N-allyl-N-phenethylacrylamide | 1429218-10-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-allyl-N-phenethylacrylamide
• 英文别名: ethylene phenyl N-allyl-N-acrylamide；N-(2-phenylethyl)-N-prop-2-enylprop-2-enamide
• CAS: 1429218-10-9
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: CZGAJLXZSKZEMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-allyl-N-phenethylacrylamide 、 苯甲醛 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 硼酸 作用下， 以 间二甲苯 为溶剂， 反应 3.0h， 以17%的产率得到(E)-3-benzylidene-1-phenethyl-1H-pyrrol-2(3H)-one
  参考文献：
  名称：

  Tandem Ring-Closing Metathesis/Isomerization Reactions for the Total Synthesis of Violacein

  摘要：

  A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.

  DOI：

  10.1021/ol400654r
• 作为产物：
  描述：

  乙基溴苯 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 N-allyl-N-phenethylacrylamide
  参考文献：
  名称：

  Tandem Ring-Closing Metathesis/Isomerization Reactions for the Total Synthesis of Violacein

  摘要：

  A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.

  DOI：

  10.1021/ol400654r

文献信息

• Decomplexation as a rate limitation in the thiol-Michael addition of <i>N</i>-acrylamides
  作者：Joseph S. Brown、Andrew W. Ruttinger、Akash J. Vaidya、Christopher A. Alabi、Paulette Clancy

  DOI：10.1039/d0ob00726a

  日期：——

  modification. Here, we combined experimental and quantum mechanical modeling approaches using density functional theory (DFT) to examine the thiol-Michael reaction of N-allyl-N-acrylamide monomers used to prepare sequence-defined oligothioetheramides (oligoTEAs). Experimentally, the reaction was evaluated with two fluorous tagged thiols and several monomers at room temperature (22 °C and 40 °C). Using the Eyring

  硫醇-迈克尔加成是一种流行的、选择性的、高产率的“点击”反应，可用于从小分子合成到聚合物或表面改性的各种应用。在这里，我们使用密度泛函理论 (DFT) 结合实验和量子力学建模方法来检查用于制备序列定义的低聚硫醚酰胺 (oligoTEA)的N-烯丙基-N-丙烯酰胺单体的硫醇-迈克尔反应。在实验上，该反应在室温（22 °C 和 40 °C）下用两种氟标记的硫醇和几种单体进行了评估。使用 Eyring 方程计算活化能（焓），观察到从 28 kJ mol -1到 108 kJ mol -1的广泛能垒在同一烯烃类中。在计算上，DFT 与 Nudged Elastic Band 方法结合使用 B97-D3 泛函和混合隐式-显式甲醇溶剂化方法计算每个单体反应的整个反应坐标。硫醇-迈克尔反应传统上受到传播或链转移步骤的限速。但是，我们的测试用例N-丙烯酰胺和氟硫醇显示实验和计算数据产生令人满意的一致性，只
• Sequence-defined polymers and methods of making same and using same
  申请人：Cornell University

  公开号：US11384205B2

  公开（公告）日：2022-07-12

  Methods of making sequence-defined polymers and sequence-defined polymers. The methods are based on the orthogonal reactivity of monomers having at least two different functional groups. The sequence-defined polymers can be used in various applications. For example, the SDPs (e.g., pH sensitive SDPs) are used in cell lysis methods or as molecular vehicles to transport drug cargo into cells.

  制造序列确定的聚合物和序列确定的聚合物的方法。这些方法基于至少具有两种不同官能团的单体的正交反应性。序列确定的聚合物可用于各种用途。例如，序列定义聚合物（如 pH 敏感序列定义聚合物）可用于细胞裂解方法或作为分子载体将药物运送到细胞中。
• Sequence-Defined Polymers via Orthogonal Allyl Acrylamide Building Blocks
  作者：Mintu Porel、Christopher A. Alabi

  DOI：10.1021/ja507262t

  日期：2014.9.24

  Biological systems have long recognized the importance of macromolecular diversity and have evolved efficient processes for the rapid synthesis of sequence-defined biopolymers. However, achieving sequence control via synthetic methods has proven to be a difficult challenge. Herein we describe efforts to circumvent this difficulty via the use of orthogonal allyl acrylamide building blocks and a liquid-phase fluorous support for the de novo design and synthesis of sequence-specific polymers. We demonstrate proof-of-concept via synthesis and characterization of two sequence-isomeric 10-mer polymers. (1)H NMR and LCMS were used to confirm their chemical structure while tandem MS was used to confirm sequence identity. Further validation of this methodology was provided via the successful synthesis of a sequence-specific 16-mer polymer incorporating nine different monomers. This strategy thus shows promise as an efficient approach for the assembly of sequence-specific functional polymers.
• SEQUENCE-DEFINED POLYMERS AND METHODS OF MAKING SAME AND USING SAME
  申请人：Cornell University

  公开号：US20200299461A1

  公开（公告）日：2020-09-24

  Methods of making sequence-defined polymers and sequence-defined polymers. The methods are based on the orthogonal reactivity of monomers having at least two different functional groups. The sequence-defined polymers can be used in various applications. For example, the SDPs (e.g., pH sensitive SDPs) are used in cell lysis methods or as molecular vehicles to transport drug cargo into cells.
• Tandem Ring-Closing Metathesis/Isomerization Reactions for the Total Synthesis of Violacein
  作者：Mette T. Petersen、Thomas E. Nielsen

  DOI：10.1021/ol400654r

  日期：2013.4.19

  A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.