2-pyrrol-1-yl-propionaldehyde | 52687-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-pyrrol-1-yl-propionaldehyde
• 英文别名: 2-Pyrrol-1-ylpropanal
• CAS: 52687-80-6
• 化学式: C₇H₉NO
• 分子量: 123.155
• InChiKey: PLVVVRGZOHMSNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-pyrrol-1-yl-propionaldehyde 、 phenylmagnesium bromide 以94%的产率得到
  参考文献：
  名称：

  KASHIMA, CHOJI;MARUYAMA, TATSUYA;FUJIOKA, YOKO;HARADA, KAZUO, J. CHEM. SOC. PERKIN TRANS. PT. 1,(1989) N, C. 1041-1046

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(pyrrol-1-yl)propanal 以 四氢呋喃 为溶剂， 反应 15.0h， 以40%的产率得到2-pyrrol-1-yl-propionaldehyde
  参考文献：
  名称：

  Kashima, Choji; Maruyama, Tatsuya; Fujioka, Yoko, Journal of the Chemical Society. Perkin transactions I, 1989, p. 1041 - 1046

  摘要：

  DOI：

文献信息

• High α-regioselectivity in the rhodium-catalyzed hydroformylation of vinylpyrroles
  作者：Roberta Settambolo、Aldo Caiazzo、Raffaello Lazzaroni

  DOI：10.1016/0022-328x(95)05978-x

  日期：1996.1

  The Rh4(CO)12-catalyzed hydroformylation at low temperature (40°C) of the 1-, 2- and 3-vinylpyrrole gives the corresponding branched aldehydes 2-(1-pyrrolyl)propanal, 2-(2-pyrollyl)propanal and 2-(3-pyrrolyl)propanal with high α-regioselectivity.

  1-，2-和3-乙烯基吡咯在低温（40°C）下经Rh 4（CO）12催化的加氢甲酰化反应生成相应的支链醛2-（1-吡咯基）丙醛，2-（2-吡咯基） α-区域选择性高的丙醛和2-（3-吡咯基）丙醛。
• Evolution of a Synthetic Strategy for Complex Polypyrrole Alkaloids: Total Syntheses of Curvulamine and Curindolizine
  作者：Jun Xuan、Karl T. Haelsig、Michael Sheremet、Paulo A. Machicao、Thomas J. Maimone

  DOI：10.1021/jacs.0c13465

  日期：2021.2.24

  evolution of a synthetic program aimed at accessing the flagship metabolites curvulamine and curindolizine which are presumably a dimer and trimer of a C10N biosynthetic building block, respectively. Starting with curvulamine, we detail several strategies to merge two simple, bioinspired fragments, which while ultimately unsuccessful, led us toward a pyrroloazepinone building block-based strategy and an improved

  最近从Curvularia sp.中分离出结构上前所未有的含有多个富电子吡咯单元的抗菌生物碱。和Bipolaris maydis真菌。本文记录了旨在获取旗舰代谢物 curvulamine 和 curindolizine 的合成程序的演变，这些代谢物可能是 C 10的二聚体和三聚体N 生物合成构件，分别。从 curvulamine 开始，我们详细介绍了几种策略来合并两个简单的、受生物启发的片段，虽然最终没有成功，但我们转向了基于 pyrroloazepinone 构建单元的策略和改进的这种 10π-芳族杂环的合成。然后设计了一个两步成环工艺以锻造保守的四环双吡咯结构并推进到各种后期中间体；然而，不幸的是，脱羧失败阻碍了curvulamine的全合成。通过定制我们的环化前体，最终通过使用氰醇亲核试剂实现了 10 步全合成曲维胺的成功。然后尝试实现curvulamine与额外的C 10的仿生耦合
• Influence of the reaction temperature on the regioselectivity in the rhodium-catalyzed hydroformylation of vinylpyrroles
  作者：Aldo Caiazzo、Roberta Settambolo、Gloria Uccello-Barretta、Raffaello Lazzaroni

  DOI：10.1016/s0022-328x(97)00479-8

  日期：1997.12

  The influence of the temperature on the regioselectivity in the hydroformylation of the vinylpyrrole isomers and of the corresponding N-tosylated substrates has been investigated in the range 20-100 degrees C, in the presence of Rh-4(CO)(12). Ar all the temperatures the branched aldehyde was prevailing with respect to the linear isomer for all the substrates (I cu-regioselectivity). With increasing temperature, an increase of the linear aldehyde was observed to a different extent in dependence on the substrate nature. H-2 NMR investigation of the crude reaction mixture recovered from deuterioformylation of 3-vinylpyrrole at partial substrate conversion points out that the observed depression of the alpha-regioselectivity with increasing temperature must be connected to a beta-hydride elimination process occurring for the branched alkyl-rhodium intermediates but not for the linear ones. (C) 1997 Elsevier Science S.A.