butyl 3-(benzylamino)propanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: butyl 3-(benzylamino)propanoate
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: GCWQNTQMKZNQGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙烯酸丁酯 、 苄胺 在 Candida antarctica lipase B 作用下， 以 甲苯 为溶剂， 反应 3.5h， 以59%的产率得到butyl 3-(benzylamino)propanoate
  参考文献：
  名称：

  通过胺的氮杂-迈克尔加成反应，混杂性假丝酵母南极脂肪酶B催化合成β-氨基酯

  摘要：

  已经开发出一种有效的方案，用于在60°C下使用CaL B作为生物催化剂与丙烯酸酯进行区域选择性氮杂-迈克尔加成胺。该反应适用于具有不同丙烯酸酯的各种伯胺和仲胺，从而以良好的产率合成相应的β-氨基酯。还研究了通过额外的酯交换步骤合成高级β-氨基酯的替代途径，并发现是有效的。

  DOI：

  10.1016/j.tetlet.2010.06.089

文献信息

• On-water magnetic NiFe₂O₄ nanoparticle-catalyzed Michael additions of active methylene compounds, aromatic/aliphatic amines, alcohols and thiols to conjugated alkenes
  作者：Soumen Payra、Arijit Saha、Subhash Banerjee

  DOI：10.1039/c6ra21160g

  日期：——

  Here, we have demonstrated the Michael addition of active methylene compounds, aromatic/aliphatic amines, thiols and alcohols to conjugated alkenes using magnetic nano-NiFe2O4 as reusable catalyst in water. Nano-NiFe2O4 efficiently catalyzed the formation of C–C and C–X (X = N, S, O etc.) bond through 1,4-addition reactions.

  在这里，我们已经证明了使用磁性纳米NiFe 2 O 4作为在水中可重复使用的催化剂将活性亚甲基化合物，芳香族/脂肪族胺，硫醇和醇的迈克尔加成到共轭烯烃上。纳米NiFe 2 O 4通过1，4-加成反应有效催化了CC和CX （X = N，S，O等）键的形成。
• Promiscuous Candida antarctica lipase B-catalyzed synthesis of β-amino esters via aza-Michael addition of amines to acrylates
  作者：Kishor P. Dhake、Pawan J. Tambade、Rekha S. Singhal、Bhalchandra M. Bhanage

  DOI：10.1016/j.tetlet.2010.06.089

  日期：2010.8

  has been developed. The reaction is applicable to a wide variety of primary and secondary amines with different acrylates to synthesize the corresponding β-amino esters with good yields. An alternative route for the synthesis of higher β-amino esters through the additional transesterification step is also studied and was found effective.

  已经开发出一种有效的方案，用于在60°C下使用CaL B作为生物催化剂与丙烯酸酯进行区域选择性氮杂-迈克尔加成胺。该反应适用于具有不同丙烯酸酯的各种伯胺和仲胺，从而以良好的产率合成相应的β-氨基酯。还研究了通过额外的酯交换步骤合成高级β-氨基酯的替代途径，并发现是有效的。
• Uncatalysed intermolecular aza-Michael reactions
  作者：Florian Medina、Nathalie Duhal、Christophe Michon、Francine Agbossou-Niedercorn

  DOI：10.1016/j.crci.2012.11.001

  日期：2013.4

  Résumé The catalyst-free reactions of activated alkenes with primary and secondary amines were investigated leading to various mono- and di-hydroamination products, the latter being rare and original. These reactions were shown to depend first on the strength of the nucleophile. Temperature and steric hindrance of the reagents were the other key factors controlling the selectivity of these aza-Michael reactions. In spite of their poor nucleophilicities, some N-heterocyclic amines could react with different activated alkenes affording valuable intermediates. Such results tended to demonstrate the hydrogen-bonding interactions between activated alkenes and poly-nitrogen aromatic cycles may control these concerted or fully conjugate aza-Michael additions. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.doc

  简历 摘要 研究了活性烯烃与一级和二级胺的无催化剂反应，生成多种单氢胺化和双氢胺化产物，后者较为罕见且具有原创性。这些反应首先取决于亲核试剂的强度。温度和试剂的立体阻碍是控制这些氮杂迈克尔反应选择性的其他关键因素。尽管某些含氮杂环胺的亲核性较差，但它们仍能与不同的活性烯烃反应，生成有价值的中间体。这些结果倾向于表明，活性烯烃与多氮芳香环之间的氢键相互作用可能控制这些协同或完全共轭的氮杂迈克尔加成反应。 补充材料： 本文的补充材料以单独文件提供： mmc1.doc
• Intermolecular Mono- and Dihydroamination of Activated Alkenes Using a Recoverable Gold Catalyst
  作者：Florian Medina、Christophe Michon、Francine Agbossou-Niedercorn

  DOI：10.1002/ejoc.201200891

  日期：2012.11

  A combination of gold chloride organometallic complex and a silver salt was used to catalyze intermolecular hydroamination of activated alkenes, i.e aza-Michael reactions. The gold-catalyzed reactions of activated alkenes with nitrogen substrates were investigated and found to afford various mono- and dihydroamination products, the latter being rare and original. After flash chromatography, gold NHC

  氯化金有机金属络合物和银盐的组合用于催化活化烯烃的分子间加氢胺化，即氮杂-迈克尔反应。研究了活化烯烃与氮底物的金催化反应，发现可以提供各种单氢胺化和二氢胺化产物，后者是罕见的和原始的。快速色谱后，金 NHC 催化剂可以作为氢氧化金 NHC 复合物回收。当与银盐结合时，金络合物再次导致活性加氢胺化催化剂。
• Ruthenium‐ and Rhodium‐Catalyzed Dehydrogenative <i>ortho</i> ‐Alkenylation of Benzylamines <i>via</i> Free Amino Group Directed CH Bond Cleavage
  作者：Chiharu Suzuki、Keisuke Morimoto、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1002/adsc.201400088

  日期：2014.5.5

  The dehydrogenative direct coupling of α,α‐disubstituted benzylamines with acrylates takes place efficiently at room temperature under ruthenium catalysis, accompanied by free amino group‐directed ortho‐alkenylation and successive cyclization to produce (isoindol‐1‐yl)acetic acid derivatives. The reactions using styrenes in place of acrylates proceed effectively in the presence of a rhodium catalyst

  α，α-二取代苄胺与丙烯酸酯的脱氢直接偶联反应在室温下钌催化下有效进行，伴随有游离氨基定向的邻链烯基化反应和连续环化反应生成（异吲哚-1-基）乙酸衍生物。使用苯乙烯代替丙烯酸酯的反应在铑催化剂而不是钌的存在下有效地进行。