2-(3,5-difluorophenyl)-2-methyloxirane | 1239766-82-5

• 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: 2-(3,5-difluorophenyl)-2-methyloxirane
• CAS: 1239766-82-5
• 化学式: C₉H₈F₂O
• 分子量: 170.159
• InChiKey: LSASSXTUMQPVPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,5-difluorophenyl)-2-methyloxirane 在 sodium azide 、 palladium 10% on activated carbon 、 氢气 作用下， 以 二甲基亚砜 、 乙醇 为溶剂， 20.0 ℃ 、310.27 kPa 条件下， 以98%的产率得到(R)-1-amino-2-(3,5-difluorophenyl)propan-2-ol
  参考文献：
  名称：

  Resolution of 2,2-Disubstituted Epoxides via Biocatalytic Azidolysis

  摘要：

  A practical procedure for the enzymatic resolution of 2-alkyl-2-aryl-disubstituted epoxides using the Codex HHDH P2E2 enzyme and sodium azide is reported. This method allowed the synthesis of novel regio- and enantioselective 1-azido-2-arylpropan-2-ols in excellent yields. Furthermore, these intermediates were used for the preparation of enantiomerically enriched amino alcohols and aziridines containing a tertiary center.

  DOI：

  10.1021/ol101406k
• 作为产物：
  描述：

  三甲基碘化亚砜 、 3,5-二氟苯乙酮 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 以95%的产率得到2-(3,5-difluorophenyl)-2-methyloxirane
  参考文献：
  名称：

  Resolution of 2,2-Disubstituted Epoxides via Biocatalytic Azidolysis

  摘要：

  A practical procedure for the enzymatic resolution of 2-alkyl-2-aryl-disubstituted epoxides using the Codex HHDH P2E2 enzyme and sodium azide is reported. This method allowed the synthesis of novel regio- and enantioselective 1-azido-2-arylpropan-2-ols in excellent yields. Furthermore, these intermediates were used for the preparation of enantiomerically enriched amino alcohols and aziridines containing a tertiary center.

  DOI：

  10.1021/ol101406k

文献信息

• Recombinant Halohydrin Dehalogenase Polypeptides
  申请人：De Vries Erik

  公开号：US20100173372A1

  公开（公告）日：2010-07-08

  The present disclosure provides engineered halohydrin dehalogenase (HHDH) polypeptides having improved enzyme properties as compared to the wild-type HHDH enzyme HheC and other reference engineered HHDH polypeptides. Also provided are polynucleotides encoding the engineered HHDH enzymes, host cells capable of expressing the engineered HHDH enzymes, and methods of using the engineered HHDH enzymes to synthesize a variety of chiral compounds including chiral epoxides and chiral alcohols.
• US8187856B2
  申请人：——

  公开号：US8187856B2

  公开（公告）日：2012-05-29
• US8580555B2
  申请人：——

  公开号：US8580555B2

  公开（公告）日：2013-11-12
• [EN] RECOMBINANT HALOHYDRIN DEHALOGENASE POLYPEPTIDES<br/>[FR] POLYPEPTIDES DE HALOHYDRINE DÉSHALOGÉNASE RECOMBINANTS
  申请人：CODEXIS INC

  公开号：WO2010080635A2

  公开（公告）日：2010-07-15

  The present disclosure provides engineered halohydrin dehalogenase (HHDH) polypeptides having improved enzyme properties as compared to the wild-type HHDH enzyme HheC and other reference engineered HHDH polypeptides. Also provided are polynucleotides encoding the engineered HHDH enzymes, host cells capable of expressing the engineered HHDH enzymes, and methods of using the engineered HHDH enzymes to synthesize a variety of chiral compounds including chiral epoxides and chiral alcohols.
• Resolution of 2,2-Disubstituted Epoxides via Biocatalytic Azidolysis
  作者：Carmela Molinaro、Audrey-Anne Guilbault、Birgit Kosjek

  DOI：10.1021/ol101406k

  日期：2010.9.3

  A practical procedure for the enzymatic resolution of 2-alkyl-2-aryl-disubstituted epoxides using the Codex HHDH P2E2 enzyme and sodium azide is reported. This method allowed the synthesis of novel regio- and enantioselective 1-azido-2-arylpropan-2-ols in excellent yields. Furthermore, these intermediates were used for the preparation of enantiomerically enriched amino alcohols and aziridines containing a tertiary center.