3-undecyl-1H-pyrrole | 106369-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-undecyl-1H-pyrrole
• CAS: 106369-37-3
• 化学式: C₁₅H₂₇N
• 分子量: 221.386
• InChiKey: IYRUORCSLPYFCP-UHFFFAOYSA-N

物化性质

• 沸点：
  326.4±11.0 °C(Predicted)
• 密度：
  0.888±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  4-甲氧基-2,2'-联吡咯-5-甲醛 、 3-undecyl-1H-pyrrole 在 PigC from Pseudomonas putida pig-r2 ΔpigD strain 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 C₂₅H₃₅N₃O
  参考文献：
  名称：

  New Prodigiosin Derivatives Obtained by Mutasynthesis in Pseudomonas putida

  摘要：

  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.

  DOI：

  10.1021/acssynbio.7b00099
• 作为产物：
  描述：

  1-(甲苯-4-磺酰基)-3-十一烷基-1H-吡咯 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3-undecyl-1H-pyrrole
  参考文献：
  名称：

  通过使用 N-(对甲苯磺酰基甲基)-对甲苯磺酰胺作为甲胺的等价物进行新的有效氨基甲基化。吡咯化合物的方便制备

  摘要：

  容易获得的 N-(对甲苯磺酰基甲基)-对甲苯磺酰胺用碱处理以生成 N-亚甲基-对甲苯磺酰胺，其与多种亲核试剂反应以良好的产率形成相应的 N-甲苯磺酰基-氨基甲基化化合物。此外，由此获得的N-甲苯磺酰基-氨基甲基化缩醛在酸催化剂的帮助下以优异的产率转化为相应的N-甲苯磺酰基吡咯。

  DOI：

  10.1246/cl.1986.1033

文献信息

• KINOSHITA HIDEKI; INOMATA KATSUHIKO; HAYASHI MASATOSHI; KONDOH TAKESHI; K+, CHEM. LETT.,(1986) N 6, 1033-1036
  作者：KINOSHITA HIDEKI、 INOMATA KATSUHIKO、 HAYASHI MASATOSHI、 KONDOH TAKESHI、 K+

  DOI：——

  日期：——
• 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.
• A NEW AND EFFECTIVE AMINOMETHYLATION BY THE USE OF<i>N</i>-(<i>p</i>-TOLUENESULFONYLMETHYL)-<i>p</i>-TOLUENESULFONAMIDE AS AN EQUIVALENT OF METHANIMINE. A CONVENIENT PREPARATION OF PYRROLE COMPOUNDS
  作者：Hideki Kinoshita、Katsuhiko Inomata、Masatoshi Hayashi、Takeshi Kondoh、Hiroshi Kotake

  DOI：10.1246/cl.1986.1033

  日期：1986.6.5

  N-(p-toluenesulfonylmethyl)-p-toluenesulfonamide was treated with base to generate N-methylene-p-toluenesulfonamide which reacted with a variety of nucleophiles forming the corresponding N-tosyl-aminomethylated compounds in good yields. Furthermore, the N-tosyl-aminomethylated acetals thus obtained were converted into the corresponding N-tosylpyrroles with the aid of acid catalyst in excellent yields.

  容易获得的 N-(对甲苯磺酰基甲基)-对甲苯磺酰胺用碱处理以生成 N-亚甲基-对甲苯磺酰胺，其与多种亲核试剂反应以良好的产率形成相应的 N-甲苯磺酰基-氨基甲基化化合物。此外，由此获得的N-甲苯磺酰基-氨基甲基化缩醛在酸催化剂的帮助下以优异的产率转化为相应的N-甲苯磺酰基吡咯。