(E)-methyl cinnamyl(naphthalen-1-ylmethyl)carbamate | 1334031-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-methyl cinnamyl(naphthalen-1-ylmethyl)carbamate
• 英文别名: methyl cinnamyl(naphthalen-1-ylmethyl)carbamate；methyl N-(naphthalen-1-ylmethyl)-N-[(E)-3-phenylprop-2-enyl]carbamate
• CAS: 1334031-95-6
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: KXPQOIDMVITFNU-DHZHZOJOSA-N

物化性质

• 沸点：
  515.1±40.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-methyl cinnamyl(naphthalen-1-ylmethyl)carbamate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以87%的产率得到萘替芬
  参考文献：
  名称：

  Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines

  摘要：

  The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the carbonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.

  DOI：

  10.1021/jo201105z
• 作为产物：
  描述：

  (氯甲基)萘 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium acetate 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醚 、 水 、 苯甲腈 为溶剂， 反应 25.5h， 生成 (E)-methyl cinnamyl(naphthalen-1-ylmethyl)carbamate
  参考文献：
  名称：

  Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines

  摘要：

  The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the carbonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.

  DOI：

  10.1021/jo201105z

文献信息

• One-Pot Synthesis of Allylamine Derivatives by Iodine- Catalyzed Three-Component Reaction of N-Heterocycles, Paraformaldehyde and Styrenes
  作者：Zheng-Jun Quan、Wang-Hua Hu、Zhang Zhang、Yu-Xia Da、Xiao-Dong Jia、Xi-Cun Wang

  DOI：10.1002/adsc.201201097

  日期：2013.3.25

  The molecular iodine‐catalyzed three‐component reaction of amides or amide derivatives, paraformaldehyde and styrenes allows for the clean generation of allylamine derivatives in good yields and high regioselectivities. The reaction, forming water as the sole co‐product, is an experimentally easy to conduct transformation in the absence of transition metals under mild conditions.

  酰胺或酰胺衍生物，多聚甲醛和苯乙烯的分子碘催化三组分反应可实现高收率和高区域选择性的烯丙基胺衍生物的清洁生成。该反应形成水是唯一的副产物，在温和条件下，在没有过渡金属的情况下，该实验很容易进行转化。