N-(cinnamoyl)-(S)-phenylalaninol | 1280542-65-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-(cinnamoyl)-(S)-phenylalaninol
• 英文别名: (E)-N-[(1S)-1-hydroxymethyl-2-phenylethyl]-3-phenyl-2-propenamide；(E)-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]-3-phenylprop-2-enamide
• CAS: 1280542-65-5
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: VZKUSXFUBMPSML-FLVLSHQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(cinnamoyl)-(S)-phenylalaninol 在 氯化亚砜 、 potassium carbonate 、 sodium bromide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以60%的产率得到(S,E)-4-benzyl-2-styryl-4,5-dihydrooxazoline
  参考文献：
  名称：

  Practical and efficient synthesis of chiral 2,4-disubstituted oxazolines from β-phosphonoamides

  摘要：

  Herein we report a practical and efficient method for the synthesis of optically active 2,4-disubstituted oxazolines (S)-1a-h in good to excellent yields. The target compounds were prepared in good yield through the Horner-Wadsworth-Emmons reaction of beta-phosphonoamide 3 bearing L-phenylalaninol with commercially available aryl aldehydes followed by the cyclodehydration of the corresponding N-(cinnamoyl)-(S)-phenylalaninol derivatives (S)-2a-h. Additionally, the cyclodehydration of p-phosphonoamide (S)-3 followed by the Horner-Wadsworth-Emmons reaction of p-phosphono-oxazoline (S)-4 with aryl aldehydes also gave the 2,4-disubstituted oxazolines (S)-1a-h. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.003
• 作为产物：
  描述：

  L-苯丙氨醇 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 N-(cinnamoyl)-(S)-phenylalaninol
  参考文献：
  名称：

  Practical and efficient synthesis of chiral 2,4-disubstituted oxazolines from β-phosphonoamides

  摘要：

  Herein we report a practical and efficient method for the synthesis of optically active 2,4-disubstituted oxazolines (S)-1a-h in good to excellent yields. The target compounds were prepared in good yield through the Horner-Wadsworth-Emmons reaction of beta-phosphonoamide 3 bearing L-phenylalaninol with commercially available aryl aldehydes followed by the cyclodehydration of the corresponding N-(cinnamoyl)-(S)-phenylalaninol derivatives (S)-2a-h. Additionally, the cyclodehydration of p-phosphonoamide (S)-3 followed by the Horner-Wadsworth-Emmons reaction of p-phosphono-oxazoline (S)-4 with aryl aldehydes also gave the 2,4-disubstituted oxazolines (S)-1a-h. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.003

文献信息

• Compounds for use in the treatment of aids and other viral diseases and HIV-related infections and compositions containing such compounds, methods of treating such diseases and infections and methods of making such compounds and compositions
  申请人：Kaplan Eliahu

  公开号：US20050239898A1

  公开（公告）日：2005-10-27

  The present invention provides methods for treating Acquired Immunodeficiency Syndrome (AIDS) and other viral diseases and Human Immunodeficiency Virus (HIV) related infections by administering one or more compounds of formula I: wherein: the dotted line represents a single or a double bond; and R 1 and R 2 are the same or different and independently of each other represent —CH 2 OH, —CH 2 OR 4 , —CH(OH)CH 3 , —CH(OR 4 )CH 3 or a group represented by the formula: or salts or hydrates thereof in a carrier which minimizes micellar formation or van der Waals attraction of molecules of said compound. The invention also provides S enantiomeric forms of such compounds which possess the ability to inhibit cell growth whilst being of low toxicity to such cells and methods of making such compounds.

  本发明提供了通过施用一种或多种式 I 的化合物来治疗获得性免疫缺陷综合征（AIDS）和其他病毒性疾病以及与人类免疫缺陷病毒（HIV）相关的感染的方法： 其中： 虚线代表单键或双键；以及 R 1 和 R 2 相同或不同，且各自代表 -CH 2 OH、-CH 2 或 4 , -CH(OH)CH 3 , -CH(OR 4 ) CH 3 或由式 或其盐或水合物在载体中，该载体可最大限度地减少所述化合物分子的胶束形成或范德华吸引力。本发明还提供了这类化合物的 S 对映体形式，它具有抑制细胞生长的能力，同时对这些细胞毒性低，本发明还提供了制造这类化合物的方法。
• Metal-free oxidative amide formation with N-hydroxysuccinimide and hypervalent iodine reagents
  作者：Haoyi Yao、Yun Tang、Kana Yamamoto

  DOI：10.1016/j.tetlet.2012.07.024

  日期：2012.9

  An oxidative amide formation using N-hydroxysuccinimide and hypervalent iodine reagents was developed. The method enables a wide range of aldehydes and amines to be coupled under mild reaction conditions providing amide in good to excellent yield. The radical species in the reaction mixture was observed for the first time using ESR measurement, and along with other mechanistic investigations, a plausible mechanism of the reaction was proposed. Published by Elsevier Ltd.
• COMPOUNDS FOR USE IN THE TREATMENT OF AUTOIMMUNE DISEASES, IMMUNO-ALLERGICAL DISEASES AND ORGAN OR TISSUE TRANSPLANTATION REJECTION
  申请人：Novaremed Ltd.

  公开号：EP1546088B1

  公开（公告）日：2014-12-17
• COMPOUNDS FOR TREATMENT OF AIDS AND OTHER DISEASES
  申请人：Novaremed Ltd.

  公开号：EP1750691B1

  公开（公告）日：2016-08-10
• US7674829B2
  申请人：——

  公开号：US7674829B2

  公开（公告）日：2010-03-09