2-(1,3-benzodioxol-5-yl)-2-imidazoline | 70183-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(1,3-benzodioxol-5-yl)-2-imidazoline
• 英文别名: 2-(3,4-piperonyl)imidazoline；2-(1,3-benzodioxol-5-yl)-4,5-dihydro-1H-imidazole
• CAS: 70183-97-0
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: DINTYXOWAMJKHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  42.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对氯苯甲酸甲酯 、 2-(1,3-benzodioxol-5-yl)-2-imidazoline 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以15%的产率得到15-(4-Chlorophenyl)-3,5-dioxa-11,14-diazatetracyclo[7.6.0.0^{2,6}.0^{10,14}]pentadeca-1,6,8,10-tetraen-15-ol
  参考文献：
  名称：

  Mazindol Analogues as Potential Inhibitors of the Cocaine Binding Site at the Dopamine Transporter

  摘要：

  A series of mazindol. (2) and homomazindol (3) analogues with a variety of electron-donating and electron-withdrawing groups in the pendant aryl group and the benzo ring C, as well as H, methoxy, and alkyl groups replacing the hydroxyl group were synthesized, and their binding affinities at the dopamine transporter (DAT) on rat or guinea pig striatal. membranes were determined. Several active analogues were also evaluated for their ability to block uptake of DA, 5-HT, and NE and inhibit binding of [I-125] RTI-55 at HEK-hDAT, HEK-hSERT, and HEK-hNET cells. Mazindane (26) was found to be a pro-drug, oxidizing (5-H --> 5-OH) to mazindol on rat striatal membranes and HEk-hDAT cells. The 4',7,8-trichloro analogue (38) of mazindol was the I most potent and selective ligand. for HEK-hDAT cells (DAT K-i = 1.1 nM; SERT/DAT 1283 and NET/DAT = 38). Experimental results strongly favor the cyclic or ol tautomers of 2 and 3 to bind more, tightly at the DAT than the corresponding keto tautomers.

  DOI：

  10.1021/jm010302r
• 作为产物：
  描述：

  乙二胺 、 2-Benzo[1,3]dioxol-5-yl-3,4,4-trimethyl-4,5-dihydro-oxazol-3-ium; iodide 以 乙腈 为溶剂， 反应 10.0h， 以61%的产率得到2-(1,3-benzodioxol-5-yl)-2-imidazoline
  参考文献：
  名称：

  Mazindol Analogues as Potential Inhibitors of the Cocaine Binding Site at the Dopamine Transporter

  摘要：

  A series of mazindol. (2) and homomazindol (3) analogues with a variety of electron-donating and electron-withdrawing groups in the pendant aryl group and the benzo ring C, as well as H, methoxy, and alkyl groups replacing the hydroxyl group were synthesized, and their binding affinities at the dopamine transporter (DAT) on rat or guinea pig striatal. membranes were determined. Several active analogues were also evaluated for their ability to block uptake of DA, 5-HT, and NE and inhibit binding of [I-125] RTI-55 at HEK-hDAT, HEK-hSERT, and HEK-hNET cells. Mazindane (26) was found to be a pro-drug, oxidizing (5-H --> 5-OH) to mazindol on rat striatal membranes and HEk-hDAT cells. The 4',7,8-trichloro analogue (38) of mazindol was the I most potent and selective ligand. for HEK-hDAT cells (DAT K-i = 1.1 nM; SERT/DAT 1283 and NET/DAT = 38). Experimental results strongly favor the cyclic or ol tautomers of 2 and 3 to bind more, tightly at the DAT than the corresponding keto tautomers.

  DOI：

  10.1021/jm010302r

文献信息

• Synthesis and pharmacological evaluation of imidazoline sites I1 and I2 selective ligands
  作者：Maria Anastassiadou、Saı̈da Danoun、Louis Crane、Geneviève Baziard-Mouysset、Marc Payard、Daniel-Henri Caignard、Marie-Claire Rettori、Pierre Renard

  DOI：10.1016/s0968-0896(00)00280-7

  日期：2001.3

  heterocyclic-imidazoline compounds have been prepared and evaluated in vitro as imidazoline sites (I1 and I2) and alpha-adrenergic (alpha1 and alpha2) receptor ligands. Their pKi values indicate that linkage of the imidazoline moiety at the 2-position with an aromatic substituent dramatically decreases alpha-adrenergic affinity. I1 sites are more accessible by phenyl imidazolines substituted by a methyl or a methoxy

  已经制备了几种系列的2-芳基或杂环-咪唑啉化合物，并在体外评估为咪唑啉位点（I1和I2）和α-肾上腺素能（α1和α2）受体配体。它们的pKi值表明2-位咪唑啉部分与芳族取代基的连接显着降低了α-肾上腺素的亲和力。通过在邻位或间位上被甲基或甲氧基取代的苯基咪唑啉更易于接近I1位点。实际上，2-（2'-甲氧基苯基）-咪唑啉（17）是有史以来最好的I1配体之一（pKi = 8.53，I1 / I2> 3388）。另一方面，在对位中存在甲基时，I 2选择性增加。原始化合物2-（3'-氟-4'-甲苯基）-咪唑啉（31）是I2位点的新有效配体，具有高选择性（pKi = 8。
• Efficient Synthesis of 2-Imidazolines in the Presence of Molecular Iodine Under Ultrasound Irradiation
  作者：Guo-Feng Chen、Hong-Yang Li、Nan Xiao、Bao-Hua Chen、Ya-Li Song、Ji-Tai Li、Zhi-Wei Li

  DOI：10.1071/ch13700

  日期：——

  An efficient one-pot synthesis process for preparing 2-imidazolines from aldehydes and ethylenediamine using molecular iodine and potassium carbonate in absolute ethanol at 25–30°C under ultrasound irradiation is described. The synthetic strategy has the following advantages: mild conditions and low costs requirements, readily available catalyst, short reaction times, simplicity of operation, and good-to-excellent yields.

  本研究介绍了一种高效的单锅合成工艺，该工艺在 25-30°C 超声波照射下，使用分子碘和碳酸钾在绝对乙醇中以醛和乙二胺为原料制备 2-咪唑啉。该合成策略具有以下优点：条件温和、成本要求低、催化剂容易获得、反应时间短、操作简单以及良好的收率。
• Long-range metal–ligand bifunctional catalysis: cyclometallated iridium catalysts for the mild and rapid dehydrogenation of formic acid
  作者：Jonathan H. Barnard、Chao Wang、Neil G. Berry、Jianliang Xiao

  DOI：10.1039/c2sc21923a

  日期：——

  Formic acid (HCO2H) is an important potential hydrogen storage material, which, in the presence of appropriate catalysts can be selectively dehydrogenated to give H2 and CO2. In this work, well defined N^C cyclometallated iridium(III) complexes based on 2-aryl imidazoline ligands are found to be excellent catalysts for the decomposition of HCO2H–NEt3 mixtures to give H2 and CO2 under mild conditions with high turnover frequencies (up to 147 000 h−1 at 40 °C) and essentially no CO formation. The modular structures of these catalysts have allowed for the construction of structure–activity relationships for the complexes, leading to the rational optimisation of the catalyst structure with respect to both the rate of H2 production and catalyst lifetime. In particular, the presence of the remote γ-NH unit in the ligand is shown to be essential for catalytic activity, without which no reaction occurs. Mechanistic studies suggest that the dehydrogenation is rate-limited by the step of hydride protonation, which is made feasible by the γ-NH unit via an unusual form of long-range metal–ligand bifunctional catalysis involving formic acid-assisted proton hopping.

  甲酸 (HCO2H) 是一种重要的潜在氢储存材料，在适当的催化剂存在下，可以选择性地脱氢生成氢气 (H2) 和二氧化碳 (CO2)。本研究发现，基于 2-芳基咪唑啉配体的明确 N^C 环金属化铱(III) 配合物是 HCO2H–NEt3 混合物分解的优良催化剂，在温和条件下以高周转频率（在 40°C 下可达 147,000 h–1）产生 H2 和 CO2，并几乎没有 CO 的生成。这些催化剂的模块化结构使得能够建立配合物的结构–活性关系，从而合理优化催化剂结构以提高 H2 生产速率和催化剂寿命。特别是，配体中远程的 γ-NH 单元被证明对催化活性至关重要，没有该单元时不发生反应。机理研究表明，脱氢反应的速率受限于氢化物质子化步骤，而这一过程通过 γ-NH 单元以一种不寻常的长程金属–配体双功能催化形式实现，这涉及到甲酸辅助的质子跃迁。
• A Facile and Efficient Synthesis of 2-Imidazolines from Aldehydes Using Hydrogen Peroxide and Substoichiometric Sodium Iodide
  作者：Guo-yi Bai、Kai Xu、Guo-feng Chen、Yong-hui Yang、Tian-yu Li

  DOI：10.1055/s-0030-1259992

  日期：2011.5

  The reaction of aldehydes with ethylenediamine for the preparation of 2-imidazolines has been studied using hydrogen peroxide as an oxidant in the presence of sodium iodide and anhydrous magnesium sulfate. A mild, green, and efficient method is established to carry out this reaction in high yield. 2-imidazoline - hydrogen peroxide - aldehydes - ethylenediamine - environmentally friendly process

  在碘化钠和无水硫酸镁存在下，使用过氧化氢作为氧化剂，已经研究了醛与乙二胺反应制备2-咪唑啉的反应。建立了温和，绿色和有效的方法以高产率进行该反应。 2-咪唑啉-过氧化氢-醛-乙二胺-环保工艺
• Mazindol Analogues as Potential Inhibitors of the Cocaine Binding Site at the Dopamine Transporter
  作者：William J. Houlihan、Lawrence Kelly、Jessica Pankuch、Judith Koletar、Leonard Brand、Aaron Janowsky、Theresa A. Kopajtic

  DOI：10.1021/jm010302r

  日期：2002.9.1

  A series of mazindol. (2) and homomazindol (3) analogues with a variety of electron-donating and electron-withdrawing groups in the pendant aryl group and the benzo ring C, as well as H, methoxy, and alkyl groups replacing the hydroxyl group were synthesized, and their binding affinities at the dopamine transporter (DAT) on rat or guinea pig striatal. membranes were determined. Several active analogues were also evaluated for their ability to block uptake of DA, 5-HT, and NE and inhibit binding of [I-125] RTI-55 at HEK-hDAT, HEK-hSERT, and HEK-hNET cells. Mazindane (26) was found to be a pro-drug, oxidizing (5-H --> 5-OH) to mazindol on rat striatal membranes and HEk-hDAT cells. The 4',7,8-trichloro analogue (38) of mazindol was the I most potent and selective ligand. for HEK-hDAT cells (DAT K-i = 1.1 nM; SERT/DAT 1283 and NET/DAT = 38). Experimental results strongly favor the cyclic or ol tautomers of 2 and 3 to bind more, tightly at the DAT than the corresponding keto tautomers.