(S)-3-(4-chlorophenyl)-3-(1-methyl-1H-pyrrol-2-yl)propanal | 1384272-09-6

• 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: (S)-3-(4-chlorophenyl)-3-(1-methyl-1H-pyrrol-2-yl)propanal
• 英文别名: (3S)-3-(4-chlorophenyl)-3-(1-methylpyrrol-2-yl)propanal
• CAS: 1384272-09-6
• 化学式: C₁₄H₁₄ClNO
• 分子量: 247.724
• InChiKey: CPWPIFQRMAHWMT-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-甲基吡咯 、 4-氯肉桂醛 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以71%的产率得到(S)-3-(4-chlorophenyl)-3-(1-methyl-1H-pyrrol-2-yl)propanal
  参考文献：
  名称：

  A Click Strategy for the Immobilization of MacMillan Organocatalysts onto Polymers and Magnetic Nanoparticles

  摘要：

  A chemically modified, first generation MacMillan imidazolidin-4-one has been anchored onto 1% DVB Merrifield resin and Fe3O4 (5.3 +/- 1.4 nm) magnetic nanoparticles through copper-catalyzed alkyne azide cycloaddition (CuAAC) reactions. The resulting immobilized catalysts have been successfully used in the asymmetric Friedel-Crafts alkylation of N-substituted pyrroles with alpha,beta-unsaturated aldehydes. The PS-supported catalyst (B) showed higher catalytic activity and enantioselectivity, while the MNP-supported one (A) showed higher recyclability and could be used in a sequential process with intermediate magnetic decantation.

  DOI：

  10.1021/ol301515d

文献信息

• Multivalent polyglycerol supported imidazolidin-4-one organocatalysts for enantioselective Friedel–Crafts alkylations
  作者：Tommaso Pecchioli、Manoj Kumar Muthyala、Rainer Haag、Mathias Christmann

  DOI：10.3762/bjoc.11.83

  日期：——

  The first immobilization of a MacMillan’s first generation organocatalyst onto dendritic support is described. A modified tyrosine-based imidazolidin-4-one was grafted to a soluble high-loading hyperbranched polyglycerol via a copper-catalyzed alkyne–azide cycloaddition (CuAAC) reaction and readily purified by dialysis. The efficiency of differently functionalized multivalent organocatalysts 4a–c was tested in the asymmetric Friedel–Crafts alkylation of N-methylpyrrole with α,β-unsaturated aldehydes. A variety of substituted enals was investigated to explore the activity of the catalytic system which was also compared with monovalent analogues. The catalyst 4b showed excellent turnover rates and no loss of activity due to immobilization, albeit moderate enantioselectivities were observed. Moreover, easy recovery by selective precipitation allowed the reuse of the catalyst for three cycles.

  首次将MacMillan的第一代有机催化剂固定在树枝状载体上。一种改性的基于酪氨酸的咪唑啉-4-酮通过铜催化的炔烃-叠氮化物环加成反应（CuAAC）被嫁接到可溶的高负载超支化聚甘油上，并通过透析轻松纯化。测试了不同功能化的多价有机催化剂4a-c在N-甲基吡咯与α,β-不饱和醛的不对称Friedel–Crafts烷基化反应中的效率。研究了多种取代的烯醛，以探索催化系统的活性，并将其与单价类似物进行了比较。催化剂4b显示出优秀的转化率，并且由于固定化而未损失活性，尽管观察到适中的对映选择性。此外，通过选择性沉淀的简易回收使得催化剂可以循环使用三次。