3-(N-t-butylaminomethyl)-1-methylindole | 130539-86-5

• 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: 3-(N-t-butylaminomethyl)-1-methylindole
• 英文别名: 2-methyl-N-[(1-methylindol-3-yl)methyl]propan-2-amine
• CAS: 130539-86-5
• 化学式: C₁₄H₂₀N₂
• 分子量: 216.326
• InChiKey: RLASLJGWTKZVBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  17
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(N-t-butylaminomethyl)-1-methylindole 在 草酰氯 、 N,N-二甲基甲酰胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 (Z)-3-Benzenesulfinyl-N-tert-butyl-N-(1-methyl-1H-indol-3-ylmethyl)-acrylamide
  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：

  1-甲基吲哚-3-甲醛 、 叔丁胺 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 13.0h， 生成 3-(N-t-butylaminomethyl)-1-methylindole
  参考文献：
  名称：

  AgF介导的活化烯烃的二烷基化：有效地获得含腈的螺氧杂吲哚

  摘要：

  公开了一种新型的由Ag介导的烯烃二烷基化反应，其中AgF对于激活乙腈的CH键至关重要。该反应为从现成的（1 H-吲哚-3-基）甲胺衍生物中制取含腈的螺硫辛醇提供了一种有效的方法。

  DOI：

  10.1002/cjoc.201400350

文献信息

• A new route to secondary amines from bis-(alkoxymethyl)-alkylamines - the activation of an aminomethyl group and protection of the product by the same functional group
  作者：Martyn J. Earle、Robin A. Fairhurst、Harry Heaney、George Papageorgiou、Robert F. Wilkins

  DOI：10.1016/s0040-4039(00)97589-0

  日期：1990.1

  variety of acidic reagents affords good yields of N-alkoxymethyl-N-alkylmethyleneiminium salts which react with trimethylsilyl enol ethers, and nucleophilic aromatic substrates to form protected secondary amines or tertiary amines by domino reactions; silyl ketene acetals afford tertiary amines only.

  的治疗N，N- -双用各种酸性试剂，得到良好的产率的（烷氧基）烷基胺Ñ -alkoxymethyl- Ñ -alkylmethyleneiminium盐，其与三甲基甲硅烷烯醇醚反应，亲核芳族底物，通过多米诺形式保护的仲胺或叔胺反应; 甲硅烷基乙烯酮缩醛仅提供叔胺。
• 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。
• The use of bis(aminol) ethers derived from aliphatic primary amines in the synthesis of secondary and tertiary amines
  作者：Harry Heaney、George Papageorgiou

  DOI：10.1016/0040-4020(96)00026-9

  日期：1996.3

  prepared from primary aliphatic amines and benzylamine together with formaldehyde and either ethanol or methanol; they were reacted with electrophiles to give N-alkyl-N-alkoxymethyl-methyleneiminium salts which gave mixtures of secondary and tertiary amines in reactions with electron rich aromatic compounds: sequential reactions with two different nucleophiles gave the expected tertiary amines.

  由脂族伯胺和苄胺与甲醛，乙醇或甲醇一起制备了一系列双（氨基）醚。它们与亲电试剂反应，得到N-烷基-N-烷氧基甲基-亚甲基亚胺盐，在与富电子芳族化合物的反应中生成仲胺和叔胺的混合物：与两种不同亲核试剂的顺序反应得到了预期的叔胺。
• Novel Lipopeptides as Antibacterial Agents
  申请人：Hill Jason

  公开号：US20090011977A1

  公开（公告）日：2009-01-08

  The present invention relates to novel lipopeptide compounds. The invention also relates to pharmaceutical compositions of these compounds and methods of using these compounds as antibacterial compounds. The invention also relates to methods of producing these novel lipopeptide compounds and intermediates used in producing these compounds.

  本发明涉及新型脂肽化合物。本发明还涉及这些化合物的药物组合物以及将这些化合物用作抗菌化合物的方法。本发明还涉及生产这些新型脂肽化合物的方法以及用于生产这些化合物的中间体。
• EARLE, MARTYN J.;FAIRHURST, ROBIN A.;HEANEY, HARRY;PAPAGEORGIOU, GEORGE;W+, TETRAHEDRON LETT., 31,(1990) N9, C. 4229-4232
  作者：EARLE, MARTYN J.、FAIRHURST, ROBIN A.、HEANEY, HARRY、PAPAGEORGIOU, GEORGE、W+

  DOI：——

  日期：——