N-tert-butyl-N-furan-3-ylmethylamine | 1027904-74-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-tert-butyl-N-furan-3-ylmethylamine
• 英文别名: N-(furan-3-ylmethyl)-2-methylpropan-2-amine
• CAS: 1027904-74-0
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: AQHBVQVKVWXNPK-UHFFFAOYSA-N

物化性质

• 沸点：
  184.7±15.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-N-furan-3-ylmethylamine 在 titanium(III) chloride 、 草酰氯 、 双氧水 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 水 、 乙腈 、 苯 为溶剂， 反应 2.17h， 生成 N-tert-butyl-N-(furan-3-ylmethyl)-2-[2-(4-methylphenyl)sulfinylphenyl]acetamide
  参考文献：
  名称：

  Additive and Vinylogous Pummerer Reactions of Amido Sulfoxides and Their Use in the Preparation of Nitrogen Containing Heterocycles

  摘要：

  The alpha-thiocarbocation generated from the Pummerer re action of N-methyl-N-phenyl-2-[2-(toluene-4-sulfinyl)phenyl]acetamide undergoes Friedel-Crafts reaction at the gamma-carbon with the tethered aromatic ring. Reductive removal of the phenylthio group from the resulting product using Raney nickel occurs in high yield, and the overall reaction represents a new method for the synthesis of a variety of 3-phenyl-substituted oxindoles. Treatment of the related N-benzyl-N-alkyl amido sulfoxide system with trifluoroacetic anhydride affords tetrahydroisoquinolone derivatives. The product distribution encountered coincides with the rotamer population of the starting amide. When the N-benzyl-N-methyl amide is used, only the normal Pummerer product is formed. In this case, the thionium ion is generated in the wrong conformation for pi-cyclization to occur. The corresponding N-tert-butyl amido system, however, exists in a geometric orientation which places the benzylic group in the crucial conformation necessary for pi-cyclization, and consequently, the reaction proceeds smoothly. Related cyclization reactions occur in good yield with the corresponding furanyl and cyclohexenyl N-tert-butyl amido sulfoxides. The additive Pummerer reaction of 3-phenylsulfinyl-N-benzyl-N-tert-butylacrylamide gave products derived from both 5- and 6-exo trig cyclizations. Intramolecular electrophilic aromatic substitution via six-membered ring closure ultimately afforded a dihydropyridone. The competitive process involving ipso attack of the aromatic ring on the thionium ion generates a spiro cyclohexadienyl cation that undergoes fragmentation of the adjacent a-bond. The resulting acyl iminium ion is converted to N-tert-butyl-2-phenyl-3-phenylsulfinylacrylamide upon aqueous workup. Only cyclizations leading to five-membered rings occur with the corresponding indolyl and alkenyl N-tert-butyl amido sulfoxides.

  DOI：

  10.1021/jo972093h
• 作为产物：
  描述：

  3-呋喃甲醇 在 三溴化磷 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 N-tert-butyl-N-furan-3-ylmethylamine
  参考文献：
  名称：

  溴氧化反应制得的3-糠基胺中的3-甲酰基吡咯

  摘要：

  在丙酮-水溶液中用溴氧化3-糠胺3a-e得到高收率的N-取代的3-甲酰基吡咯4a-e。提出了通过Clauson-Kaas反应的反应机理，然后通过2-烯-1,4-二酮13和14的顺反异构化来解释吡咯4a-e的形成。

  DOI：

  10.1002/jccs.201000195

文献信息

• Access to β-Lactams by Enantioselective Palladium(0)-Catalyzed C(sp³)H Alkylation
  作者：Julia Pedroni、Michele Boghi、Tanguy Saget、Nicolai Cramer

  DOI：10.1002/anie.201405508

  日期：2014.8.18

  Reported here is an asymmetric CH functionalization approach to β‐lactams using readily accessible chloroacetamide substrates. Important aspects of this transformation are challenging C(sp3)C(sp3) and strain‐building reductive eliminations to for the four‐membered ring. In general, the β‐lactams are formed in excellent yields and enantioselectivities using a bulky taddol phosphoramidite ligand in combination

  β-内酰胺由于具有广泛的生物学活性以及易于发生开环反应，因此是非常重要的结构基序。过渡金属催化的CH功能化已成为实现非常规高效断开连接的策略。与Pd 0催化的CH官能化用于芳基-芳基偶联的显着进展相反，涉及形成饱和C（sp 3）C（sp 3）键的相关反应是难以捉摸的。这里报告的是一个不对称的C使用容易获得的氯乙酰胺底物对β-内酰胺进行H官能化方法。这种转变的重要方面是挑战四元环的C（sp 3）C（sp 3）和应变消除。通常，使用大体积的他达酚亚磷酰胺配体与金刚烷基羧酸作为助催化剂，可以以优异的收率和对映选择性形成β-内酰胺。
• TRICYCLIC PYRIDO-CARBOXAMIDE DERIVATIVES AS ROCK INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160152628A1

  公开（公告）日：2016-06-02

  The present invention provides compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective ROCK inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating cardiovascular, smooth muscle, oncologic, neuropathologic, autoimmune, fibrotic, and/or inflammatory disorders using the same.

  本发明提供了式（I）的化合物：或其立体异构体，互变异构体或药学上可接受的盐，其中所有变量如本文所定义。这些化合物是选择性ROCK抑制剂。本发明还涉及包含这些化合物的制药组合物以及使用它们治疗心血管，平滑肌，肿瘤，神经病理，自身免疫，纤维化和/或炎症性疾病的方法。
• Indolone compounds and their use as AMPA receptor modulators
  申请人：Janssen Pharmaceutica NV

  公开号：US10604484B2

  公开（公告）日：2020-03-31

  Provided herein are compounds of Formula (I), and pharmaceutically acceptable salts, N-oxides, or solvates thereof, Also provided herein are pharmaceutical compositions, comprising compounds of Formula (I), and methods of using compounds of Formula (I).

  本文提供的是式 (I) 化合物及其药学上可接受的盐、N-氧化物或溶解物、 本文还提供了包含式（I）化合物的药物组合物，以及使用式（I）化合物的方法。
• METHODS, COMPOUNDS, AND COMPOSITIONS FOR REDUCING BODY FAT AND MODULATING FATTY ACID METABOLISM
  申请人：Piomelli Daniele

  公开号：US20090005447A1

  公开（公告）日：2009-01-01

  Methods, pharmaceutical compositions, and compounds for reducing body weight, modulating body lipid metabolism, and reducing food intake in mammals are provided. The compounds of the invention include fatty acid ethanolamide compounds, homologues and analogs of which the prototype is the endogenous fatty acid ethanolamide, oleoylethanolamide.
• INDOLONE COMPOUNDS AND THEIR USE AS AMPA RECEPTOR MODULATORS
  申请人：Janssen Pharmaceutica NV

  公开号：US20180118683A1

  公开（公告）日：2018-05-03

  Provided herein are compounds of Formula (I), and pharmaceutically acceptable salts, N-oxides, or solvates thereof, Also provided herein are pharmaceutical compositions, comprising compounds of Formula (I), and methods of using compounds of Formula (I).