6-(but-3-enyl)-piperidin-2-one | 155193-69-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 6-(but-3-enyl)-piperidin-2-one
• 英文别名: 6-(But-3-enyl)piperidin-2-one；6-(3-butenyl)-2-piperidinone；6-But-3-enylpiperidin-2-one
• CAS: 155193-69-4
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: FLLVJKGINMVMTH-UHFFFAOYSA-N

物化性质

• 熔点：
  32-34 °C
• 沸点：
  292.5±9.0 °C(Predicted)
• 密度：
  0.930±0.06 g/cm3(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：
  0.67
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(but-3-enyl)-piperidin-2-one 在 六甲基磷酰三胺 、 正丁基锂 、 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.75h， 生成 2-(3-butenyl)-6-(2-propenyl)-1-piperidinecarboxylic acid phenylmethyl ester
  参考文献：
  名称：

  通过闭环烯烃复分解合成桥连氮杂双环结构。

  摘要：

  已经开发了一种简便合成氮杂双环[mn1]烯烃（m = 3-5; n = 3，2）的新策略，该策略涉及顺式-2,6-二烯基-N的闭环易位（RCM）反应。 -酰基哌啶衍生物。从戊二酰亚胺（11）开始的六步中或从4-甲氧基吡啶（25）开始的三步中可以容易地制备必需的2，6-二烯基哌啶。在确定该方法实用性的一个实例中，制备了官能化的8-氮杂双环[3.2.1]辛烷32，其是合成各种托烷生物碱的潜在中间体。另外，已经开发出构建桥接的四氢-β-咔啉环系统5的新途径，其特征在于烯炔45的闭环易位以在46中构建桥环。到46的这种简明路线还具有潜在的通用性和有用的程序，用于从酯官能团一步制备末端炔烃。46中乙烯基的选择性氧化提供了不饱和醛47，其可以用作合成几种Sarpagine生物碱的有用中间体。

  DOI：

  10.1021/jo0349936
• 作为产物：
  描述：

  6-乙氧基哌啶-2-酮 在 甲酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.0h， 生成 6-(but-3-enyl)-piperidin-2-one
  参考文献：
  名称：

  A ring-closing olefin metathesis approach to bridged azabicyclic structures

  摘要：

  A facile and general entry to functionalized bridged bicyclic nitrogen heterocycles has been developed that involves the ring-closing metathesis (RCM) of cis-2,6-dialkenyl-N-acyl piperidines that were readily prepared from glutarimide or 4-methoxypyridine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00100-4

文献信息

• Intramolecular amidocyclopropanation reactions using diethoxymethyl-functionalised lactams as organozinc carbenoid precursors
  作者：Laure Jerome、Tom D. Sheppard、Abil E. Aliev、William B. Motherwell

  DOI：10.1016/j.tetlet.2009.03.224

  日期：2009.7

  Intramolecular amidocyclopropanation reactions of diethoxymethyl-lactams containing a pendant alkene were examined using zinc/TMSCI. With a range of 4-6-membered lactams, bicyclic amidocyclopropanes were obtained with very high diastereoselectivity with a preference for the formation of the More hindered endo-cyclopropane. (C) 2009 Elsevier Ltd. All rights reserved.
• Studies on the Intramolecular Cycloaddition Reaction of Mesoionics Derived from the Rhodium(II)-Catalyzed Cyclization of Diazoimides
  作者：Albert Padwa、Donald L. Hertzog、William R. Nadler、Martin H. Osterhout、Alan T. Price

  DOI：10.1021/jo00085a035

  日期：1994.3

  A series of alkenyl-substituted imides were prepared by treating the appropriate amide with 2,2,6-trimethyl-4H-1,3-dioxen-4-one in xylene at 140-degrees-C to give the N-acetoacylated imides. Exposure of these imides to standard diazo transfer conditions gave the desired diazoimides. The carbenoid intermediate derived by treatment of the diazoimide with rhodium(II) acetate undergoes ready cyclization onto the neighboring amide carbonyl oxygen atom to generate an isomunchnone intermediate. Subsequent 1,3-dipolar cycloaddition across the pendant olefin affords the cycloadduct in high yield. The stereochemical assignment of several of the cycloadducts was deduced by X-ray crystallography. The stereochemical outcome of the reaction is the consequence of an endo cycloaddition of the neighboring pi-bond across the transient isomunchnone dipole. Molecular mechanics calculations were used to model energy differences between the endo and exo diastereomers. The calculations reveal that the endo diastereomers are significantly (8-12 kcal/mol) lower in energy than the corresponding exo isomers thereby providing a rationale for the preferred endo cycloaddition. Ring opening of the cycloadducts occurred readily producing a transient N-acyliminium ion which either lost a proton to give an enamide or was reduced by Et3SiH to afford a bicyclic piperidine ring.