2-methyl-3-(2-propenyl)pyrrole | 85121-14-8

• 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-methyl-3-(2-propenyl)pyrrole
• 英文别名: 3-allyl-2-methyl-1H-pyrrole；2-methyl-3-prop-2-enyl-1H-pyrrole
• CAS: 85121-14-8
• 化学式: C₈H₁₁N
• mdl: MFCD02823684
• 分子量: 121.182
• InChiKey: YEQDFKRDEGABJS-UHFFFAOYSA-N

物化性质

• 沸点：
  90 °C(Press: 8 Torr)
• 密度：
  0.8956 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(2-propenyl)pyrrole 在 氢氧化钾 、 二甲基亚砜 作用下， 反应 1.5h， 生成 (Z)-3-methyl-3-(1-propenyl)pyrrole 、 (E)-3-methyl-3-(1-propenyl)pyrrole
  参考文献：
  名称：

  5-己烯-2-酮肟的烯基化：Trofimov反应条件下的质子异构化

  摘要：

  DOI：

  10.1007/bf00766996
• 作为产物：
  描述：

  hex-5-en-2-one oxime 、 乙炔 在 氢氧化钾 作用下， 以 水 、 二甲基亚砜 为溶剂， 100.0 ℃ 、344.73 kPa 条件下， 反应 1.0h， 以30%的产率得到2-methyl-3-(2-propenyl)pyrrole
  参考文献：
  名称：

  An example of a novel synthetic approach to alkenylpyrroles

  摘要：

  DOI：

  10.1016/s0040-4039(00)85573-2

文献信息

• New Prodigiosin Derivatives Obtained by Mutasynthesis in <i>Pseudomonas putida</i>
  作者：Andreas S. Klein、Andreas Domröse、Patrick Bongen、Hannah U. C. Brass、Thomas Classen、Anita Loeschcke、Thomas Drepper、Luca Laraia、Sonja Sievers、Karl-Erich Jaeger、Jörg Pietruszka

  DOI：10.1021/acssynbio.7b00099

  日期：2017.9.15

  The deeply red-colored natural compound prodigiosin is a representative of the prodiginine alkaloid family, which possesses bioactivities as antimicrobial, antitumor, and antimalarial agents. Various bacteria including the opportunistic human pathogen Serratia marcescens and different members of the Streptomycetaceae and Pseudoalteromonadaceae produce prodiginines. In addition, these microbes generally accumulate many structurally related alkaloids making efficient prodiginine synthesis and purification difficult and expensive. Furthermore, it is known that structurally different natural prodiginine variants display differential bioactivities. In the herein described mutasynthesis approach, 13 different derivatives of prodigiosin were obtained utilizing the GRAS (generally recognized as safe) classified strain Pseudomonas putida KT2440. Genetic engineering of the prodigiosin pathway together with incorporation of synthetic intermediates thus resulted in the formation of a so far unprecedented structural diversity of new prodiginine derivatives in P. putida. Furthermore, the formed products allow reliable conclusions regarding the substrate specificity of PigC, the final condensing enzyme in the prodigiosin biosynthesis pathway of S. marcescens. The biological activity of prodigiosin toward modulation of autophagy was preserved in prodiginine derivatives. One prodiginine derivative displayed more potent autophagy inhibitory activity than the parent compound or the synthetic clinical candidate obatoclax.
• MIKHALEVA, A. I.;SIGALOV, M. V.;KALABIN, G. A., TETRAHEDRON LETT., 1982, 23, N 48, 5063-5066
  作者：MIKHALEVA, A. I.、SIGALOV, M. V.、KALABIN, G. A.

  DOI：——

  日期：——
• An example of a novel synthetic approach to alkenylpyrroles
  作者：A.I. Mikhaleva、M.V. Sigalov、G.A. Kalabin

  DOI：10.1016/s0040-4039(00)85573-2

  日期：1982.1
• Alkenylation by 5-hexen-2-one oxime: Prototropic isomerization under trofimov reaction conditions
  作者：A. M. Vasil'tsov、A. I. Mikhaleva、R. N. Nesterenko、M. V. Sigalov

  DOI：10.1007/bf00766996

  日期：1992.4