2-[4-(1E)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-1-propen-1yl]phenyl-4,4-dimethyl-2-oxazoline | 71441-33-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-[4-(1E)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-1-propen-1yl]phenyl-4,4-dimethyl-2-oxazoline
• 英文别名: 2-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]-phenyl]-4,4-dimethyl-2-oxazoline；4,4-dimethyl-2-[4-[(E)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-enyl]phenyl]-5H-1,3-oxazole
• CAS: 71441-33-3
• 化学式: C₂₈H₃₅NO
• 分子量: 401.592
• InChiKey: NFGLQRKBYMMHHQ-KNTRCKAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[4-(1E)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-1-propen-1yl]phenyl-4,4-dimethyl-2-oxazoline 在 盐酸 、 水 作用下， 反应 3.0h， 以85%的产率得到芳维甲酸
  参考文献：
  名称：

  Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor

  摘要：

  An efficient and novel total synthesis of the two bioactive retinoids temarotene and arotinoid acid (TTNPB) is described. The key steps in this process include the regio and stereoselective hydrotelluration of thioacetylene 9 and Te/Li transmetalation of mixed (Z)-1,2-bis(organylchalcogene)-1-alkene (Z)-3. The subsequent reaction involving the beta-phenylthio vinyl lithiated intermediate 10 with dimethyl sulfate gave the (E)-vinyl sulfide 11. The Ni+2 cross-coupling of 11 with the corresponding phenylzinc bromide and p-oxazoline phenylzinc bromide 12 afforded the respective temarotene 2 and retinoid-oxazoline substituted 13. Finally, compound 13 was deprotected with HCl to furnish arotinoid acid (TTNPB) 1. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.092
• 作为产物：
  描述：

  2,5-二氯-2,5-二甲基己烷 在 aluminum (III) chloride 、 copper(l) iodide 、 正丁基锂 、 1,2-双(二苯基膦)乙烷氯化镍 、 sodium hydride 、 三乙胺 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.84h， 生成 2-[4-(1E)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-1-propen-1yl]phenyl-4,4-dimethyl-2-oxazoline
  参考文献：
  名称：

  Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor

  摘要：

  An efficient and novel total synthesis of the two bioactive retinoids temarotene and arotinoid acid (TTNPB) is described. The key steps in this process include the regio and stereoselective hydrotelluration of thioacetylene 9 and Te/Li transmetalation of mixed (Z)-1,2-bis(organylchalcogene)-1-alkene (Z)-3. The subsequent reaction involving the beta-phenylthio vinyl lithiated intermediate 10 with dimethyl sulfate gave the (E)-vinyl sulfide 11. The Ni+2 cross-coupling of 11 with the corresponding phenylzinc bromide and p-oxazoline phenylzinc bromide 12 afforded the respective temarotene 2 and retinoid-oxazoline substituted 13. Finally, compound 13 was deprotected with HCl to furnish arotinoid acid (TTNPB) 1. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.092

文献信息

• Method to incorporate N-(4-hydroxyphenyl) retinamide in liposomes
  申请人：Board of Regents, The University of Texas System

  公开号：US20020143062A1

  公开（公告）日：2002-10-03

  Disclosed herein are simple and unique methods of methods of preparing liposomal compositions of N-(4-hydroxyphenyl) retinamide (4HPR) and/or other retinoids. Also disclosed are liposomal 4HPR compositions prepared by such methods, and use of such compositions in the treatment of diseases, such as breast cancer. This invention further provides methods for improving the efficacy of N-(4-hydroxyphenyl) retinamide (4HPR) as a chemopreventive agent in the presence of agents that potentiates its ability increase the expression of inducible nitric oxide synthase (iNOS, and NO production in cells.

  本文披露了制备N-(4-羟基苯基)视黄酰胺（4HPR）和/或其他视黄醇脂质体组合物的简单且独特的方法。还披露了通过这些方法制备的脂质体4HPR组合物，并将这种组合物用于治疗疾病，如乳腺癌。本发明还提供了一种方法，通过增强诱导型一氧化氮合酶（iNOS）和细胞内NO产生的能力，提高N-(4-羟基苯基)视黄酰胺（4HPR）作为化学预防剂的功效。
• Stilbenderivate, ihre Herstellung und Arzneimittel enthaltend diese Stilbenderivate
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0002742B1

  公开（公告）日：1982-04-14
• A METHOD TO INCORPORATE N-(4-HYDROXYPHENYL) RETINAMIDE IN LIPOSOMES
  申请人：Board of Regents, The University of Texas System

  公开号：EP1328262A2

  公开（公告）日：2003-07-23
• US4326055A
  申请人：——

  公开号：US4326055A

  公开（公告）日：1982-04-20
• [EN] A METHOD TO INCORPORATE N-(4-HYDROXYPHENYL) RETINAMIDE IN LIPOSOMES<br/>[FR] PROCEDE SERVANT A INCORPORER DU N-(4-HYDROXYPHENYL) RETINAMIDE DANS DES LIPOSOMES
  申请人：UNIV TEXAS

  公开号：WO2002032413A2

  公开（公告）日：2002-04-25

  Disclosed herein are simple and unique methods of methods of preparing liposomal compositions of N-(4-hydroxyphenyl) retinamide (4HPR) and/or other retinoids. Also disclosed are liposomal 4HPR compositions prepared by such methods and use of such compositions in the treatment of diseases, such as breast cancer. This invention further provides methods for improving the efficacy of N-(4-hydroxyphenyl) retinamide (4HPR) as a chemopreventive agent in the presence of agents that potentiates its ability increase the expression of inducible nitric oxide synthase (iNOS), and NO production in cells.