1,1'-(hexane-1,6-diyl)bis(1H-pyrrole) | 152195-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1,1'-(hexane-1,6-diyl)bis(1H-pyrrole)
• 英文别名: 1,6-bis(1H-pyrrol-1-yl)hexane；1,1'-(Hexane-1,6-diyl)bis(1h-pyrrole)；1-(6-pyrrol-1-ylhexyl)pyrrole
• CAS: 152195-00-1
• 化学式: C₁₄H₂₀N₂
• 分子量: 216.326
• InChiKey: PWULQTVNJLVEGV-UHFFFAOYSA-N

物化性质

• 沸点：
  102-105 °C(Press: 3 Torr)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,1'-(hexane-1,6-diyl)bis(1H-pyrrole) 在 硝酸 、 乙酸酐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.58h， 生成 1,1'-(hexane-1,6-diyl)bis(N-(5-((3-(dimethylamino)propyl)carbamoyl)-1-methyl-1H-pyrrol-3-yl)-4-nitro-1H-pyrrole-2-carboxamide)
  参考文献：
  名称：

  A New DNA Minor Groove Binding Motif: Cross-Linked Lexitropsins

  摘要：

  The nitrogen atoms of central pyrrole rings on two separate tripyrrolecarboxamide strands were covalently linked through poly(methylene) chains to provide a novel class of lexitropsins potentially capable of B-DNA double-strand reading via the minor groove, CD titration experiments revealed increasingly enhanced binding of 1:1 stoichiometry to the poly(dA-dT)-poly(dA-dT) DNA from the tetrakis(methylene) linkage to the heptakis(methylene) linkage, suggesting gradually growing importance of the bidentate antiparallel side by side binding. Ethidium bromide fluorescence displacement experiments on both poly(dA-dT)-poly(dA-dT) and poly(dA)-poly(dT) DNA's supported this analysis by providing quantitative measurement of intrinsic binding constants. The heptakis(methylene) linkage offered a binding enhancement of approximately 1000 times compared with that of the monomer.

  DOI：

  10.1021/ja00095a001
• 作为产物：
  描述：

  1-(3-chloropropyl)-1H-pyrrole 在 ((R,S,R,S)-1,4,8,11-tetramethyl-1,4,8,11-tetra-azacyclotetradecane)nickel(II) perchlorate 、 四乙基碘化铵 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1,1'-(hexane-1,6-diyl)bis(1H-pyrrole)
  参考文献：
  名称：

  Radical Cycloaddition by Nickel(II) Complex-Catalyzed Electroreduction. A Method for Preparation of Pyrrolopyridine and Pyrrolopyrrole Derivatives.

  摘要：

  环烷基[α]吡咯是通过1-(2-碘乙基)吡咯与活化烯烃的还原自由基环加成反应，或通过对1-(ω-碘烷基)吡咯的环化反应而获得的，采用镍(II)络合物作为电子转移催化剂对碘化物进行电还原。

  DOI：

  10.1248/cpb.44.2020

文献信息

• Synthesis of (1H-pyrrol-2-ylsulfanyl)alkanoic acids
  作者：E. V. Rudyakova、A. N. Mirskova、G. G. Levkovskaya

  DOI：10.1134/s1070428008100205

  日期：2008.10

  (1-Benzyl-1H-pyrrol-2-ylsulfanyl)acetic acid, 2- and 3-(1-benzyl-1H-pyrrol-2-ylsulfanyl)propionic acids, 1,1'-[1,4-phenylenebis(methylene)]bis[(1H-pyrrol-2-ylsulfanyl)acetic acid], and 1,1'-(hexane-1,6-diyl)bis-[(1H-pyrrol-2-ylsulfanyl)acetic acid] were synthesized for the first time by reactions of 1-benzyl-1H-pyrrole, 1,1'-[1,4-phenylenebis(methylene)]bis(1H-pyrrole), and 1,1'-(hexane-1,6-diyl)bis(1H-pyrrole) with thiourea, iodine, and the corresponding halogen-substituted alkanoic acids. 1-(4-Nitrophenyl)-1H-pyrrole failed to react with thiourea and iodine.

  (1-苯甲基-1H-吡咯-2-基硫代)乙酸、2-和3-(1-苯甲基-1H-吡咯-2-基硫代)丙酸、1,1'-[1,4-亚苯基双(亚甲基)]双[(1H-吡咯-2-基硫代)乙酸]及1,1'-(1,6-己二基)双[(1H-吡咯-2-基硫代)乙酸]首次通过1-苯甲基-1H-吡咯、1,1'-[1,4-亚苯基双(亚甲基)]双(1H-吡咯)和1,1'-(1,6-己二基)双(1H-吡咯)与硫脲、碘及相应的卤代烷基酸反应而合成。1-(4-硝基苯基)-1H-吡咯未能与硫脲和碘反应。
• C-amidoalkylation of pyrroles with N-trifluoromethylsulfonyl and N-arylsulfonyl polychloroaldehyde imines
  作者：E. V. Kondrashov、E. V. Rudyakova、G. N. Rozentsveig、I. B. Rozentsveig、K. A. Chernyshev、L. B. Krivdin、G. G. Levkovskaya

  DOI：10.1134/s1070428009090097

  日期：2009.9

  N-(Trifluoromethylsulfonyl) and N-arylsulfonyl polychloroacetaldehyde imines reacted with pyrrole, 1-alkyl-, 1-benzyl-, and 1-(4-nitrophenyl)-substituted pyrroles, and bis-pyrroles to give the corresponding 2-[1-(sulfonylamino)polychloroethyl]-1H-pyrroles or mixtures of 2- and 3-[1-(sulfonylamino) polychloroethyl]-1H-pyrroles, depending on the nature of the Schiff base and substituent on the pyrrole nitrogen atom and reaction conditions. The first synthesis of 2,5-disubstituted NH-pyrrole by reaction of pyrrole with Schiff bases was described.
• Radical Cycloaddition by Nickel(II) Complex-Catalyzed Electroreduction. A Method for Preparation of Pyrrolopyridine and Pyrrolopyrrole Derivatives.
  作者：Shigeko OZAKI、Shizue MITOH、Hidenobu OHMORI

  DOI：10.1248/cpb.44.2020

  日期：——

  Cycloalkano[α]pyrroles were obtained by reductive radical cycloaddition of 1-(2-iodoethyl)pyrrole and activated olefins or by cyclization of 1-(ω-iodoalkyl)pyrroles, through electroreduction of the iodides using nickel(II) complex as an electron-transfer catalyst.

  环烷基[α]吡咯是通过1-(2-碘乙基)吡咯与活化烯烃的还原自由基环加成反应，或通过对1-(ω-碘烷基)吡咯的环化反应而获得的，采用镍(II)络合物作为电子转移催化剂对碘化物进行电还原。
• A New DNA Minor Groove Binding Motif: Cross-Linked Lexitropsins
  作者：Yong-Huang Chen、J. William Lown

  DOI：10.1021/ja00095a001

  日期：1994.8

  The nitrogen atoms of central pyrrole rings on two separate tripyrrolecarboxamide strands were covalently linked through poly(methylene) chains to provide a novel class of lexitropsins potentially capable of B-DNA double-strand reading via the minor groove, CD titration experiments revealed increasingly enhanced binding of 1:1 stoichiometry to the poly(dA-dT)-poly(dA-dT) DNA from the tetrakis(methylene) linkage to the heptakis(methylene) linkage, suggesting gradually growing importance of the bidentate antiparallel side by side binding. Ethidium bromide fluorescence displacement experiments on both poly(dA-dT)-poly(dA-dT) and poly(dA)-poly(dT) DNA's supported this analysis by providing quantitative measurement of intrinsic binding constants. The heptakis(methylene) linkage offered a binding enhancement of approximately 1000 times compared with that of the monomer.