(+)-BHFF

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (+)-BHFF
• 英文别名: (S)-(-)-5,7-di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one；(S)-5,7-di-tert-butyl-3-hydroxy-3-(trifluoromethyl)benzofuran-2(3H)-one；(S)-BHFF；(3S)-5,7-ditert-butyl-3-oxidanyl-3-(trifluoromethyl)-1-benzofuran-2-one；(3S)-5,7-ditert-butyl-3-hydroxy-3-(trifluoromethyl)-1-benzofuran-2-one
• 化学式: C₁₇H₂₁F₃O₃
• 分子量: 330.347
• InChiKey: RVNOANDLZIIFHB-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4-二叔丁基苯酚 、 3,3,3-三氟丙酮酸乙酯 在 copper(II) bis(trifluoromethanesulfonate) 、 (3aS,3a'S,8aR,8a'R)-2,2'-(propane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以94%的产率得到(+)-BHFF
  参考文献：
  名称：

  串联Friedel-Crafts /内酯化反应催化不对称合成3-羟基-3-三氟甲基苯并呋喃酮

  摘要：

  据报道，具有高度对映选择性和区域选择性的手性路易斯酸催化串联Friedel-Crafts /内酯化反应，可直接获得大量3-羟基-3-三氟甲基苯并呋喃-2-酮，产率高达94％，ee高达99％以上。 。机理研究表明，酚羟基与三氟丙酮酸之间的相互作用是高对映选择性和区域选择性的最可能的因素。可以使用0.05 mol％的催化剂以克为单位获得光学纯的（-）-BHFF，这证明了该方法在药物化学中的潜在用途。

  DOI：

  10.1021/acs.orglett.5b02440

文献信息

• 2-phenyl-3,3,3-trifluoro-2-hydroxy-propionic acid derivatives
  申请人：Malherbe Parichehr

  公开号：US20070027204A1

  公开（公告）日：2007-02-01

  The present invention relates to compounds of formula I: wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined in the specification and claims, which compounds are active on the GABA B receptor and are useful in the control or prevention of CNS illnesses, especially of illnesses and disorders comprising anxiety, depression, epilepsy, schizophrenia, and cognitive disorders.

  本发明涉及以下式I的化合物： 其中R1、R2、R3、R4、R5和R6如规范和声明中定义的那样，这些化合物对GABA B 受体具有活性，并且在控制或预防中枢神经系统疾病，特别是包括焦虑、抑郁症、癫痫、精神分裂症和认知障碍的疾病和疾病中是有用的。
• First asymmetric organocatalyzed domino Friedel–Crafts/lactonization reaction in the enantioselective synthesis of the GABAB receptor modulator (S)-BHFF
  作者：Fabrizio Vetica、Renata Marcia de Figueiredo、Emilia Cupioli、Augusto Gambacorta、M. Antonietta Loreto、Martina Miceli、Tecla Gasperi

  DOI：10.1016/j.tetlet.2016.01.015

  日期：2016.2

  An asymmetric domino Friedel–Crafts/lactonization sequence between phenols and trifluoropyruvate has been accomplished for the first enantioselective synthesis of (S)-BHFF, a positive allosteric modulator (PAM) of GABAB receptor. The developed protocol leads to 3-OH-benzofuranone derivatives bearing a quaternary stereogenic center, and gives a valuable access to bioactive compounds with promising pharmaceutical

  苯酚和三氟丙酮酸酯之间的不对称多米诺夫弗里德尔-克拉夫特/内酯化序列已经完成，用于（S）-BHFF的对映选择性合成，这是一种GABA B受体的正变构调节剂（PAM）。所开发的方案导致3-OH-苯并呋喃酮衍生物带有季立体中心，并为有前途的药物应用提供了生物活性化合物的宝贵途径。
• 2-PHENYL-3,3,3-TRIFLUORO-2-HYDROXY-PROPIONIC ACID DERIVATIVES
  申请人：Malherbe Parichehr

  公开号：US20080234356A1

  公开（公告）日：2008-09-25

  The present invention a method of treating anxiety by administering compounds that are active on the GABA B receptor, having formula I: wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined in the specification and claims.

  本发明提供了一种通过给予对GABAB受体具有活性的化合物治疗焦虑的方法，该化合物具有I式：其中R1、R2、R3、R4、R5和R6如说明书和权利要求所定义。
• 2-HYDROXY-PROPIONIC ACID DERIVATIVES AND 3-HYDROXY-BENZOFURAN-2-ONE DERIVATIVES WITH AFFINITY FOR THE GABA-B-RECEPTOR
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1915357B1

  公开（公告）日：2010-09-08
• COMPOSITIONS AND METHODS FOR TOPICAL TREATMENT OF DERMAL AND OCULAR CONDITIONS
  申请人：GABADERM, INC.

  公开号：US20210038503A1

  公开（公告）日：2021-02-11

  The instant disclosure provides methods and compositions for the treatment of skin disorders associated with itch, irritation, inflammation, and pain, such as psoriasis, eczema, and skin ulcers. The instant disclosure also provides methods and compositions for the treatment of ocular conditions associated with itch, irritation, inflammation, and pain, such as ocular itch, conjunctivitis and eye infections. Generally, compositions include modulator of gamma-amino-butyric-acid (GABA) receptor, such as propofol. The concentration of the GABA modulator in the composition is typically sufficiently high so as to activate GABA receptors in nerve and immune cells of the skin, but sufficiently low so as to not result in any significant systemic exposure.