1-(4,4-diethoxybutyl)piperidine | 97103-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(4,4-diethoxybutyl)piperidine
• 英文别名: N-(4,4-diethoxybutyl)piperidine；4-(N-piperidino)butyraldehyde diethyl acetal；4-Piperidino-1,1-diaethoxy-butan；1-(4,4-Diethoxybutyl)-piperidine
• CAS: 97103-89-4
• 化学式: C₁₃H₂₇NO₂
• 分子量: 229.363
• InChiKey: VLZFAXIVYZBUET-UHFFFAOYSA-N

物化性质

• 沸点：
  112-115 °C(Press: 13 Torr)
• 密度：
  0.9159 g/cm3(Temp: 19 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(3-氯丙基)哌啶 、 原甲酸三乙酯 在 碘 、 magnesium 作用下， 以 环己烷 为溶剂， 反应 5.33h， 以70%的产率得到1-(4,4-diethoxybutyl)piperidine
  参考文献：
  名称：

  [EN] PREPARATION OF 4-(N, N-DISUBSTITUTEDAMINO) BUTYRALDEHYDE ACETALS
  [FR] PROCEDE AMELIORE POUR L'ELABORATION D'ACETALS DE 4-(N, N-AMINODISUBSTITUE) BUTYRALDEHYDE

  摘要：

  公开号：

  WO2003101931A3

文献信息

• Efficient and Regioselective Ruthenium-catalyzed Hydro-aminomethylation of Olefins
  作者：Lipeng Wu、Ivana Fleischer、Ralf Jackstell、Matthias Beller

  DOI：10.1021/ja312271c

  日期：2013.3.13

  An efficient and regioselective ruthenium-catalyzed hydroaminomethlyation of olefins is reported. Key to success is the use of specific 2-phosphino-substituted imidazole ligands and triruthenium dodecacarbonyl as catalyst. Both industrially important aliphatic as well as various functionalized olefins react with primary and secondary amines to give the corresponding secondary and tertiary amines generally in high yields (up to 96%) and excellent regioselectivities (n/iso up to 99:1).
• Amines Made Easily:  A Highly Selective Hydroaminomethylation of Olefins
  作者：Moballigh Ahmed、Abdul Majeed Seayad、Ralf Jackstell、Matthias Beller

  DOI：10.1021/ja030143w

  日期：2003.8.1

  A highly chemo- and regioselective hydroaminomethylation of simple as well as functionalized alpha-olefins using a cationic rhodium precatalyst together with Xantphos as ligand is reported. Studies of the influence of ligands and reaction conditions led to an unprecedented selective hydroaminomethylation procedure. The novel procedure constitutes an economically attractive and environmentally favorable synthesis of secondary and tertiary aliphatic amines.
• PHOSPHOR-LIGANDEN UND VERFAHREN ZUR SELEKTIVEN RUTHENIUM-KATALYSIERTEN HYDROAMINOMETHYLIERUNG VON OLEFINEN
  申请人：Evonik Degussa GmbH

  公开号：EP2951188A1

  公开（公告）日：2015-12-09
• [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF 4-(N, N-DISUBSTITUTEDAMINO) BUTYRALDEHYDE ACETALS<br/>[FR] PROCEDE AMELIORE POUR L'ELABORATION D'ACETALS DE 4-(N, N-AMINODISUBSTITUE) BUTYRALDEHYDE
  申请人：NATCO PHARMA LTD

  公开号：WO2003101931A2

  公开（公告）日：2003-12-11

  The invention disclosed in this application relates to an improved process for the preparation of compounds of formula (I): R1R2NCH2CH2CH2CH(OR3)2; wherein, R1 = R2 = C1-C16 alkyl; C3-C7 cycloalkyl; R1 = C1-C16 alkyl; R2 = C3-C7 cycloalkyl; NR1R2 = pyrrolidino, piperidino, morpholino, thiomorpholino, R1 = C1-C6 alkyl; R2 = ArCH2; Ar =4-R4-C6H4-, R4 = MeO, EtO, Me, Et, NMe2, NEt2, SMe, SEt, etc; R3=C1-C6 alkyl; C3-C7 cycloalkyl which comprises: (i) Reacting 3-(N, N-disubstitutedamino)propyl halide of formula (XXI): R1R2NCH2CH2CH2X; wherein, R1, R2 = as defined above, X = C1 or Br, with magnesium in the presence of a solvent to get the Grrgnard reagent 3-(N, N-disubstitutedamino)-propylmagnesium halide; (ii) Reacting the resulting 3-(N, N-disubstitutedamino) propylmagnesium halide (Grignard reagent) with the trisubstituted orthoformate of formula (XVII): HC(OR5)(OR3)2; wherein, R3 and R5 is same or different and represent C1 to C6 alkyl, C3 to C7 cycloalkyl OR R3 is as defined above and R5 represents phenyl radical; (iii) Filtering off the resultant reaction mixture and distilling the filtrate to isolate the compound of the formula (I). These substituted butyraldehyde derivatives of the formula (I) are very important building blocks for the synthesis of various tryptamine derivatives. In particular 4-(N, N-dimethylamino)butyraldehyde dimethyl or diethyl acetals are crucial intermediates for the synthesis of commercially available anti-migraine drugs, like sumatriptan, zolmitriptan, and rizatriptan.
• [DE] PHOSPHOR-LIGANDEN UND VERFAHREN ZUR SELEKTIVEN RUTHENIUM-KATALYSIERTEN HYDROAMINOMETHYLIERUNG VON OLEFINEN<br/>[EN] PHOSPHORUS LIGANDS AND METHOD FOR THE SELECTIVE RUTHENIUM-CATALYZED HYDROAMINOMETHYLATION OF OLEFINS<br/>[FR] LIGAND PHOSPHORÉ ET PROCÉDÉ D'HYDROAMINOMÉTHYLATION SÉLECTIVE D'OLÉFINES, CATALYSÉE PAR RUTHÉNIUM
  申请人：EVONIK INDUSTRIES AG

  公开号：WO2014118038A1

  公开（公告）日：2014-08-07

  Neue Phosphor-Liganden und ein chemo- und regioselektives Verfahren zur Hydroaminomethylierung von Olefinen mit mindestens einem primären oder sekundären Amin unter Zuführung von H2 und CO unter katalytischen Bedingungen in Gegenwart eines Ruthenium- Komplexes und eines organischen Phosphor-Liganden.