979A1

  公开（公告）日：2013-06-27

  The present invention provides compounds of Formula (I) as inhibitors of LMP7 for the treatment of autoimmune and inflammatory diseases. In formula (I), Rb and Rc are independently selected from one another from H or C1-C6-alkyl; whereby Rb and Rc may be linked to form a 5 or 6 membered-ring containing the oxygen atoms to which they are linked; Q denotes Ar, Het or cycloalkyl; R1 R2 independently from each other denotes H, ORa, Hal, C1-C6-alkyl wherein 1 to 5 H atoms may be independently replaced by OH or Hal; Y denotes CR 3R4, preferably CH2 or C(CH3)2; R 3, R4 independently of one another denote H or C1-C6-alkyl; L denotes L1 or L2 or alkyl; n is an integer selected from 0 to 3; L 1 is Q1-CO-M- wherein Q 1 is Ar or Het, preferably, phenyl, naphthyl or pyridine, optionally substituted with 1 to 5 groups independently selected from ORa, Hal, phenyl, and C1-C6-alkyl wherein 1 to 5 H atoms may be independently replaced by OH or Hal; L2 is Q2-M- wherein Q 2 is a fused bicyclic system containing 1 nitrogen atom and 1 to 3 additional groups independently selected from O, S, N, or CO, and wherein at least one of the rings is aromatic whereby the fused bicyclic system is optionally substituted with 1 to 5 groups independently selected from ORa, Hal, phenyl, and C1-C6-alkyl wherein 1 to 5 H atoms may be independently replaced by OH or Hal; or Q 2 is unsaturated or aromatic 5 membered-ring system containing 1 to 3 heteroatoms selected from N, O, S and CO, and optionally substituted with a phenyl ring or pyridine ring whereby phenyl ring and pyridine ring are optionally substituted with 1 to 4 groups independently selected from ORa, Hal, phenyl, and C1-C6-alkyl wherein 1 to 5 H atoms may be independently replaced by OH or Hal; M is a linear or branched alkylene having 1 to 5 carbon atoms wherein 1 or 2 H atoms may be replaced by OR a or a phenyl ring optionally substituted with 1 to 5 groups independently selected from Hal, ORa, and C1-C6-alkyl optionally substituted with 1 to 5 groups independently selected from OH, and Hal; or M denotes a cycloalkylene having 3 to 7 carbon atoms; or M denotes a thiazolidinyl group; R a is H or C1-C6-alkyl wherein 1 to 5 H atom may be independently replaced by OH or Hal; Ar denotes a 6 membered-aromatic carbocyclic ring optionally fused with another carbocyclic saturated, unsaturated or aromatic ring having 5 to 8 carbon atoms; Het denotes a 5- or 6-membered saturated, unsaturated or aromatic heterocyclic ring having 1 to 3 heteroatoms independently selected from N, N+O-, O, S, SO, and SO 2, and optionally fused with another saturated, unsaturated or aromatic ring having 5 to 8 atoms and optionally containing 1 to 3 heteroatoms selected from N, O, and S; Hal denotes CI, Br, I of F; preferably CI or F.

  本发明提供了化合物的公式（I）作为LMP7的抑制剂，用于治疗自身免疫和炎症性疾病。在公式（I）中，Rb和Rc分别独立地从H或C1-C6-烷基中选择；其中Rb和Rc可以连接形成一个含有它们连接的氧原子的5或6元环；Q表示Ar，Het或环烷基；R1和R2彼此独立地表示H，ORa，Hal，C1-C6-烷基，其中1到5个H原子可以独立地被OH或Hal替换；Y表示CR 3R4，优选CH2或C(CH3)2；R3，R4彼此独立地表示H或C1-C6-烷基；L表示L1或L2或烷基；n是从0到3选择的整数；L1是Q1-CO-M-，其中Q1是Ar或Het，优选苯基，萘基或吡啶基，可选地取代为1到5个从ORa，Hal，苯基和C1-C6-烷基中独立选择的基团，其中1到5个H原子可以独立地被OH或Hal替换；L2是Q2-M-，其中Q2是含有1个氮原子和1到3个额外基团的融合双环系统，独立选择自O，S，N或CO，其中至少一个环是芳香环，融合双环系统可选地取代为1到5个从ORa，Hal，苯基和C1-C6-烷基中独立选择的基团，其中1到5个H原子可以独立地被OH或Hal替换；或Q2是不饱和或芳香的含有1到3个从N，O，S和CO中选择的杂原子的5元环系统，并可选地取代为苯环或吡啶环，其中苯环和吡啶环可选地取代为1到4个从ORa，Hal，苯基和C1-C6-烷基中独立选择的基团，其中1到5个H原子可以独立地被OH或Hal替换；M是具有1到5个碳原子的线性或支链烷基，其中1或2个H原子可以被ORa或可选地取代为1到5个从Hal，ORa和C1-C6-烷基中独立选择的基团，可选地取代为1到5个从OH和Hal中独立选择的基团；或M表示具有3到7个碳原子的环烷基；或M表示噻唑烷基；Ra是H或C1-C6-烷基，其中1到5个H原子可以独立地被OH或Hal替换；Ar表示一个6元芳香碳环，可选地与另一个含有5到8个碳原子的碳环饱和、不饱和或芳香环融合；Het表示一个含有1到3个从N，N+O-，O，S，SO和SO2中独立选择的杂原子的5或6元饱和、不饱和或芳香杂环，可选地与另一个含有5到8个原子的饱和、不饱和或芳香环融合，并可选地含有1到3个从N，O和S中选择的杂原子；Hal表示CI，Br，I或F；优选CI或F。
• Structures of NHC Hg(<scp>ii</scp>) and Ag(<scp>i</scp>) complexes and selective recognition of nitrate anion
  作者：Qing-Xiang Liu、Zhi-Xiang Zhao、Xiao-Jun Zhao、Qing Wei、Ai-Hui Chen、Hui-Long Li、Xiu-Guang Wang

  DOI：10.1039/c4ce01519c

  日期：——

  atoms in dilute solution. For the open structure of complexes 5 and 8, 5 contains an anionic unit [Hg3Cl8]2−, and 8 is formed as a dimer through two [L3Ag2Cl2] monomers. The study of selective recognition of anions on the basis of fluorescence and UV/vis spectroscopic titrations indicates that macrometallocycle 6 is an effective chemosensor for nitrate anion.

  已合成和表征了一系列双苯并咪唑鎓盐（或双咪唑鎓盐）及其八种N-杂环卡宾汞（II）和银（I）配合物（1-8）。配合物1-4和6包含通过一个双齿卡宾配体和一个金属离子形成的相似的大金属环。它们的主要区别在于它们的阴离子单元，这与添加的金属来源的数量有关。在络合物7中，稀溶液中通过两个配体和两个银（I）原子生成一个30元的大金属环。对于复合物5和8的开放结构，5包含阴离子单元[Hg 3 Cl 8 ] 2-，并且8通过两个[L 3 Ag 2 Cl 2 ]单体形成为二聚体。基于荧光和紫外/可见光谱滴定法选择性识别阴离子的研究表明，大金属环6是硝酸根阴离子的有效化学传感器。
• Silver(I), palladium(II) and mercury(II) NHC complexes based on bis-benzimidazole salts with mesitylene linker: Synthesis, structural studies and catalytic activity
  作者：Qing-Xiang Liu、Li-Xuan Zhao、Xiao-Jun Zhao、Zhi-Xiang Zhao、Zhi-Qiang Wang、Ai-Hui Chen、Xiu-Guang Wang

  DOI：10.1016/j.jorganchem.2013.01.026

  日期：2013.5

  by two precursor 1 and two silver(I) atoms are connected together via Ag2Br4 unit to form a 1D polymeric chain. Complex 7 adopted an open structure formed by one precursor 1 and two Pd(II) atoms. In complex 8, a bidentate dicarbene from precursor 2 and a doubly deprotonated acetonitrile coordinate with two Hg(II) atoms to afford a funnel-like structure. The 10-membered macrometallocycle of 9 was formed

  所述diimidazolium盐双[1-R-imidazoliumylmethyl]均三甲苯·2X（1：R =的PhCH 2，X  = Br的-和2：R =的Et，X  = PF 6 -）和dibenzimidazolium盐双[1-R-benzimidazoliumylmethyl ]均三甲苯·2X（3：R =  ñ PR，X  = I - ; 4：R =的PhCH 2，X  = I - ），以及它们的4 NHC银（I），钯（II），汞（II）络合物，[1,3,5-三甲基（CH 2 imyPhCH 2）2 ] 2Ag 2 ·Ag 2 Br 4 } n（6），间苯三甲[[CH 2 imyPhCH 2）PdCl 2（CH 3 CN）] 2 }（7），间苯三甲[[CH 2 imyEt）2 Hg 2（CHCN） ] [HgI 4 ]}（8）和[1,3,5-三甲基（CH 2 bimy n Pr）2
• <i>In-situ</i> approach for the synthesis of bromide-bridged mercury(II) <i>N</i>-heterocyclic carbene complexes
  作者：Muhammad Atif、Haq Nawaz Bhatti、Muhammad Adnan Iqbal、Yasir Jamil

  DOI：10.1080/00958972.2020.1765337

  日期：2020.4.17

  bromide-bridged mercury(II) symmetric and non-symmetric N-heterocyclic carbene complexes. The preparation of benzimidazolium salts (4–6) was accomplished by symmetrical and non-symmetrical substitution on benzimidazole. The salts were subjected to an in-situ process for metallation to get [Hg(II)-NHC] complexes [(HgBr-NHC)(µ2Br)2] (7–9) by reacting benzimidazolium salts (4–6) with mercury(II) acetate at

  摘要 本研究旨在合成溴桥汞(II) 对称和非对称N-杂环卡宾配合物。苯并咪唑鎓盐（4-6）的制备是通过苯并咪唑上的对称和非对称取代来完成的。通过使苯并咪唑鎓盐 (4-6) 与汞反应，对盐进行原位金属化过程以得到 [Hg(II)-NHC] 配合物 [(HgBr-NHC)(µ2Br)2] (7-9) (II) 室温下的醋酸盐。通过元素分析、FT-IR和NMR光谱表征化合物。7 和 8 的单晶通过 X 射线晶体学技术分析，显示出具有两个桥接溴化物的四面体双核配合物。还通过在惰性气氛下使 7-9 与镱粉反应来探索氧化还原金属转移法 (RTM) 合成镱配合物的可行性。产品是金属汞、苯并咪唑鎓盐和溴化镱而不是镱配合物。图形概要