3-hexyl-oxirane-2-carbaldehyde | 908008-80-0

• 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: 3-hexyl-oxirane-2-carbaldehyde
• 英文别名: 3-Hexyloxirane-2-carbaldehyde；3-hexyloxirane-2-carbaldehyde
• CAS: 908008-80-0
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: CXWONQXFWHZHPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  3-hexyl-oxirane-2-carbaldehyde 、 氘代甲醇 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 18.25h， 生成 trideuteromethyl (R)-3-hydroxynonanoate
  参考文献：
  名称：

  Organocatalytic Preparation of Simple β-Hydroxy and β-Amino Esters: Low Catalyst Loadings and Gram-Scale Synthesis

  摘要：

  A combined amino- and N-heterocyclic carbene (NHC)-catalyzed one-pot reaction sequence for the synthesis of simple enantioenriched beta-hydroxy and beta-amino esters using commercially available catalysts at low catalyst loadings has been developed. The desired products were obtained in high yield and excellent enantiopurity. The generation of quaternary stereocenters and application in gram-scale synthesis were also realized, with no requirements of inert or anhydrous reaction conditions, thus making this transformation a highly practical protocol.

  DOI：

  10.1021/ol102164y
• 作为产物：
  描述：

  反式-2-壬烯醛 生成 3-hexyl-oxirane-2-carbaldehyde
  参考文献：
  名称：

  烯类化合物环氧化的不对称抗衡离子导向催化。

  摘要：

  DOI：

  10.1002/anie.200704185

文献信息

• Asymmetric Epoxidation of α,β-Unsaturated Aldehydes in Aqueous Media Catalyzed by Resin-Supported Peptide- Containing Unnatural Amino Acids
  作者：Kengo Akagawa、Kazuaki Kudo

  DOI：10.1002/adsc.201000805

  日期：2011.4.18

  The enantio‐ and diastereoselective epoxidation of α,β‐unsaturated aldehydes in aqueous media was realized using a resin‐supported peptide catalyst. Introducing the hydrophobic and bulky unnatural amino acid 3‐(1‐pyrenyl)alanine into the peptide sequence was effective for enhancing the reaction rate and enantioselectivity.

  使用树脂负载的肽催化剂可实现水性介质中α，β-不饱和醛的对映体和非对映体选择性环氧化。在肽序列中引入疏水和庞大的非天然氨基酸3-（1-吡啶基）丙氨酸可有效提高反应速度和对映选择性。
• Asymmetric Counteranion-Directed Catalysis for the Epoxidation of Enals
  作者：Xingwang Wang、Benjamin List

  DOI：10.1002/anie.200704185

  日期：2008.1.25
• Organocatalytic Preparation of Simple β-Hydroxy and β-Amino Esters: Low Catalyst Loadings and Gram-Scale Synthesis
  作者：Hao Jiang、Björn Gschwend、Łukasz Albrecht、Karl Anker Jørgensen

  DOI：10.1021/ol102164y

  日期：2010.11.5

  A combined amino- and N-heterocyclic carbene (NHC)-catalyzed one-pot reaction sequence for the synthesis of simple enantioenriched beta-hydroxy and beta-amino esters using commercially available catalysts at low catalyst loadings has been developed. The desired products were obtained in high yield and excellent enantiopurity. The generation of quaternary stereocenters and application in gram-scale synthesis were also realized, with no requirements of inert or anhydrous reaction conditions, thus making this transformation a highly practical protocol.