N-allyl-5-hydroxypentanamide | 133055-24-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-allyl-5-hydroxypentanamide
• 英文别名: 5-hydroxy-N-prop-2-enylpentanamide
• CAS: 133055-24-0
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: YKPTYZNHBLIJSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-allyl-5-hydroxypentanamide 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以67%的产率得到5-allylamino-1-pentanol
  参考文献：
  名称：

  胺与内酯/酯的还原性羟烷基化/烷基化†

  摘要：

  我们已经开发出一种一锅法，使用内酯或酯作为羟烷基化/烷基化试剂，直接进行胺的分子间还原性羟烷基化或烷基化。该方法基于内酯/酯与DIBAL-H-胺络合物（对于伯胺）或DIBAL-H-胺盐酸盐复合物（对于仲胺）原位酰胺化，然后将酰胺还原成过量的DIBAL-H。与用DIBAL-H还原生成醛的Weinreb酰胺不同，原位形成的Weinreb酰胺的还原产生了胺。而且，该方法不仅限于Weinreb酰胺，它也适用于其他酰胺一般。建议采用合理的机制解释反应的结果。

  DOI：

  10.1039/c2ob25901j
• 作为产物：
  描述：

  delta-戊内酯 、 丙烯胺 以100%的产率得到N-allyl-5-hydroxypentanamide
  参考文献：
  名称：

  在非氧化条件下生成和捕获烯烃自由基阳离子：通过外模和内模环化形成六元环。

  摘要：

  [反应：参见正文]已证明，由β-（磷酸氧基）烷基自由基的离子断裂产生的烯烃自由基阳离子在6-exo或6-endo模式下被胺有效地亲核捕获，从而导致六元模式氮杂环。烯烃的适当放置能够使自由基环化并置，导致形成吲哚并立啶和1-氮杂双环[3.2.1]辛烷骨架。

  DOI：

  10.1021/ol026204x

文献信息

• Generation and Trapping of Alkene Radical Cations under Nonoxidizing Conditions:  Formation of Six-Membered Rings by <i>E</i><i>xo</i>- and <i>E</i><i>ndo</i>-Mode Cyclizations
  作者：David Crich、Santhosh Neelamkavil

  DOI：10.1021/ol026204x

  日期：2002.7.1

  [reaction: see text] It is demonstrated that alkene radical cations generated by the radical ionic fragmentation of beta-(phosphatoxy)alkyl radicals undergo efficient nucleophilic capture by amines in either the 6-exo or 6-endo modes, leading to six-membered nitrogen heterocycles. Suitable placement of an alkene enables the juxtaposition of a radical cyclization resulting in the formation of both the

  [反应：参见正文]已证明，由β-（磷酸氧基）烷基自由基的离子断裂产生的烯烃自由基阳离子在6-exo或6-endo模式下被胺有效地亲核捕获，从而导致六元模式氮杂环。烯烃的适当放置能够使自由基环化并置，导致形成吲哚并立啶和1-氮杂双环[3.2.1]辛烷骨架。
• Rearrangements of Substituted 3-Aza-1,2,5-hexatrienes. 3. The Scope and Versatility of an Extremely Mild 3-Aza-Cope Reaction
  作者：Michael A. Walters、Andrew B. Hoem、Colleen S. McDonough

  DOI：10.1021/jo951587g

  日期：1996.1.1

  An investigation of the [3,3]-sigmatropic reaction of substituted 3-aza-1,2,5-hexatrienes to give 4-pentenenitriles is presented. This reaction has been found to occur under a wide variety of reactions conditions (10 are reported) starting from readily available N-allylamides. In contrast to other 3-aza-Cope reactions, this process occurs at room temperature, under essentially neutral conditions, allowing for the facile preparation of substituted nitrile products in moderate to excellent yields. The scope and versatility of this reaction are demonstrated by its use on a wide variety of substrates, including nitrogen- and oxygen-substituted amides. The rearrangements of cis- and trans-4-tert-butyl-N-allylcyclohexanecarboxamides 16a and 16b are reported and were found to give a ratio of axial to equatorial (A:E) products consistent with A:E ratios found for other related sigmatropic reactions. The stereochemical requirements for this reaction appear to be similar to other [3,3]-rearrangements even though the transition state for this rearrangement is most likely neither boat nor chairlike.
• An extremely mild 3-aza-Claisen reaction. 1. Rearrangement of simple N-allylamides.
  作者：Michael A. Walters、Colleen S. McDonough、Perry S. Brown、Andrew B. Hoem

  DOI：10.1016/0040-4039(91)80848-z

  日期：1991.1

  An extremely mild 3-aza-Claisen reaction has been developed. Readily available N-allyl amides are converted to pentenylnitriles in moderate to good yields by a transformation that occurs at room temperature under essentially neutral conditions.
• Reductive hydroxyalkylation/alkylation of amines with lactones/esters
  作者：Yu-Huang Wang、Jian-Liang Ye、Ai-E Wang、Pei-Qiang Huang

  DOI：10.1039/c2ob25901j

  日期：——

  We have developed a one-pot method for the direct intermolecular reductive hydroxyalkylation or alkylation of amines using lactones or esters as the hydroxyalkylating/alkylating reagents. The method is based on the in situ amidation of lactones/esters with DIBAL-H–amine complex (for primary amines) or DIBAL-H–amine hydrochloride salt complex (for secondary amines), followed by reduction of the amides

  我们已经开发出一种一锅法，使用内酯或酯作为羟烷基化/烷基化试剂，直接进行胺的分子间还原性羟烷基化或烷基化。该方法基于内酯/酯与DIBAL-H-胺络合物（对于伯胺）或DIBAL-H-胺盐酸盐复合物（对于仲胺）原位酰胺化，然后将酰胺还原成过量的DIBAL-H。与用DIBAL-H还原生成醛的Weinreb酰胺不同，原位形成的Weinreb酰胺的还原产生了胺。而且，该方法不仅限于Weinreb酰胺，它也适用于其他酰胺一般。建议采用合理的机制解释反应的结果。
• LiNTf₂-Catalyzed Aminolysis of Lactones with Stoichiometric Quantities of Amines
  作者：Antonio Guarna、Claudia Lalli、Andrea Trabocchi、Gloria Menchi

  DOI：10.1055/s-2007-1000882

  日期：2008.1

  LiNTf2 in the reaction of lactones with amines is able to activate cyclic esters towards ring opening, thus leading to clean open-chain amides under mild conditions and using a stoichiometric amount of amine. The generality of the method was demonstrated by a range of selected lactones and amines.

  在内酯与胺的反应中，LiNTf2 能够活化环酯，使其向开环方向发展，从而在温和的条件下，使用一定量的胺就能生成干净的开链酰胺。一系列选定的内酯和胺证明了该方法的通用性。