1-allyl-1H-pyrrolo[2,3-b]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 1-allyl-1H-pyrrolo[2,3-b]pyridine
• 英文别名: 1-Prop-2-enylpyrrolo[2,3-b]pyridine
• 化学式: C₁₀H₁₀N₂
• 分子量: 158.203
• InChiKey: UDVAXGHTTKDIDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-allyl-1H-pyrrolo[2,3-b]pyridine 在 manganese(IV) oxide 、 溶剂黄146 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 1-(2-丙烯-1-基)-1H-吡咯并[2,3-B]吡啶-3-羧酸甲酯
  参考文献：
  名称：

  新的5-HT3（5-羟色胺3）受体拮抗剂。IV。氮杂双环烷乙酰胺衍生物的合成及其构效关系。

  摘要：

  描述了一系列新型的氮杂双环烷作为5-HT3（5-羟色胺-3）受体拮抗剂的合成与构效关系。我们对氮杂双环烷乙酰胺衍生物的研究表明，由2，3-二氢吲哚作为芳香环部分提供了有效的5-HT3受体拮抗剂活性，这是通过在麻醉的大鼠中静脉注射2-甲基5-羟色胺诱导的心动过缓而判断的。7-氮杂吲哚作为芳族部分提供弱的5-HT 3受体拮抗剂活性。这项研究中最好的5-HT3拮抗剂是3,3-二乙基-（9k）和3,3-二甲基-2,3-二氢-1-[[（8-甲基-8-氮杂双环）[3.2.1]]。辛基-3-羟基）乙酰基1H-吲哚（9d），其效力比恩丹西酮（1）高约10倍。

  DOI：

  10.1248/cpb.43.1351
• 作为产物：
  描述：

  7-氮杂吲哚 、 烯丙醇 在 1,1'-双(二苯基膦)二茂铁 、 bis(1,5-cyclooctadiene)nickel (0) 作用下， 以 二甲基亚砜 为溶剂， 反应 17.0h， 以60%的产率得到1-allyl-1H-pyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  The Selective Nickel‐Catalyzed N ‐Allylation of C3‐Unprotected Indoles under Mild and Clean Conditions

  摘要：

  AbstractA simple salt free and selective N‐allylation of indoles with allylic alcohols has been developed. The protocol uses a catalytic amount of a nickel complex generated in situ from Ni(cod)2 and dppf as diphosphine. The use of DMSO as the reaction solvent is crucial to control the regioselectivity of the reaction with the exclusive formation of the N‐allyl product among up to three possible products.

  DOI：

  10.1002/ejoc.202200042

文献信息

• <i>B</i>-Alkyl sp³–sp² Suzuki–Miyaura Couplings under Mild Aqueous Micellar Conditions
  作者：Nicholas R. Lee、Roscoe T. H. Linstadt、Danielle J. Gloisten、Fabrice Gallou、Bruce H. Lipshutz

  DOI：10.1021/acs.orglett.8b00961

  日期：2018.5.18

  B-sp3-alkyl reagents for Suzuki–Miyaura couplings under aqueous micellar catalysis conditions is reported. Studies as to substrate scope, use in a four-step one-pot sequence, and reaction medium recycling exemplify the synthetic utility of this technology. OBBD (B-alkyl-9-oxa-10-borabicyclo[3.3.2]decane) derivatives are easily made and utilized for couplings under mild conditions. Comparisons were also

  据报道，在水胶束催化条件下，将B -sp 3-烷基试剂用于Suzuki-Miyaura偶联。关于底物范围的研究，在四步一锅法中的使用以及反应介质的循环利用，例证了该技术的合成效用。OBBD（B-烷基-9-氧杂-10-borabicyclo [3.3.2]癸烷）衍生物很容易制备，并用于温和条件下的偶联。还比较了OBBD和作为反应伙伴的9-BBN（B-烷基-9-硼环[3.3.1]壬烷）衍生物。
• 7-azaindirubins, 7'-azaindirubins, 7-7'-diazaindirubin and the corresponding 3'-oxime ether derivates: production thereof, their production and use as a medicament
  申请人：Technische Universität Kaiserslautern

  公开号：EP2199292A1

  公开（公告）日：2010-06-23

  The present invention relates to 7-azaindirubins (1), 7'-azaindirubins (2), and 7,7'-diaza-indirubins (3), wherein E, R1 and R2 have the meanings detailed in the description, their production and use as a medicament for treating cancer, neurodegenerative diseases, bipolar disorders, inflammatory and infectious diseases, including viral diseases. Depending on structure, these indirubins act as inhibitors of various kinases involved in tumor cell growth, and, most notably, as inhibitors of human tumor cell proliferation. As compared to indirubins bearing identical substituents but no hetero atoms in position 7 and 7', the activity of the compounds according to the present invention is increased and the propensity to get metabolized by CYP450s is reduced, resulting in improved metabolic stability.

  本发明涉及7-azaindirubins（1）、7'-azaindirubins（2）和7,7'-二氮杂吲哚（3），其中E、R1和R2的含义在描述中有详细说明，它们的制备和用作治疗癌症、神经退行性疾病、躁郁症、炎症和传染病，包括病毒性疾病的药物。根据结构的不同，这些吲哚作为抑制与肿瘤细胞生长有关的各种激酶的作用，尤其是作为人类肿瘤细胞增殖的抑制剂。与携带相同取代基但在位置7和7'没有杂原子的吲哚相比，根据本发明的化合物的活性增加，且通过CYP450酶代谢的倾向减少，从而提高了代谢稳定性。
• [EN] PHOSPHITYLATION PROCESS<br/>[FR] PROCEDE DE PHOSPHITYLATION
  申请人：AVECIA BIOTECHNOLOGY INC

  公开号：WO2004035599A1

  公开（公告）日：2004-04-29

  A process for the phosphitylation of an alcohol or thiol with a phosphitylation agent in the presence of an activator is provided. The activator has the formula (1): wherein p is 0 or an integer from 1 to 4 and R for each occurrence is a substituent. Preferably X7 is O and p is 0. The activator is commonly employed as a salt complex with an organic base. Preferred alcohols or thiols include nucleosides and oligonucleotides. The process is particularly suited for the synthesis of phosphoramidites.

  提供了一种在活化剂存在下，使用磷酰化试剂对醇或硫醇进行磷酰化的方法。活化剂具有公式（1）：其中p为0或1至4的整数，每次出现的R为取代基。最好X7为O，p为0。活化剂通常与有机碱形成盐络合物一起使用。首选的醇或硫醇包括核苷和寡核苷酸。该方法特别适用于磷酰胺酰胺的合成。
• I₂/CAN as a Mild and Efficient Reagent for Oxidative Csp³‐Csp² Cleavage of 3,3′‐Bis‐7‐azaindolylmethane: A Rapid One‐Pot Access to 3‐Formyl and 3‐Iodo‐7‐azaindoles
  作者：Pavithra Elavarasan、Sathananthan Kannadasan、Ponnusamy Shanmugam

  DOI：10.1002/ejoc.202300825

  日期：2024.1.22

  The combination of I2/CAN emerged as a mild and efficient reagent for oxidative Csp3-Csp2 cleavage of 3,3’-bis-7-azaindolylmethanes. The one-pot cleavage reaction affords 3-formyl and 3-iodo-7-azaindoles in an excellent combined yield. Based on the control experiments and literature, a plausible mechanism is postulated. Synthetic transformation of the products has also been described.

  I 2 /CAN 组合成为一种温和高效的试剂，用于氧化 Csp 3 -Csp 2 3,3'-bis-7- 裂解氮杂吲哚基甲烷。一锅裂解反应以优异的综合收率得到 3-甲酰基和 3-碘-7-氮杂吲哚。根据对照实验和文献，假设了一个合理的机制。还描述了产物的合成转化。
• Fluorination method
  申请人：Oxford University Innovation Limited

  公开号：US10287220B2

  公开（公告）日：2019-05-14

  The present invention relates to a process for producing an organic compound comprising an 18F atom. The compounds comprising an 18F can be useful as PET ligands for use in diagnostics and/or scanning. The process of the invention comprises treating an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp2 hybridized carbon atom, with (i) 18F— and (ii) a copper compound. The invention also provides the use of an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp2 hybridized carbon atom, in a process for producing an organic compound comprising an 18F atom, which process comprises treating the organoboron compound with (i)18F— and (ii) a copper compound. The invention also provides a compound of formula (XXXVII): wherein: each PGA is independently H or an alcohol protecting group; PGB is H or a carboxylic acid protecting group; each PGC is independently an amine protecting group; Z is a group selected from a boronic ester group, a boronic acid group, a borate group, and a trifluoroborate group; and a is an integer from 0 to 4.

  本发明涉及一种生产含有 18F 原子的有机化合物的工艺。含有 18F 的化合物可用作 PET 配体，用于诊断和/或扫描。本发明的工艺包括用(i)18F-和(ii)铜化合物处理有机硼化合物，该有机硼化合物包括与sp2杂化碳原子键合的硼原子。本发明还提供了有机硼化合物在生产包含 18F 原子的有机化合物的工艺中的用途，该有机硼化合物包含与 sp2 杂化碳原子键合的硼原子，该工艺包括用(i)18F- 和(ii)铜化合物处理该有机硼化合物。本发明还提供了式(XXXVII)的化合物： 其中：每个 PGA 独立地为 H 或醇保护基；PGB 为 H 或羧酸保护基；每个 PGC 独立地为胺保护基；Z 为选自硼酸酯基、硼酸基、硼酸盐基和三氟硼酸盐基的基团；以及 a 为 0 至 4 的整数。