(R)-(-)-2-(3,4-dimethoxybenzyl)oxirane | 165821-74-9

• 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)-(-)-2-(3,4-dimethoxybenzyl)oxirane
• 英文别名: (2R)-2-[(3,4-dimethoxyphenyl)methyl]oxirane
• CAS: 165821-74-9
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: IDIQAXMVNSQLSC-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-(3,4-dimethoxybenzyl)oxirane 在 硼烷 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 (R)-2-(3,4-二甲氧基苄基)-吡咯烷
  参考文献：
  名称：

  Enantioselective Synthesis of 2-Substituted Pyrrolidines from 4-Hydroxynitriles. Application to the Synthesis of the Dopamine Agonist rs-59022

  摘要：

  Two novel routes to optically active 4-hydroxynitriles and the subsequent cyclization to 2-substituted pyrrolidines are described. The methodology is applied to the synthesis of the key intermediate used in the synthesis of the dopamine agonist RS-59022. Unusual selectivity in the CBS reduction of 4-oxonitriles is explained through structural and mechanistic analysis.

  DOI：

  10.1080/00397919508012679
• 作为产物：
  描述：

  4-溴黎芦醚 在 正丁基锂 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.17h， 生成 (R)-(-)-2-(3,4-dimethoxybenzyl)oxirane
  参考文献：
  名称：

  Enantioselective Synthesis of 2-Substituted Pyrrolidines from 4-Hydroxynitriles. Application to the Synthesis of the Dopamine Agonist rs-59022

  摘要：

  Two novel routes to optically active 4-hydroxynitriles and the subsequent cyclization to 2-substituted pyrrolidines are described. The methodology is applied to the synthesis of the key intermediate used in the synthesis of the dopamine agonist RS-59022. Unusual selectivity in the CBS reduction of 4-oxonitriles is explained through structural and mechanistic analysis.

  DOI：

  10.1080/00397919508012679

文献信息

• Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation
  作者：Muriel Amatore、Teresa D. Beeson、Sean P. Brown、David W. C. MacMillan

  DOI：10.1002/anie.200901855

  日期：2009.6.29

  Time for SOme MOre: For the first time SOMO (singly occupied molecular orbital) activation has been exploited to allow a new approach to the α‐chlorination of aldehydes. This transformation can be readily implemented as part of a linchpin catalysis approach to the enantioselective production of terminal epoxides.

  SOme MOre 时间：首次利用 SOMO（单占据分子轨道）激活来实现醛的 α-氯化的新方法。这种转化可以很容易地作为对映选择性生产末端环氧化物的关键催化方法的一部分来实现。
• Asymmetric Epoxidation of Terminal Alkenes with Hydrogen Peroxide Catalyzed by Pentafluorophenyl Pt^II Complexes
  作者：Marco Colladon、Alessandro Scarso、Paolo Sgarbossa、Rino A. Michelin、Giorgio Strukul

  DOI：10.1021/ja0647607

  日期：2006.11.1

  Easily accessible chiral PtII complexes 1 allow highly enantioselective and completely regioselective asymmetric epoxidation of terminal alkenes with hydrogen peroxide

  容易获得的手性 PtII 复合物 1 允许末端烯烃与过氧化氢的高度对映选择性和完全区域选择性不对称环氧化
• Towards a Greener Epoxidation Method: Use of Water-Surfactant Media and Catalyst Recycling in the Platinum-Catalyzed Asymmetric Epoxidation of Terminal Alkenes with Hydrogen Peroxide
  作者：Marco Colladon、Alessandro Scarso、Giorgio Strukul

  DOI：10.1002/adsc.200600518

  日期：2007.4.2

  Remarkable improvements in enantioselectivity as well as recycle were observed in the catalytic asymmetric epoxidation of terminal alkenes with a chiral, electron-poor platinum(II) catalyst with hydrogen peroxide as terminal oxidant in water-surfactant media.

  在水表面活性剂介质中，用过氧化氢作为末端氧化剂的手性，电子贫化的铂（II）催化剂，末端烯烃的催化不对称环氧化反应中，对映选择性和循环性都有显着改善。
• Enantioselective Synthesis of 2-Substituted Pyrrolidines from 4-Hydroxynitriles. Application to the Synthesis of the Dopamine Agonist rs-59022
  作者：Owen W. Gooding、Rekha P. Bansal

  DOI：10.1080/00397919508012679

  日期：1995.4

  Two novel routes to optically active 4-hydroxynitriles and the subsequent cyclization to 2-substituted pyrrolidines are described. The methodology is applied to the synthesis of the key intermediate used in the synthesis of the dopamine agonist RS-59022. Unusual selectivity in the CBS reduction of 4-oxonitriles is explained through structural and mechanistic analysis.