2,5-diallylpyrrole | 42159-33-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,5-diallylpyrrole
• 英文别名: 2,5-diallyl-pyrrole；2,5-Diallyl-pyrrol；2,5-bis(prop-2-enyl)-1H-pyrrole
• CAS: 42159-33-1
• 化学式: C₁₀H₁₃N
• 分子量: 147.22
• InChiKey: OUCLNFUSJAVWHY-UHFFFAOYSA-N

物化性质

• 沸点：
  110-115 °C(Press: 17 Torr)
• 密度：
  0.9321 g/cm3(Temp: 24 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  2,5-diallylpyrrole 以 四氢呋喃 、 正己烷 为溶剂， 生成 8-butyl-12-azonia-8-boranuidatricyclo[6.3.1.04,12]dodeca-1(12),2-diene
  参考文献：
  名称：

  A tricyclic N-pyrrolylborane with an exceptionally stable B–N bond

  摘要：

  Hydroboration of 2,5-diallylpyrrole by using a mixture diethylborane/triethylborane (Et2BH/Et3B) leads to the first tricyclic N-pyrrolylborane 3 which possesses an exceptionally stable B-N bond. In accordance with the pronounced Lewis-acidic character of 3, it is readily converted into adducts (6) or berates (9). The crystal structure of 3 was determined by X-ray analysis (triclinic, space group , Z = 8) showing a fairly long B-N bond (mean value 144 pm), the first example of a diorgano N-pyrrolyl borane in which the pyrrole ring is not twisted against the C2BN-plane. Nuclear magnetic shielding (B-11, C-13, N-14) was calculated using the GIAO procedure, BN(pp)pi bonding is discussed on the basis of MO calculations. (C) 1998 Elsevier Science S.A.

  DOI：

  10.1016/s0022-328x(97)00587-1
• 作为产物：
  描述：

  吡咯 、 烯丙醇 在 四(三苯基膦)钯 三乙基硼 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以91%的产率得到2,5-diallylpyrrole
  参考文献：
  名称：

  Pd-catalyzed Allylic Alkylation of Pyr- roles with Allyl Alcohols Promoted by Triethylborane

  摘要：

  DOI：

  10.3987/com-05-s(t)63

文献信息

• METHODS FOR THE CONVERSION OF A SUBSTITUTED FURAN TO A SUBSTITUTED PYRROLE
  申请人：Kreischer Bruce E.

  公开号：US20120083609A1

  公开（公告）日：2012-04-05

  The present invention discloses processes for producing substituted pyrrole compounds, such as 2,5-disubstituted pyrroles. Synthetic processes which directly convert substituted furan compounds to substituted pyrrole compounds, via a reaction of the substituted furan compound with ammonia and/or an ammonium salt in the presence of a catalyst, also are described.

  本发明揭示了生产取代吡咯化合物的过程，例如2,5-二取代吡咯化合物。还描述了一种合成过程，该过程通过将取代呋喃化合物与氨和/或铵盐在催化剂存在下反应，直接转化为取代吡咯化合物。
• Preparation of an Olefin Oligomerization Catalyst
  申请人：Sydora Orson L.

  公开号：US20130150642A1

  公开（公告）日：2013-06-13

  This disclosure provides for new catalyst systems and new methods for preparing and using the catalyst systems for generating a trimerization product. In an aspect, the new catalyst systems comprise a chromium carboxylate that is prepared by anhydrous metathesis. In another aspect, the catalyst system comprise a chromium carboxylate that is prepared by anhydrous metathesis and a metal pyrrolide compound. The catalyst systems imparts improved performance and/or reduced catalyst system cost to an olefin trimerization process.

  本公开提供了新的催化剂系统和新的方法，用于制备和使用催化剂系统生成三聚物产物。在一个方面，新的催化剂系统包括通过无水交换反应制备的铬羧酸盐。在另一个方面，催化剂系统包括通过无水交换反应制备的铬羧酸盐和金属吡咯烷化合物。这些催化剂系统赋予烯烃三聚化过程改进的性能和/或降低了催化剂系统成本。
• Notizen: Synthesis of N,C,C-Trilithio-2,5-diallyl-pyrrole and its Solvent-Controlled Reactions with Electrophiles Notizen
  作者：Bernd Wrackmeyer、Iris Ordung、Bernd Schwarze

  DOI：10.1515/znb-1997-0322

  日期：1997.3.1

  2,5-Diallylpyrrole 1 reacts with an excess of ⁿBuLi in hexane/diethylether to give the N,C,Ctrilithio reagent 2. ⁷Li NMR spectra of 2 in THF/ HMPTA at low temperature indicate the presence of an ionic species. Reactions of 2 in THF with electrophiles such as H₂O, D₂O, MeI, Me₃SiCl and Me₃SnCl lead selectively to the cisisomers 3a - 6a, whereas the analogous reactions in hexane or diethylether afford mixtures containing both cis- and rram-isomers (e.g. 3b).

  2,5-二烯基吡咯1在正己烷/二乙醚中与过量的ⁿBuLi反应，生成N，C，C-三锂试剂2。⁷Li NMR谱在THF/HMPTA中表明2存在离子物种。2在THF中与电子亲和剂如H₂O、D₂O、MeI、Me₃SiCl和Me₃SnCl反应，选择性地导致顺式异构体3a-6a，而在正己烷或二乙醚中的类似反应则产生包含顺式和反式异构体（例如3b）的混合物。

• OLIGOMERIZATION CATALYST SYSTEM AND PROCESS FOR OLIGOMERIZING OLEFINS
  申请人：Sydora Orson L.

  公开号：US20100113852A1

  公开（公告）日：2010-05-06

  Among other things, this disclosure provides an olefin oligomerization system and process, the system comprising: a) a transition metal compound; b) a pyrrole compound having independently-selected C 1 to C 18 organyl groups at the 2- and 5-positions, wherein at least one of the organyl group alpha-carbon atoms attached to the 2- and 5-positions of the pyrrole compound is a secondary carbon atoms; and c) a metal alkyl. For example, the 2,5-diethylpyrrole (2,5-DEP)-based catalyst systems can afford a productivity increases over unsubstituted pyrrole catalyst systems, non-2,5-disubstituted catalyst systems, and 2,5-dimethylpyrrole (2,5-DMP) catalyst systems.

  除其他事项外，本公开提供了一种烯烃寡聚化系统和过程，该系统包括：a）过渡金属化合物；b）在2-和5-位置上具有独立选择的C1到C18有机基团的吡咯化合物，其中至少一个附加在吡咯化合物的2-和5-位置的有机基团的α-碳原子是次级碳原子；以及c）金属烷基。例如，基于2,5-二乙基吡咯（2,5-DEP）的催化剂系统可以比未取代的吡咯催化剂系统、非2,5-二取代催化剂系统和2,5-二甲基吡咯（2,5-DMP）催化剂系统提高生产力。
• Compounds useful as antiproliferative agents
  申请人：WHITBY RESEARCH, Inc.

  公开号：EP0549916A2

  公开（公告）日：1993-07-07

  Melatonin compounds are disclosed of the formula where R is hydrogen or C1 to C6 linear or branched alkylene substituted with phenyl; R1 is hydrogen, substituted benzyl, naphthylmethyl or taken together with R2 and the two carbon atoms of the five-membered hetero ring form the group where R1' is C1 to C6 linear or branched alkanoyl and R1" is hydrogen, C1 to C6 linear or branched alkyl or phenyl optionally substituted with one or more halogen, amino, nitro, hydroxy, alkyl, alkoxy or haloalkyl; R2 is hydrogen, 1-pyrrolyl, 1-pyrrolyl substituted with one or more alkyl or alkoxy, the group -(CH2)m-NHR2'1, where m is 1 to 3 and R2' is phenyl sulfonyl, the phenyl group optionally substituted with alkyl, or -C(O)-R2", where R2" is C1 to C6 linear or branched alkylene substituted with a substituent selected from the group consisting of hydrogen, phenyl, alkoxy, alkoxy substituted with phenyl, carboxylic acid or the alkyl esters thereof, carbamoyloxy alkyl, substituted carbamoyloxy alkyl and amino or 5-(2-alkanoyl) tetrazole; R3, R4, R5 and R6 are the same or different and are hydrogen, C1 to C61inear or branched alkyl, C1 to C6 linear or branched alkoxy, phenoxy or phenoxy substituted with one or more C1 to C6 linear or branched alkyl. The compounds display melatonin antagonist and are antiproliferative agents.

  褪黑素化合物的公开式为 其中 R 是氢或被苯基取代的 C1 至 C6 直链或支链亚烷基；R1 是氢、取代的苄基、萘甲基或与 R2 和五元杂环的两个碳原子一起形成基团 其中 R1'为 C1 至 C6 直链或支链烷酰基，R1 "为氢、C1 至 C6 直链或支链烷基或苯基，可选择被一个或多个卤素、氨基、硝基、羟基、烷基、烷氧基或卤代烷基取代；R2 是氢、1-吡咯基、被一个或多个烷基或烷氧基取代的 1-吡咯基、基团-(CH2)m-NHR2'1（其中 m 为 1 至 3）和 R2'是苯磺酰基（苯基可选择被烷基取代）或-C(O)-R2"、其中 R2 "是被选自氢、苯基、烷氧基、被苯基取代的烷氧基、羧酸或其烷基酯、氨基甲酰氧基烷基、取代的氨基甲酰氧基烷基和氨基或 5-（2-烷酰基）四唑的取代基取代的 C1 至 C6 直链或支链亚烷基；R3、R4、R5 和 R6 相同或不同，并且是氢、C1 至 C61 直链或支链烷基、C1 至 C6 直链或支链烷氧基、苯氧基或被一个或多个 C1 至 C6 直链或支链烷基取代的苯氧基。这些化合物具有褪黑激素拮抗作用，是抗增殖剂。