(2R,3R)-3-propyloxirane-2-carbaldehyde | 195614-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2R,3R)-3-propyloxirane-2-carbaldehyde
• CAS: 195614-97-2
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: JHKVGIOBTDDGMJ-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-propyloxirane-2-carbaldehyde 、 丁基三苯基溴化膦 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以40 mg的产率得到(2S,3R)-2-((Z)-pent-1-en-1-yl)-3-propyloxirane
  参考文献：
  名称：

  氯乙烯环氧化合物开放的立体化学研究：以环氯离子为中间体

  摘要：

  据报道，对一组开放的氯化乙烯基环氧化物进行了系统的研究，其中包括将五元和四元氯鎓离子都作为这种环氧化物开放反应中可能的中间体的实验。

  DOI：

  10.1021/acs.orglett.5b00558
• 作为产物：
  描述：

  己烯醛 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 双氧水 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 生成 (2R,3R)-3-propyloxirane-2-carbaldehyde
  参考文献：
  名称：

  Optically Active Thiophenes via an Organocatalytic One-Pot Methodology

  摘要：

  A general methodology for the synthesis of trisubstituted, optically active thiophenes by an organocatalytic one-pot reaction cascade is presented. The target products are synthesized in good yields (up to 92%) and with excellent enantioselectivities (up to 98% ee). Importantly, based on practical and easily available starting materials, the presented methodology can be conducted under mild reaction conditions. To further elucidate the generality, the synthesis of optically active thienoindoles, as well as selenophenes, is also demonstrated.

  DOI：

  10.1021/ol203237r

文献信息

• Optically Active Thiophenes via an Organocatalytic One-Pot Methodology
  作者：Lars Krogager Ransborg、Łukasz Albrecht、Christian F. Weise、Jesper R. Bak、Karl Anker Jørgensen

  DOI：10.1021/ol203237r

  日期：2012.2.3

  A general methodology for the synthesis of trisubstituted, optically active thiophenes by an organocatalytic one-pot reaction cascade is presented. The target products are synthesized in good yields (up to 92%) and with excellent enantioselectivities (up to 98% ee). Importantly, based on practical and easily available starting materials, the presented methodology can be conducted under mild reaction conditions. To further elucidate the generality, the synthesis of optically active thienoindoles, as well as selenophenes, is also demonstrated.
• Stereochemical Studies of the Opening of Chloro Vinyl Epoxides: Cyclic Chloronium Ions as Intermediates
  作者：Andrej Shemet、David Sarlah、Erick M. Carreira

  DOI：10.1021/acs.orglett.5b00558

  日期：2015.4.17

  A systematic study of the opening of a collection of chlorinated vinyl epoxides is reported, which includes experiments that implicate both five- and four-membered chloronium ions as plausible intermediates in this type of epoxide opening reaction.

  据报道，对一组开放的氯化乙烯基环氧化物进行了系统的研究，其中包括将五元和四元氯鎓离子都作为这种环氧化物开放反应中可能的中间体的实验。