(2S,5S)-2,5-bis(propoxymethyl)pyrrolidine | 1353017-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,5S)-2,5-bis(propoxymethyl)pyrrolidine
• CAS: 1353017-23-8
• 化学式: C₁₂H₂₅NO₂
• 分子量: 215.336
• InChiKey: KJMYVEFEODHYPX-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,5S)-2,5-bis(propoxymethyl)pyrrolidine 、 碘甲烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以87%的产率得到(2S,5S)-N,N'-dimethyl-2,5-bis(propoxymethyl)pyrrolidinium iodide
  参考文献：
  名称：

  C2-Symmetric Pyrrolidine-Based Chiral Ammonium Salts as a Phase-Transfer Catalyst

  摘要：

  Chiral pyrrolidinium salts having substituents at the alpha, alpha' positions were synthesized to develop a chiral phase-transfer catalyst which have more simplified structure. The catalytic function of these synthesized catalysts was evaluated using asymmetric benzylation of N-(diphenylmethylene)glycine tert-butyl ester, and alpha,alpha'-disubstituded pyrrolidinium salts having an alkyl chain with a hydroxyl group at a chiral center were found to afford moderate enantioselectivity.

  DOI：

  10.3987/com-11-12254
• 作为产物：
  描述：

  (2S,5S)-1-<(S)-1-Phenylethyl>-2,5-bis(hydroxymethyl)pyrrolidine 在 氢气 、 palladium(II) hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 23.5h， 生成 (2S,5S)-2,5-bis(propoxymethyl)pyrrolidine
  参考文献：
  名称：

  C2-Symmetric Pyrrolidine-Based Chiral Ammonium Salts as a Phase-Transfer Catalyst

  摘要：

  Chiral pyrrolidinium salts having substituents at the alpha, alpha' positions were synthesized to develop a chiral phase-transfer catalyst which have more simplified structure. The catalytic function of these synthesized catalysts was evaluated using asymmetric benzylation of N-(diphenylmethylene)glycine tert-butyl ester, and alpha,alpha'-disubstituded pyrrolidinium salts having an alkyl chain with a hydroxyl group at a chiral center were found to afford moderate enantioselectivity.

  DOI：

  10.3987/com-11-12254

文献信息

• Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters
  作者：Minami Odagi、Kan Takayama、Makoto Sato、Masahiro Yamanaka、Kazuo Nagasawa

  DOI：10.3390/molecules200712590

  日期：——

  guanidine-bisurea bifunctional organocatalysts 5 bearing a chiral pyrrolidine moiety on guanidine were designed with the guidance of DFT calculations. The resulting organocatalysts 5 were examined for α-hydroxylation of tetralone-derived β-keto esters, and good selectivity was obtained with 5j bearing a methoxymethyl ether-containing chiral pyrrolidine moiety.

  在DFT计算的指导下，设计了在胍上带有手性吡咯烷部分的新型胍-双脲双功能有机催化剂5。检查得到的有机催化剂5的四氢萘酮衍生的β-酮酯的α-羟基化，并且用带有含甲氧基甲基醚的手性吡咯烷部分的5j获得了良好的选择性。