2-Morpholino-methyl-benzofuran | 7419-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-Morpholino-methyl-benzofuran
• 英文别名: 2-Morpholinomethylbenzofuran；4-(1-benzofuran-2-ylmethyl)morpholine
• CAS: 7419-13-8
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: FTAVYUNYWZEZIV-UHFFFAOYSA-N

物化性质

• 熔点：
  50-51 °C
• 沸点：
  317.6±27.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯并呋喃-2-羧酸 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 lithium aluminium tetrahydride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 31.0h， 生成 2-Morpholino-methyl-benzofuran
  参考文献：
  名称：

  钯催化苯并呋喃-2-基甲基乙酸酯与亲核试剂的 Tsuji-Trost 型反应。

  摘要：

  研究了钯催化的苯并呋喃-2-基甲基乙酸酯与 N、S、O 和 C 软亲核试剂的类苄基亲核取代反应。反应的成功很大程度上取决于催化体系的选择：对于氮基亲核试剂，反应与 Pd2(dba)3/dppf 反应良好，而对于硫、氧和碳亲核试剂 [Pd(η3-C3H5)Cl] 2/XPhos 效率更高。区域化学结果表明，亲核取代仅发生在 η3-(苯并呋喃基)甲基配合物的苄位上。高至优异的产率和实验程序的简单性使该方案成为制备 2-取代苯并[b]呋喃的通用合成工具。

  DOI：

  10.1039/d0ra09601f

文献信息

• Substituted 3-cyanopyridines as protein kinase inhibitors
  申请人：Cole Cecil Derek

  公开号：US20070287708A1

  公开（公告）日：2007-12-13

  The present teachings provide compounds of formula I and their pharmaceutically acceptable salts, hydrates, and esters, wherein R 1 , R 2 , and X are as defined herein. The present teachings also provide methods of making the compounds of formula I, and methods of treating autoimmune and inflammatory diseases by administering a therapeutically effective amount of a compound or compounds of formula I to a mammal including a human.

  本发明的教导提供了公式I的化合物及其药用可接受的盐、水合物和酯，其中R1、R2和X如本文所述定义。本发明的教导还提供了制造公式I化合物的方法，以及通过向哺乳动物包括人类施用治疗有效量的公式I化合物或化合物来治疗自身免疫性和炎症性疾病的方法。
• Palladium-Catalyzed Substitution and Cross-Coupling of Benzylic Fluorides
  作者：George Blessley、Patrick Holden、Matthew Walker、John M. Brown、Véronique Gouverneur

  DOI：10.1021/ol300977f

  日期：2012.6.1

  Benzylic fluorides are suitable substrates for Pd(0)-catalyzed Tsuji–Trost substitution using carbon, nitrogen, oxygen, and sulfur nucleophiles and for cross-coupling with phenylboronic acid. For the bifunctional substrate 4-chlorobenzyl fluoride, fine-tuning of the reaction conditions allows for the regioselective displacement of either the chlorine or fluorine substituent. The leaving group ability

  苯甲酸氟化物是使用碳，氮，氧和硫亲核试剂进行Pd（0）催化的Tsuji-Trost取代以及与苯基硼酸交叉偶联的合适底物。对于双官能底物4-氯苄基氟化物，反应条件的微调允许氯或氟取代基的区域选择性置换。的氟化物VS在替代移位其它基团的离去基团的能力是CF 3 CO 2 ≈ p -NO 2 ç 6 ħ 4 CO 2 ≈OCO 2 CH 3 >˚F> CH 3 CO 2，其排名与Pd催化下的烯丙基氟化物相似。
• A novel route to 2-(dialkylaminomethyl)benzo[b]furans via a microwave-enhanced, solventless Mannich condensation–cyclization on cuprous iodide doped alumina
  作者：George W Kabalka、Lei Wang、Richard M Pagni

  DOI：10.1016/s0040-4039(01)01226-6

  日期：2001.8

  A microwave-enhanced, solventless Mannich condensation-cyclization Sequence involving the reaction of o-ethynylphenol with secondary amines and para-formaldehyde on cuprous iodide doped alumina it) the absence of solvents has been developed. The procedure generates 2-(dialkylaminomethyl)benzo[b]furans in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A microwave-enhanced, solventless Mannich condensation of terminal alkynes and secondary amines with para-formaldehyde on cuprous iodide doped alumina
  作者：George W. Kabalka、Li-Li Zhou、Lei Wang、Richard M. Pagni

  DOI：10.1016/j.tet.2005.10.049

  日期：2006.1

  A microwave-enhanced, solventless Mannich condensation of terminal alkynes and secondary amines with para-formaidehyde on cuprous iodide doped alumina has been developed. beta-Aminoalkynes are generated in good yields. The reaction can be extended to include a cyclization, which affords 2-substituted benzo[b]furans. The chemoselectivity of the reaction indicates that terminal alkynes are much more reactive than enolizable ketones under the reaction conditions. (c) 2005 Elsevier Ltd. All rights reserved.
• Ziegler,H.J. et al., Chimica Therapeutica, 1971, vol. 6, p. 159 - 166
  作者：Ziegler,H.J. et al.

  DOI：——

  日期：——