2-(5-chloro-4-(methoxymethyl)-2,3-dihydro-1H-inden-1-yl)-1H-imidazole | 1092716-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(5-chloro-4-(methoxymethyl)-2,3-dihydro-1H-inden-1-yl)-1H-imidazole
• 英文别名: 2-[5-chloro-4-(methoxymethyl)-2,3-dihydro-1H-inden-1-yl]-1H-imidazole
• CAS: 1092716-66-9
• 化学式: C₁₄H₁₅ClN₂O
• 分子量: 262.739
• InChiKey: CMNAOKMSNCWOHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-chloro-4-(methoxymethyl)-2,3-dihydro-1H-inden-1-yl)-1H-imidazole 在 Chiracel OD-H column 作用下， 以 乙醇 、 正庚烷 、 二乙胺 为溶剂， 以57%的产率得到PF-3774076
  参考文献：
  名称：

  A concise synthesis of chiral indanes as α 1A adrenoceptor partial agonists

  摘要：

  The synthesis of a series of chiral indanes with reported am partial agonist activity is outlined, applying a rhodium catalysed cyclisation for template construction. This method was extended to the asymmetric synthesis of lead compound PF-03774076 (1) which was prepared on >20 g scale in seven steps. Highlights include Rh-mediated cyclocarbonylation and an asymmetric alkene hydrogenation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.004
• 作为产物：
  描述：

  2-氯-6-碘甲苯 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 正丁基锂 、 [(S)-2,2'-双(二苯基磷)-1,1'-联萘]二氯化钌(II) 、 氢气 、 三乙胺 、 三苯基膦 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醇 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， -78.0~160.0 ℃ 、6.89 MPa 条件下， 反应 52.5h， 生成 2-(5-chloro-4-(methoxymethyl)-2,3-dihydro-1H-inden-1-yl)-1H-imidazole
  参考文献：
  名称：

  A concise synthesis of chiral indanes as α 1A adrenoceptor partial agonists

  摘要：

  The synthesis of a series of chiral indanes with reported am partial agonist activity is outlined, applying a rhodium catalysed cyclisation for template construction. This method was extended to the asymmetric synthesis of lead compound PF-03774076 (1) which was prepared on >20 g scale in seven steps. Highlights include Rh-mediated cyclocarbonylation and an asymmetric alkene hydrogenation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.004

文献信息

• [18F]Difluorocarbene for positron emission tomography
  作者：Jeroen B. I. Sap、Claudio F. Meyer、Joseph Ford、Natan J. W. Straathof、Alexander B. Dürr、Mariah J. Lelos、Stephen J. Paisey、Tim A. Mollner、Sandrine M. Hell、Andrés A. Trabanco、Christophe Genicot、Christopher W. am Ende、Robert S. Paton、Matthew Tredwell、Véronique Gouverneur

  DOI：10.1038/s41586-022-04669-2

  日期：2022.6.2

  total-body Positron Emission Tomography (PET) has vastly broadened the range of research and clinical applications of this powerful molecular imaging technology1. Such possibilities have accelerated progress in 18F-radiochemistry with numerous methods available to 18F-label (hetero)arenes and alkanes2. However, access to 18F-difluoromethylated molecules in high molar activity (Am) is largely an unsolved problem

  全身正电子发射断层扫描 (PET) 的出现极大地拓宽了这种强大的分子成像技术的研究和临床应用范围1 。这种可能性加速了18 F-放射化学的进展，有多种方法可用于18 F-标记（杂）芳烃和烷烃2 。然而，尽管二氟甲基对于药物发现来说是不可或缺的，但获得高摩尔活性 (A m ) 的18 F-二氟甲基化分子很大程度上是一个未解决的问题3 。我们在此报告了一种通用解决方案，通过使用能够进行多种18 F-二氟甲基化过程的[ 18 F]二氟卡宾试剂将卡宾化学引入核成像领域。与数十种已知的二氟卡宾试剂相比，这种18 F 试剂经过精心设计，具有易于使用、高摩尔活性和多功能性。 Am的问题通过检查二氟碳烯前体电子变化时同位素稀释的可能性来解决。多种基于 [ 18 F]二氟卡宾的反应（包括 O-H、S-H 和 N-H 插入）以及利用普遍存在的官能团（如（硫代）酚、 N-杂芳烃和易于安装的芳基硼酸。通过高度复杂
• Novel 2-imidazoles as potent, selective and CNS penetrant α1A adrenoceptor partial agonists
  作者：Lee R. Roberts、Justin Bryans、Kelly Conlon、Gordon McMurray、Alan Stobie、Gavin A. Whitlock

  DOI：10.1016/j.bmcl.2008.10.066

  日期：2008.12

  A novel series of central nervous system (CNS) penetrant indane 2-imidazoles have been identified as potent, partial agonists of the alpha(1A) adrenergic receptor, having good selectivity over the alpha(1B), alpha(1D) and alpha(2) sub-types. A key structural motif to impart selectivity is a methylene spacer between the indane and a pendant substituent, which includes heterocycles, sulphones and ethers. Introduction of an ortho-halogen to this group led to a lowering of intrinsic efficacy (E-max). (C) 2008 Elsevier Ltd. All rights reserved.
• A concise synthesis of chiral indanes as α 1A adrenoceptor partial agonists
  作者：Lee R. Roberts、Matthew S. Corbett、Steven J. Fussell、Laure Hitzel、Alan S. Jessiman、Helen J. Mason、Rachel Osborne、Michael J. Ralph、Adam S.D. Stennett、Simon Wheeler、R. Ian Storer

  DOI：10.1016/j.tetlet.2015.10.004

  日期：2015.11

  The synthesis of a series of chiral indanes with reported am partial agonist activity is outlined, applying a rhodium catalysed cyclisation for template construction. This method was extended to the asymmetric synthesis of lead compound PF-03774076 (1) which was prepared on >20 g scale in seven steps. Highlights include Rh-mediated cyclocarbonylation and an asymmetric alkene hydrogenation. (C) 2015 Elsevier Ltd. All rights reserved.