(1S)-cyclohex-3-enecarboxylic acid 2,2,2-trifluoro-ethyl ester | 891862-16-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S)-cyclohex-3-enecarboxylic acid 2,2,2-trifluoro-ethyl ester
• 英文别名: (S)-2,2,2-trifluoroethyl cyclohex-3-enecarboxylate；3-Cyclohexene-1-carboxylic acid, 2,2,2-trifluoroethyl ester, (1S)-；2,2,2-trifluoroethyl (1S)-cyclohex-3-ene-1-carboxylate
• CAS: 891862-16-1
• 化学式: C₉H₁₁F₃O₂
• 分子量: 208.18
• InChiKey: FWRKUOVBXXYWPW-SSDOTTSWSA-N

物化性质

• 沸点：
  185.2±40.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S)-cyclohex-3-enecarboxylic acid 2,2,2-trifluoro-ethyl ester 在 ammonium hydroxide 、 lithium aluminium tetrahydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 为溶剂， 反应 9.0h， 生成 ethyl (cyclohex-3-enylmethyl)carbamate
  参考文献：
  名称：

  Development of a Scalable Synthesis of a Pyridinyl-3-azabicyclononene, a Novel Nicotinic Partial Agonist

  摘要：

  The process research and development of two syntheses of a novel nicotinic partial agonist, TC-8817 ((+)-5), are described. The original Medicinal Chemistry route had multiple flaws, making it unsuitable for further development. A second approach was explored which was more amenable to optimization. The key steps were an intramolecular Lewis acid-promoted cyclization, a dibromination/elimination sequence to provide a vinyl bromide, and subsequent Suzuki coupling with 3-pyridineboronic acid. The overall yield of similar to 3-16% over nine steps was offset by the low cost of goods and ease of synthesis. A major drawback was the need for simulated moving bed chiral separation on the penultimate intermediate to afford the subsequently desired single enantiomer version. A third-generation, asymmetric variation afforded a key intermediate in good yield and enantiomeric purity, providing proof of concept for a more efficient production of the desired (+)-enantiomer.

  DOI：

  10.1021/op400002r
• 作为产物：
  描述：

  丙烯酸三氟乙酯 、 1,3-丁二烯 在 chiral oxazaborolidinium trifluoromethanesulfonimide salt 作用下， 反应 30.0h， 以97%的产率得到(1S)-cyclohex-3-enecarboxylic acid 2,2,2-trifluoro-ethyl ester
  参考文献：
  名称：

  A Short Enantioselective Pathway for the Synthesis of the Anti-Influenza Neuramidase Inhibitor Oseltamivir from 1,3-Butadiene and Acrylic Acid

  摘要：

  A short synthetic pathway has been developed for the synthesis of oseltamivir (1) or the enantiomer (ent-1). The intermediates and conditions for this process are summarized in Scheme 1. The synthesis provides a number of advantages: (1) use of inexpensive and abundant starting materials; (2) complete enantio-, regio-, and diastereocontrol; (3) avoidance of explosive, azide-type intermediates; (4) good overall yield (ca. 30%, still not completely optimized); and (5) scalability.

  DOI：

  10.1021/ja0616433

文献信息

• PROCESS FOR THE PREPARATION OF OSELTAMIVIR AND METHYL 3-EPI-SHIKIMATE
  申请人：Council of Scientific & Industrial Research

  公开号：US20140243537A1

  公开（公告）日：2014-08-28

  The present invention discloses high yielding enantioselective process for synthesis of Oseltamivir from readily available starting material, cis-1,4-butene diol. The process features incorporation of chirality using sharpless asymmetric epoxidation (AE) and diastereoselective Barbier allylation and construction of cyclohexene carboxylic acid ester core through a ring closing metathesis (RCM) reaction. Further also disclosed herein is synthesis of (−)-methyl 3-epi-shikimate.

  本发明揭示了一种高产高对映选择性的奥司他韦合成工艺，从易得的起始物质顺式-1,4-丁二醇出发。该工艺采用Sharpless不对称环氧化（AE）和立体选择性的Barbier烯丙基化，通过环内酯交换反应（RCM）构建环己烯羧酸酯核心以引入手性。此外，还揭示了(−)-甲基3-epi-香椿糖酸的合成。
• INTERMEDIATE COMPOUNDS OF TAMIFLU, METHODS OF PREPARATION AND USES THEREOF
  申请人：Ma Dawei

  公开号：US20140221662A1

  公开（公告）日：2014-08-07

  Chiral amino compounds, methods of preparation and uses thereof. Tamiflu can be obtained from the said compounds. Multi-substituted chiral tetrahydropyrrolyl amine which can be used as intermediate compounds of medicament can also be produced by the said compounds.

  手性氨基化合物，其制备方法及用途。 好病毒药物达菌素可以从这些化合物中获得。 这些化合物还可以制备用作药物中间体的多取代手性四氢吡咯基胺。
• Triflimide Activation of a Chiral Oxazaborolidine Leads to a More General Catalytic System for Enantioselective Diels−Alder Addition
  作者：Do Hyun Ryu、E. J. Corey

  DOI：10.1021/ja035393r

  日期：2003.5.1

  The strong acid triflimide ((CF3SO2)2NH) protonates chiral oxazaborolidines to form superactive, stable, chiral Lewis acids which are highly effective catalysts for a wide variety of enantioselective Diels-Alder reactions, documented herein by more than 20 examples.
• US9040738B2
  申请人：——

  公开号：US9040738B2

  公开（公告）日：2015-05-26
• US9150498B2
  申请人：——

  公开号：US9150498B2

  公开（公告）日：2015-10-06