N-[1-(2-phenylethyl)prop-2-enyl]benzamide

• 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-[1-(2-phenylethyl)prop-2-enyl]benzamide
• 英文别名: N-(5-phenylpent-1-en-3-yl)-benzamide；N-(5-phenylpent-1-en-3-yl)benzamide
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: IHTPCZPNBWDDIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-[1-(2-phenylethyl)prop-2-enyl]benzamide 在 sodium periodate 、 ruthenium(III) trichloride hydrate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 生成 (S)-2-benzoylamino-4-phenylbutyric acid 、 (R)-2-benzamido-4-phenylbutanoic acid
  参考文献：
  名称：

  Asymmetric synthesis of α- and β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines

  摘要：

  The diastereoselective addition of triorganozincates to (R)-N-(tert-butanesulfinyl)imines has been used as a key step to achieve the synthesis of highly enantiomerically enriched N-protected alpha- and beta-amino acids. Desulfinylation of the addition products followed by benzoylation of the nitrogen atom of the obtained primary amines and oxidation of one of the substituents on the carbon atom connected to the nitrogen complete the sequence. Using the same configuration in the sulfinyl chiral auxiliary, alpha-amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. alpha,alpha-Disubstituted alpha-amino esters with high enantiomeric purity can also be prepared when a-imino esters are the starting substrates. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.046
• 作为产物：
  描述：

  5-phenylpent-1-en-3-ol 、 苯甲酰氯 在 5-(dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl)-5H-dibenzo[b,f]azepine 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 氨基磺酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.25h， 以73%的产率得到N-[1-(2-phenylethyl)prop-2-enyl]benzamide
  参考文献：
  名称：

  PHOSPHORAMIDITE LIGAND AND PRODUCTION METHOD OF ALLYLIC AMINE USING THE SAME

  摘要：

  本发明提供了一种制备烯丙胺的生产方法，烯丙胺的化学式为(III)，其中R3如规范中定义，该方法包括使用磷酰胺配体(I)和铱配合物，在磺酸的存在下，将烯丙醇(II)与磺酸反应。根据本发明，可以直接从烯丙醇中生产出主要的烯丙胺，而无需使用烯丙醇的活化剂，也无需将烯丙醇转化为其活化化合物。

  公开号：

  US20090054689A1

文献信息

• Phosphoramidite ligand and production method of allylic amine using the same
  申请人：Sumitomo Chemical Company, Limited

  公开号：US07863443B2

  公开（公告）日：2011-01-04

  The present invention provides a production method of an allylic amine represented by the formula (III): wherein R3 is as defined in the specification, which comprises reacting by an allylic alcohol represented by the formula (II): wherein R3 is as defined in the specification, with sulfamic acid, in the presence of a phosphoramidite ligand represented by the formula (I): wherein each symbol is as defined in the specification, and an iridium complex. According to the present invention, a primary allylic amine can be produced directly from an allylic alcohol, without use of an activator for an allylic alcohol and conversion of an allylic alcohol into an activated compound thereof.

  本发明提供了一种联烯胺的生产方法，其化学式为(III)，其中R3如规范中所定义，包括以下步骤：将化学式为(II)的联烯醇与磺酸在磷酰胺配体和铱配合物的存在下反应，其中R3如规范中所定义。根据本发明，可以直接从联烯醇中生产出主要的联烯胺，而无需使用联烯醇的活化剂，并将联烯醇转化为其活化化合物。
• Iridium-Catalyzed Synthesis of Primary Allylic Amines from Allylic Alcohols: Sulfamic Acid as Ammonia Equivalent
  作者：Christian Defieber、Martin A. Ariger、Patricia Moriel、Erick M. Carreira

  DOI：10.1002/anie.200700159

  日期：2007.4.20
• US7863443B2
  申请人：——

  公开号：US7863443B2

  公开（公告）日：2011-01-04
• Asymmetric synthesis of α- and β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines
  作者：Raquel Almansa、Juan F. Collados、David Guijarro、Miguel Yus

  DOI：10.1016/j.tetasy.2010.03.046

  日期：2010.6

  The diastereoselective addition of triorganozincates to (R)-N-(tert-butanesulfinyl)imines has been used as a key step to achieve the synthesis of highly enantiomerically enriched N-protected alpha- and beta-amino acids. Desulfinylation of the addition products followed by benzoylation of the nitrogen atom of the obtained primary amines and oxidation of one of the substituents on the carbon atom connected to the nitrogen complete the sequence. Using the same configuration in the sulfinyl chiral auxiliary, alpha-amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. alpha,alpha-Disubstituted alpha-amino esters with high enantiomeric purity can also be prepared when a-imino esters are the starting substrates. (C) 2010 Elsevier Ltd. All rights reserved.
• PHOSPHORAMIDITE LIGAND AND PRODUCTION METHOD OF ALLYLIC AMINE USING THE SAME
  申请人：CARREIRA Erick M.

  公开号：US20090054689A1

  公开（公告）日：2009-02-26

  The present invention provides a production method of an allylic amine represented by the formula (III): wherein R 3 is as defined in the specification, which comprises reacting by an allylic alcohol represented by the formula (II): wherein R 3 is as defined in the specification, with sulfamic acid, in the presence of a phosphoramidite ligand represented by the formula (I): wherein each symbol is as defined in the specification, and an iridium complex. According to the present invention, a primary allylic amine can be produced directly from an allylic alcohol, without use of an activator for an allylic alcohol and conversion of an allylic alcohol into an activated compound thereof.

  本发明提供了一种制备烯丙胺的生产方法，烯丙胺的化学式为(III)，其中R3如规范中定义，该方法包括使用磷酰胺配体(I)和铱配合物，在磺酸的存在下，将烯丙醇(II)与磺酸反应。根据本发明，可以直接从烯丙醇中生产出主要的烯丙胺，而无需使用烯丙醇的活化剂，也无需将烯丙醇转化为其活化化合物。