(S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenyl-hex-4-en-3-one | 220887-32-1

• 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: (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenyl-hex-4-en-3-one
• 英文别名: (5S)-2-Amino-5-(N,N-dibenzylamino)-4-oxo-1,6-diphenylhex-2-ene；(s,z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one；(Z,2S)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one
• CAS: 220887-32-1
• 化学式: C₃₂H₃₂N₂O
• 分子量: 460.619
• InChiKey: IVYLNCUETJNNJU-AYRMWSDDSA-N

物化性质

• 沸点：
  626.2±55.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenyl-hex-4-en-3-one 在 sodium tetrahydroborate 、 甲烷磺酸 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 生成 2-amino-5S-dibenzylamino-4-oxo-1,6-diphenylhexane
  参考文献：
  名称：

  An Efficient Stereocontrolled Strategy for the Synthesis of Hydroxyethylene Dipeptide Isosteres

  摘要：

  A novel and practical synthesis of hydroxyethylene dipeptide isostere 9 from L-phenylalanine via the formation and stereospecific reduction of an enaminone is described.

  DOI：

  10.1021/jo00094a006
• 作为产物：
  描述：

  N,N-二苄基-L-苯丙氨酸苄酯 在 sodium amide 作用下， 生成 (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenyl-hex-4-en-3-one
  参考文献：
  名称：

  Novel lopinavir analogues incorporating non-Aromatic P-1 side chains—Synthesis and structure–Activity relationships

  摘要：

  The HIV protease inhibitor Lopinavir has a pseudosymmetric core unit incorporating benzyl groups at both P-1, P-1' positions. A series of analogues incorporating non-aromatic side chains at the P-1 position were synthesized and the structure-activity relationships explored. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00643-1

文献信息

• Retroviral protease inhibiting compounds
  申请人：Abbott Laboratories

  公开号：EP1170289A2

  公开（公告）日：2002-01-09

  A compound comprising a substituent of the formula (II) is disclosed as an HIV protease inhibitor. Intermediates for making such compounds and processes for making such intermediates are also disclosed.

  披露了一种包含公式（II）取代基的化合物，作为一种HIV蛋白酶抑制剂。还披露了用于制造此类化合物的中间体以及制造此类中间体的过程。
• Pharmaceutical composition
  申请人：Abbott Laboratories

  公开号：US05559158A1

  公开（公告）日：1996-09-24

  A solid pharmaceutical composition is disclosed which comprises a pharmaceutically acceptable adsorbent or a mixture of pharmaceutically acceptable adsorbents to which is adsorbed a mixture of (1) a pharmaceutically acceptable organic solvent or a mixture of pharmaceutically acceptable organic solvents, (2) an HIV protease inhibiting compound and (3) one or more pharmaceutically acceptable acids. The solid composition can optionally be encapsulated in a hard gelatin capsule.

  揭示了一种固体药物组合物，包括一种药学上可接受的吸附剂或一种药学上可接受的吸附剂混合物，该吸附剂或吸附剂混合物吸附了（1）一种药学上可接受的有机溶剂或一种药学上可接受的有机溶剂混合物，（2）一种HIV蛋白酶抑制化合物和（3）一种或多种药学上可接受的酸。该固体组合物可以选择性地封装在硬明胶胶囊中。
• Pharmaceutical composition for inhibiting HIV protease
  申请人：Abbott Laboratories

  公开号：US05484801A1

  公开（公告）日：1996-01-16

  A pharmaceutical composition is disclosed which comprises a solution of an HIV protease inhibiting compound in a pharmaceutically acceptable organic solvent comprising a mixture of (1) (a) a solvent selected from propylene glycol and polyethylene glycol or (b) a solvent selected from polyoxyethyleneglycerol triricinoleate, polyethylene glycol 40 hydrogenated castor oil, fractionated coconut oil, polyoxyethylene (20) sorbitan monooleate and 2-(2-ethoxyethoxy)ethanol or (c) a mixture thereof and (2) ethanol or propylene glycol.

  一种药物组合物被披露，其包括一种HIV蛋白酶抑制化合物的溶液，所述溶液在一种药用可接受的有机溶剂中，所述有机溶剂包括以下混合物：(1) (a) 从丙二醇和聚乙二醇中选择的溶剂，或者 (b) 从聚氧乙烯甘油三蓖麻油酸酯、聚乙二醇40氢化蓖麻油、分馏椰子油、聚氧乙烯(20)山梨醇单油酸酯和2-(2-乙氧基乙氧基)乙醇中选择的溶剂，或者 (c) 其混合物，以及 (2) 乙醇或丙二醇。
• Process for the preparation of a substituted 2,5-diamino-3-hydroxyhexane
  申请人：Abbott Laboratories

  公开号：US05491253A1

  公开（公告）日：1996-02-13

  Intermediates and processes are disclosed which are useful for the preparation of a substantially pure compound of the formula: ##STR1## wherein R.sub.6 and R.sub.7 are each hydrogen or R.sub.6 and R.sub.7 are independently selected from ##STR2## wherein R.sub.a and R.sub.b are independently selected from hydrogen, loweralkyl and phenyl and R.sub.c, R.sub.d and R.sub.e are independently selected from hydrogen, loweralkyl, trifluoromethyl, alkoxy, halo and phenyl; and ##STR3## wherein the naphthyl ring is unsubstituted or substituted with one, two or three substitutents independently selected from loweralkyl, trifluoromethyl, alkoxy and halo; or R.sub.6 is as defined above and R.sub.7 is R.sub.7a OC(O)--wherein R.sub.7a is loweralkyl or benzyl; or R.sub.6 and R.sub.7 taken together with the nitrogen atom to which they are bonded are ##STR4## wherein R.sub.f, R.sub.g, R.sub.h and R.sub.i are independently selected from hydrogen, loweralkyl, alkoxy, halogen and trifluoromethyl and R.sub.8 is hydrogen or --C(O)R" wherein R" is loweralkyl, alkoxy, benzyloxy or phenyl wherein the phenyl ring is unsubstituted or substituted with one, two or three substituents independently selected from loweralkyl, trifluoromethyl, alkoxy and halo; or an acid addition salt thereof.

  揭示了用于制备公式的基本纯化合物的中间体和过程：其中R.sub.6和R.sub.7分别为氢或R.sub.6和R.sub.7分别选择自##其中R.sub.a和R.sub.b分别选择自氢、较低烷基和苯基，R.sub.c、R.sub.d和R.sub.e分别选择自氢、较低烷基、三氟甲基、烷氧基、卤素和苯基；和##其中萘环未取代或取代一个、两个或三个从较低烷基、三氟甲基、烷氧基和卤素中独立选择的取代基；或R.sub.6如上定义，而R.sub.7为R.sub.7a OC(O)--其中R.sub.7a为较低烷基或苄基；或R.sub.6和R.sub.7与它们结合的氮原子一起为##其中R.sub.f、R.sub.g、R.sub.h和R.sub.i分别选择自氢、较低烷基、烷氧基、卤素和三氟甲基，R.sub.8为氢或--C(O)R"其中R"为较低烷基、烷氧基、苄氧基或苯基，苯环未取代或取代一个、两个或三个从较低烷基、三氟甲基、烷氧基和卤素中独立选择的取代基；或其酸加盐。
• 一种合成利托那韦中间体的方法
  申请人：中国科学院新疆生态与地理研究所

  公开号：CN106380412A

  公开（公告）日：2017-02-08

  本发明涉及一种合成利托那韦中间体的方法，该方法所述的中间体为(S,Z)‑5‑氨基‑2‑(二苄基氨基)‑1,6‑二苯基己‑4‑烯‑3‑酮，采用将L‑苯丙氨酸，水，氢氧化钠混合，加入氯化苄，加入庚烷，用甲醇水溶液洗涤，减压蒸干得到黄色油状物2‑二苄胺基‑3‑苯基丙酸苄酯；在氮气保护下溶于甲基叔丁基醚，在低温条件下与无水乙腈反应，加入氢化钠搅拌，再缓慢滴加格氏试剂，降温，加入无水甲醇水解多余的氨基钠，静置分层，用甲基叔丁基醚提取水层，合并油层浓缩，蒸干得到油状物后，加无水乙醇，过滤，真空干燥，得到白色粉末利托那韦中间体(S,Z)‑5‑氨基‑2‑(二苄基氨基)‑1,6‑二苯基己‑4‑烯‑3‑酮。本发明所述方法与传统工艺相比，简化反应步骤，降低反应成本，减少有毒试剂的使用。