9-(but-3-en-1-yl)-9H-carbazole | 10420-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-(but-3-en-1-yl)-9H-carbazole
• 英文别名: 9-but-3-enylcarbazole
• CAS: 10420-18-5
• 化学式: C₁₆H₁₅N
• 分子量: 221.302
• InChiKey: ZWLVPVOKFYNQHH-UHFFFAOYSA-N

物化性质

• 沸点：
  372.7±25.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-(but-3-en-1-yl)-9H-carbazole 在 potassium hydrogencarbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以22.6%的产率得到9-(2-(oxiran-2-yl)ethyl)-9H-carbazole
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies of 1,3-disubstituted 2-propanols as BACE-1 inhibitors

  摘要：

  A library of 1,3-disubstituted 2-propanols was synthesized and evaluated as low molecular weight probes for beta-secretase inhibition. By screening a library of 121 1,3-disubstituted 2-propanol derivatives, we identified few compounds inhibiting the enzyme at low micromolar concentrations. The initial hits were optimized to yield a potent BACE-1 inhibitor exhibiting an IC50 constant in the nanomolar range. Exploration of the pharmacological properties revealed that these small molecular inhibitors possessed a high selectivity over cathepsin D and desirable physicochemical properties beneficial to cross the blood-brain barrier. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.072
• 作为产物：
  描述：

  5-(carbazol-9-yl)-pent-1-yn-3-ol 在 lithium trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以87%的产率得到9-(but-3-en-1-yl)-9H-carbazole
  参考文献：
  名称：

  一种新的钌催化碳-碳三键断裂：乙炔醇有效转化为烯烃和一氧化碳

  摘要：

  我们报告了一种新的高效钌催化反应，可将乙炔醇转化为烯烃和一氧化碳。最有效的催化剂是 TpRu(PPh3)(CH3CN)2PF6 (10 mol%) 和三氟甲磺酸锂 (20 mol%)。使用同位素标记实验阐明了该反应的机制。

  DOI：

  10.1021/ja036246w

文献信息

• Visible‐Light‐Induced Three‐Component Intermolecular Trifluoromethyl‐Alkenylation Reactions of Unactivated Alkenes
  作者：Yuan‐Qiang Guo、Kaihua Wang、Ruiguo Wang、Hongjian Song、Yuxiu Liu、Qingmin Wang

  DOI：10.1002/adsc.202001434

  日期：2021.3.16

  visible‐light‐induced three‐component intermolecular trifluoromethyl‐alkenylation reactions of unactivated alkenes. The protocol has good functional group tolerance and a broad substrate scope. Using this protocol, we not only introduced a trifluoromethyl group into alkenes but also converted unactivated alkenes to styrene‐based activated alkenes, in addition to accomplishing late‐stage functionalization of pharmaceutical

  在此，我们描述了一种有效，温和，可见光诱导的未活化烯烃分子间三氟甲基-烯基化反应的实用方案。该协议具有良好的官能团耐受性和广泛的底物范围。使用该协议，我们不仅将三氟甲基引入烯烃中，而且还完成了医药中间体的后期功能化，还将未活化的烯烃转化为基于苯乙烯的活化烯烃。
• Gold‐Catalyzed 1,2‐Diarylation of Alkenes
  作者：Chetan C. Chintawar、Amit K. Yadav、Nitin T. Patil

  DOI：10.1002/anie.202002141

  日期：2020.7.13

  Herein, we disclose the gold‐catalyzed 1,2‐diarylation of alkenes through the interplay of ligand‐enabled AuI/AuIII catalysis with the idiosyncratic π‐activation mode of gold complexes. Unlike the classical migratory‐insertion‐based approach to 1,2‐diarylation, the present approach not only circumvents the formation of direct Ar−Ar′ coupling and Heck‐type side products but more intriguingly demonstrates

  本文中，我们通过配体使能的Au I / Au III催化与金配合物的特质π活化模式的相互作用揭示了金的烯烃1,2-二芳基化反应。与经典的基于迁移插入的方法进行1,2-二芳基化不同，本方法不仅规避了直接Ar-Ar'偶联和Heck型副产物的形成，而且更有趣地证明了其反应性和选择性与先前已知的互补金属催化（Pd，Ni或Cu）。对机理进行详细研究的结果表明，由于芳基烯烃具有非清白的性质，芳基碘化物向Au I络合物的氧化加成是限速步骤。
• Visible-light-induced thiotrifluoromethylation of terminal alkenes with sodium triflinate and benzenesulfonothioates
  作者：Weiguang Kong、Hejun An、Qiuling Song

  DOI：10.1039/c7cc03520a

  日期：——

  An unconventional reductive quenching cycle was developed to realize the visible-light-induced thiotrifluoromethylation of terminal alkenes. CF3SO2Na was used as an easy to handle CF3 radical source to afford the desired products in moderate to good yields. Mild reaction conditions and a broad substrate scope feature in this transformation.

  开发了非常规的还原淬灭循环以实现可见光诱导的末端烯烃的硫代三氟甲基化。CF 3 SO 2 Na用作易于处理的CF 3自由基源，以中等至良好的产率提供所需的产物。这种转化具有温和的反应条件和广泛的底物范围。
• An efficient regioselective hydrodifluoromethylation of unactivated alkenes with TMSCF₂CO₂Et at ambient temperature
  作者：Guobin Ma、Wen Wan、Jialiang Li、Qingyang Hu、Haizhen Jiang、Shizheng Zhu、Jing Wang、Jian Hao

  DOI：10.1039/c4cc04591b

  日期：——

  A mild, versatile and efficient method for the regioselective hydrodifluoromethylation of unactivated alkenes has been developed. This Ag-mediated Csp(3)-CF2 bond forming reaction provides easy access to a variety of vicinal alpha-difluoroacetate-containing alkanes.

  已经开发了温和，通用和有效的方法用于未活化烯烃的区域选择性加氢二氟甲基化。此银介导的Csp（3）-CF2键形成反应可轻松访问各种含邻位α-二氟乙酸酯的烷烃。
• Porphyrin compositions
  申请人：Litz Erik Kyle

  公开号：US20060152149A1

  公开（公告）日：2006-07-13

  Novel metal porphyrin compositions useful as organic phosphors are provided. The novel compositions are prepared from commercially available porphyrin-containing starting materials. In one instance a novel palladium-containing porphyrin composition having a number average molecular weight of greater than 12,000 grams per mole was prepared from 5,10,15,20-tetrakis(3′,5′-di(hydroxy)phenyl)-21H-23H-porphyrin by reaction first with palladium(II) acetylacetonate, followed by reaction with 2-bromo-2-methylpropionyl bromide, and subsequent group transfer reaction of the alpha-bromo ester groups with 9,9-dioctyl-2-vinylfluorene in the presence of CuBr as a radical initiator. The product polymer exhibited a number average molecular weight of 12,884 grams per mole, a weight average molecular weight of 14,338 grams per mole, and a robust red phosphorescent emission. Porphyrin containing copoylmers comprising structural units derived from 9,9-dioctyl-2-vinylfluorene and 9-anthracenylmethyl methacrylate were prepared in a similar fashion.

  提供用作有机荧光体的新型金属卟啉组合物。这些新型组合物是从商业可获得的含卟啉起始原料制备的。在一个实例中，通过首先与醋酸钯(II)反应，然后与2-溴-2-甲基丙酰溴反应，并在CuBr存在下将α-溴酯基团与9,9-二辛基-2-乙烯基芴进行基团转移反应，制备了一个平均分子量大于12,000克/摩尔的新型含钯卟啉组合物，起始原料为5,10,15,20-四(3′,5′-二(羟基)苯基)-21H-23H-卟啉。该产物聚合物的平均分子量为12,884克/摩尔，重均分子量为14,338克/摩尔，具有稳健的红色磷光发射。类似地制备了含卟啉的共聚物，其结构单元源自9,9-二辛基-2-乙烯基芴和9-蒽甲基丙烯酸甲酯。