(R)-3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (S)-1,5-dimethylhex-4-enyl ester | 60609-59-8

• 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: (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (S)-1,5-dimethylhex-4-enyl ester
• 英文别名: (S)-sulcatol (R)-mosher ester；[(2S)-6-methylhept-5-en-2-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 60609-59-8
• 化学式: C₁₈H₂₃F₃O₃
• 分子量: 344.374
• InChiKey: YVKWFCGFICHGBO-WMLDXEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L(-)岩藻糖 在 吡啶 作用下， 生成 (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (S)-1,5-dimethylhex-4-enyl ester
  参考文献：
  名称：

  Synthesis of enantiomers of sulcatol

  摘要：

  报道了从商业可获得的碳水化合物前体合成R-(−)-和S-(+)-6-甲基庚-5-烯-2-醇（硫醇）。R-(−)对映体的合成利用了2-去氧-D-核糖的四个羟基功能作为手性二级醇中心的预成型前体。L-岩藻糖的五个羟基团提供了类似合成S(+)对映体的基础。这些异构体将用于测试西北美洲木材害虫Gnathotricus sulcatus的聚集反应。

  DOI：

  10.1139/v77-457

文献信息

• ISOMETHEPTENE ISOMER
  申请人：TONIX PHARMACEUTICALS INC.

  公开号：US20140212486A1

  公开（公告）日：2014-07-31

  The invention relates to a purified Isometheptene compound comprising the structure according to Formula (I), or a hydrochloride, or a pharmaceutically acceptable addition salt thereof. In particular, the disclosure relates to the synthesis, purification and characterization of an Isometheptene isomer mucate crystal 2, wherein the Isometheptene isomer 2 is stereochemically characterized as (R)-enantiomer, respectively. The Isometheptene (R)-enantiomer activity indicates a selective centrally acting selective ligand for Imidazoline subtype 1 (I1) receptor sites; and more specifically, the disclosure provides an antihypertensive composition for treatment of migraine and other neurovascular or neurogenic pain from abdominal distress. (R)-Isometheptene enantiomer or isomer 2 may be an anti-hypertensive agent with lower side effects than the racemate form. Therefore (R)-Isometheptene is believed to be effective against episodic tension-type headaches (ETTH). The (R)-Isometheptene enantiomer or isomer 2 is believed to effectively lower blood pressure, used alone or together with other headache ameliorating drugs. Methods of synthesis and treatment are described. Regarding (R)-Isometheptene crystals data of X-ray crystallography are presented.

  该发明涉及一种纯化的异甲苯丙胺化合物，其结构符合式(I)，或其盐酸盐，或其药用上可接受的加合物。具体而言，该公开涉及异甲苯丙胺异构体粘酸晶体2的合成、纯化和表征，其中异甲苯丙胺异构体2的立体化学特性为(R)-对映体。异甲苯丙胺(R)-对映体活性表明其为咪唑啉亚型1(I1)受体位点的选择性中枢作用选择性配体；更具体地，该公开提供了一种用于治疗偏头痛和其他源自腹部不适的神经血管性或神经源性疼痛的降压组合物。异甲苯丙胺(R)-对映体或异构体2可能是一种抗高血压药物，其副作用较盐酸异甲苯丙胺的形式更少。因此，人们认为异甲苯丙胺(R)对映体对阵发性张力型头痛(ETTH)有效。异甲苯丙胺(R)对映体或异构体2被认为能有效降低血压，可单独使用或与其他缓解头痛药物一起使用。描述了合成和治疗方法。关于异甲苯丙胺(R)晶体的X射线衍射数据已被提供。
• US9403755B2
  申请人：——

  公开号：US9403755B2

  公开（公告）日：2016-08-02
• [EN] ISOMETHEPTENE ISOMER<br/>[FR] ISOMÈRE DE L'ISOMÉTHEPTÈNE
  申请人：TONIX PHARMACEUTICALS INC

  公开号：WO2014113734A2

  公开（公告）日：2014-07-24

  The invention relates to a purified Isometheptene compound comprising the structure according to Formula (I), (Formula (I)) or a hydrochloride, or a pharmaceutically acceptable addition salt thereof. In particular, the disclosure relates to the synthesis, purification and characterization of an Isometheptene isomer mucate crystal 2, wherein the Isometheptene isomer 2 is stereochemically characterized as (R)-enantiomer, respectively. The Isometheptene (R)-enantiomer activity indicates a selective centrally acting selective ligand for Imidazoline subtype 1 (I1) receptor sites; and more specifically, the disclosure provides an antihypertensive composition for treatment of migraine and other neurovascular or neurogenic pain from abdominal distress. (R)-Isometheptene enantiomer or isomer 2 may be an anti-hypertensive agent with lower side effects than the racemate form. Therefore (R)-Isometheptene is believed to be effective against episodic tension-type headaches (ETTH). The (R)-Isometheptene enantiomer or isomer 2 is believed to effectively lower blood pressure, used alone or together with other headache ameliorating drugs. Methods of synthesis and treatment are described. Regarding (R)- Isometheptene crystals data of X-ray crystallography are presented.
• Synthesis of enantiomers of sulcatol
  作者：Hermann R. Schuler、Keith N. Slessor

  DOI：10.1139/v77-457

  日期：1977.9.15

  The synthesis of R-(−)- and S-(+)-6-methylhept-5-en-2-ol (sulcatol) is reported from commercially available carbohydrate precursors. The synthesis of the R-(−) enantiomer utilizes the four hydroxy function of 2-deoxy-D-ribose as a preformed precursor of the chiral secondary alcohol centre. The five hydroxy group of L-fucose provides the basis for a similar synthesis of the S(+) enantiomer. These isomers are to be used to test the aggregation response of Gnathotricus sulcatus, a northwestern American timber pest.

  报道了从商业可获得的碳水化合物前体合成R-(−)-和S-(+)-6-甲基庚-5-烯-2-醇（硫醇）。R-(−)对映体的合成利用了2-去氧-D-核糖的四个羟基功能作为手性二级醇中心的预成型前体。L-岩藻糖的五个羟基团提供了类似合成S(+)对映体的基础。这些异构体将用于测试西北美洲木材害虫Gnathotricus sulcatus的聚集反应。