2-chloro-1-(3,5-dihydroxy-phenyl)-ethanone | 39878-43-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-1-(3,5-dihydroxy-phenyl)-ethanone
• 英文别名: 2-Chlor-1-(3,5-dihydroxy-phenyl)-aethanon；ω-Chlor-3,5-dihydroxyacetophenon；2-Chloro-1-(3,5-dihydroxyphenyl)ethanone
• CAS: 39878-43-8
• 化学式: C₈H₇ClO₃
• 分子量: 186.595
• InChiKey: ASZDQGFVJIMRRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-1-(3,5-dihydroxy-phenyl)-ethanone 在 盐酸 、 葡萄糖 、 水 、 四丁基碘化铵 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 aq. phosphate buffer 、 乙醚 、 乙醇 、 水 、 乙腈 为溶剂， 反应 105.0h， 生成 (R)‐5‐(2‐(tert‐butylamino)‐1‐hydroxyethyl)benzene‐1,3‐diol hydrochloride
  参考文献：
  名称：

  Chemo-enzymatic route for (R)-terbutaline hydrochloride based on microbial asymmetric reduction of a substituted α-chloroacetophenone derivative

  摘要：

  To synthesize (R)-terbutaline hydrochloride, a potent beta(2)-adrenoceptor-stimulating agent, asymmetric reduction of a substituted alpha-chloroacetophenone derivative with cultured whole-cell biocatalyst of the yeast Williopsis californica JCM 3600 was developed as the key reaction. The reduction proceeded by a si-facial attack of hydride in a highly enantioselective manner. Co-factor generation was enhanced by applying glycerol as the carbon source. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.01.020
• 作为产物：
  描述：

  3,5-二乙酰氧基苯乙酮 在 Candida antarctica lipase B 、 水 、 溴 、 溶剂黄146 、 sodium chloride 作用下， 以 aq. phosphate buffer 、 水 、 甲苯 、 乙腈 为溶剂， 反应 19.0h， 生成 2-chloro-1-(3,5-dihydroxy-phenyl)-ethanone
  参考文献：
  名称：

  Chemo-enzymatic route for (R)-terbutaline hydrochloride based on microbial asymmetric reduction of a substituted α-chloroacetophenone derivative

  摘要：

  To synthesize (R)-terbutaline hydrochloride, a potent beta(2)-adrenoceptor-stimulating agent, asymmetric reduction of a substituted alpha-chloroacetophenone derivative with cultured whole-cell biocatalyst of the yeast Williopsis californica JCM 3600 was developed as the key reaction. The reduction proceeded by a si-facial attack of hydride in a highly enantioselective manner. Co-factor generation was enhanced by applying glycerol as the carbon source. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.01.020

文献信息

• Green Synthesis of (<i>R</i>)-Terbutaline for Recyclable Catalytic Asymmetric Transfer Hydrogenation in Ionic Liquids
  作者：Hitomi Uchimoto、Miki Ikeda、Saori Tanida、Kayo Ohhashi、Yoshiko Chihara、Takashi Shigeta、Kenji Arimitsu、Masayuki Yamashita、Kiyoharu Nishide、Ikuo Kawasaki

  DOI：10.1248/cpb.c16-00949

  日期：——

  We synthesize optically active (R)-terbutaline 2, which is an anti-asthmatic drug, through recyclable catalytic asymmetric transfer hydrogenation (RCATH). Various chloroketones 4 were prepared and RCATH was performed on them. The products exhibit moderate to high enantioselectivity. In particular, the hydrogenation of acyl substituted substrates 4c yields chiral secondary alcohols 5c in good yield

  我们通过可循环的催化不对称转移氢化（RCATH）合成了光学活性（R）-特布他林2，这是一种抗哮喘药。制备了各种氯酮4并对其进行了RCATH。产物表现出中等至高的对映选择性。特别地，酰基取代的底物4c的氢化以良好的产率和对映选择性产生手性仲醇5c。此外，（R）-叔丁胺2可以在不消旋的情况下由所得仲醇5一步合成。
• DE865315
  申请人：——

  公开号：——

  公开（公告）日：——
• US4245093A
  申请人：——

  公开号：US4245093A

  公开（公告）日：1981-01-13
• Chemo-enzymatic route for (R)-terbutaline hydrochloride based on microbial asymmetric reduction of a substituted α-chloroacetophenone derivative
  作者：Shohei Taketomi、Masayoshi Asano、Toshinori Higashi、Mitsuru Shoji、Takeshi Sugai

  DOI：10.1016/j.molcatb.2012.01.020

  日期：2012.12

  To synthesize (R)-terbutaline hydrochloride, a potent beta(2)-adrenoceptor-stimulating agent, asymmetric reduction of a substituted alpha-chloroacetophenone derivative with cultured whole-cell biocatalyst of the yeast Williopsis californica JCM 3600 was developed as the key reaction. The reduction proceeded by a si-facial attack of hydride in a highly enantioselective manner. Co-factor generation was enhanced by applying glycerol as the carbon source. (C) 2012 Elsevier B.V. All rights reserved.