N,N-bis(3-phenylprop-2-enyl)acetamide | 692263-13-1

• 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,N-bis(3-phenylprop-2-enyl)acetamide
• CAS: 692263-13-1
• 化学式: C₂₀H₂₁NO
• 分子量: 291.393
• InChiKey: COFIJFZJPJQIAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  482.9±45.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N,N-bis(3-phenylprop-2-enyl)acetamide 在 aluminum (III) chloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 lithium aluminium tetrahydride 、 氢气 、 sodium acetate 作用下， 以 四氢呋喃 、 苯甲腈 为溶剂， 反应 13.5h， 生成 阿尔维林
  参考文献：
  名称：

  Construction of 3-arylpropylamines using Heck arylations. The total synthesis of cinacalcet hydrochloride, alverine, and tolpropamine

  摘要：

  New synthetic routes toward the commercial drugs cinacalcet hydrochloride, alverine, and tolpropamine were developed using a Heck-Matsuda arylation as the key-step. Several reaction conditions were evaluated for the Heck-Matsuda reaction using allylamine derivatives and arenediazonium salts. For cinacalcet hydrochloride, N-formylamide provided the best result, furnishing the synthetic target in a very high overall yield (75% over five steps). For alverine, the best results were obtained using a double Heck-Matsuda strategy, providing alverine in an excellent overall yield (69%) from N-acetyl diallylamine in three steps. Tolpropamine was synthesized in a 46% yield over five steps using an efficient reductive Heck-Matsuda arylation between p-bromo-methylcinnamate with 3-chloro tolyldiazonium salt, generating the beta,beta-diaryl propionate that was converted to tolpropamine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.014
• 作为产物：
  描述：

  N,N-diallylacetamide 、 benzenediazonium tetrafluoroborate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium acetate 作用下， 以 苯甲腈 为溶剂， 以85%的产率得到N,N-bis(3-phenylprop-2-enyl)acetamide
  参考文献：
  名称：

  Construction of 3-arylpropylamines using Heck arylations. The total synthesis of cinacalcet hydrochloride, alverine, and tolpropamine

  摘要：

  New synthetic routes toward the commercial drugs cinacalcet hydrochloride, alverine, and tolpropamine were developed using a Heck-Matsuda arylation as the key-step. Several reaction conditions were evaluated for the Heck-Matsuda reaction using allylamine derivatives and arenediazonium salts. For cinacalcet hydrochloride, N-formylamide provided the best result, furnishing the synthetic target in a very high overall yield (75% over five steps). For alverine, the best results were obtained using a double Heck-Matsuda strategy, providing alverine in an excellent overall yield (69%) from N-acetyl diallylamine in three steps. Tolpropamine was synthesized in a 46% yield over five steps using an efficient reductive Heck-Matsuda arylation between p-bromo-methylcinnamate with 3-chloro tolyldiazonium salt, generating the beta,beta-diaryl propionate that was converted to tolpropamine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.014

文献信息

• Visible Light [2+2] Photocycloaddition Mediated by Flavin Derivative Immobilized on Mesoporous Silica
  作者：Jessica Špačková、Eva Svobodová、Tomáš Hartman、Ivan Stibor、Jitka Kopecká、Jana Cibulková、Josef Chudoba、Radek Cibulka

  DOI：10.1002/cctc.201601654

  日期：2017.4.7

  7,8‐Dimethoxy‐3‐methylalloxazine was immobilized on mesoporous silica (MCM‐41) to provide a heterogenized flavin photocatalyst. Thus, the prepared heterogeneous catalyst 2 was found to sensitize the visible light [2+2] cycloaddition of various types of dienes to produce corresponding cyclobutanes in high yields and diastereoselectivities. Use of 2 enables procedures which are advantageous owing to

  将7,8-二甲氧基-3-甲基别恶嗪固定在介孔二氧化硅（MCM-41）上，以提供异质黄素光催化剂。因此，发现制备的非均相催化剂2使各种类型的二烯的可见光[2 + 2]环加成敏化，以高产率和非对映选择性产生相应的环丁烷。使用2将使程序具有优势，因为其操作和后处理简单，不需要添加剂，并且产生的废物最少。