2-(2,6-Diisopropylphenylaminomethylene) indole | 1448614-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(2,6-Diisopropylphenylaminomethylene) indole
• 英文别名: N-[2,6-di(propan-2-yl)phenyl]-1-(1H-indol-2-yl)methanimine
• CAS: 1448614-80-9
• 化学式: C₂₁H₂₄N₂
• 分子量: 304.435
• InChiKey: YDCNRLFQKNMRCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2,6-Diisopropylphenylaminomethylene) indole 在 正丁基锂 、 三氯硅烷 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 12.5h， 以75%的产率得到
  参考文献：
  名称：

  Hydrosilylation in imino-substituded N- or C-monoanionic ligands

  摘要：

  The reaction of HSiCl3 with 24[N-(2,6-diisopropylphenyl)iminomethyl]indolyl lithium (DipplMlndLi) provided disubstituted (DippAMInd)(DipplMlnd)SiCl (2), where one imino moiety of DipplMlnd ligand was reduced to amino group by Si-H fragment. In contract the reaction of HSiCl3 with 2-[N-(2,6-diisopropylphenyl)iminomethyl]phenyl lithium (DippIMPhLi) provided stable CH=N -> Si coordinated silane (DippIMPh)SiHCl2 (3). Heating of the toluene solution of 3 provided the hydrosilylated compound (DippAMPh)SiCl2 (4). It has been demonstrated that the rate of CH=N imino group reduction strongly depends on type of the anionic ligand. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2016.07.042
• 作为产物：
  描述：

  1H-吲哚-2-甲醛 、 2,6-二异丙基苯胺 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 生成 2-(2,6-Diisopropylphenylaminomethylene) indole
  参考文献：
  名称：

  芳环稠合亚氨基吡咯基配体的硼配合物：合成，结构和发光性能†

  摘要：

  2-甲酰基吲哚（1）或2-甲酰基菲[ 9,10 - c ]吡咯（2）与各种芳族胺的缩合反应得到相应的苯基或菲环稠合的单-/双-亚氨基吡咯配体前体3-8。 ，以适当的摩尔比与BPh 3反应，生成新的单硼和双硼螯合物Ph 2 B [NC 8 H 5 C（H）N -2,6-Ar]（Ar = 2,6-iPr 2 C 6 H 3 9 ; C 6 H 5 10），Ph 2 B [（NC 8 H5 C（H）N） 2 -1,4-C 6 H 4 ] BPh 2 11，Ph 2 B（NC 16 H 9 C（H） N -Ar）（Ar = 2,6-iPr 2 C 6 H 3 12； C 6 H 5 13）和Ph 2 B [（NC 16 H 9 C（H）N） 2 -1,4-C 6 H 4 ] BPh 2 14。硼配合物12-14含有与吡咯基C3–C4键融合的菲片段的溶液在溶液中具有很高的荧光性，量子效率分别为37％

  DOI：

  10.1039/c6dt02771g

文献信息

• Synthesis, Structure, and Reactivity of Lanthanide Complexes Incorporating Indolyl Ligands in Novel Hapticities
  作者：Zhijun Feng、Xiancui Zhu、Shaoyin Wang、Shaowu Wang、Shuangliu Zhou、Yun Wei、Guangchao Zhang、Baojia Deng、Xiaolong Mu

  DOI：10.1021/ic401515q

  日期：2013.8.19

  in the novel μ-η6:η1:η1 hapticities with the reduction of europium(III) to europium(II) and the oxidation of amino to imino group. Reaction of 2-(2,6-diisopropylphenylaminomethylene)indole 2-(2,6-i-Pr2C6H3NHCH2)C8H5NH (1) with ytterbium(III) amide [(Me3Si)2N]3YbIII(μ-Cl)Li(THF)3 produced the only deprotonated ytterbium(III) complex formulated as [2-(2,6-i-Pr2C6H3NCH2)C8H5N]Yb[N(SiMe3)2](THF)2 (3), having

  描述了2-（2，6-二异丙基苯基氨基亚甲基）吲哚配体（1）与euro和酰胺的相互作用的化学反应。2-（2,6-二异丙基苯基氨基亚甲基）吲哚2-（2,6- i- Pr 2 C 6 H 3 NHCH 2）C 8 H 5 NH（1）与euro酰胺[（Me 3 Si）2 N]的反应3铕III（μ-Cl）的锂（THF）3，得到的新的铕（II）配合物配制为[μ-η 6：η 1：η 1 -2-（2,6-我-Pr 2Ç 6 ħ 3 N = CH）C 8 H ^ 5 N]铕[2-（2,6-我-Pr 2 ç 6 ħ 3 N = CH）C 8 H ^ 5 N]} 2（2），具有桥接吲哚基配体的新型μ-η 6：η 1：η 1个hapticities与（III）的还原铕的铕（II）和氨基至亚氨基的氧化。2-（2,6-二异丙基苯基氨基亚甲基）吲哚2-（2,6- i -Pr 2 C 6 H 3 NHCH 2）C 8 H的反应5
• Synthesis and Reactivity of Rare-Earth-Metal Monoalkyl Complexes Supported by Bidentate Indolyl Ligands and Their High Performance in Isoprene 1,4-cis Polymerization
  作者：Guangchao Zhang、Shaowu Wang、Shuangliu Zhou、Yun Wei、Liping Guo、Xiancui Zhu、Lijun Zhang、Xiaoxia Gu、Xiaolong Mu

  DOI：10.1021/acs.organomet.5b00467

  日期：2015.9.14

  A series of novel rare-earth-metal monoalkyl complexes incorporating partially rotation restricted [N,1\1]-bidentate indolyl ligands were synthesized and characterized, and their reactivities and catalytic activities were investigated. Treatment of [RE-(CH2SiMe3)(3)(thf)(2)] with 1 equiv of 2-[(N-2,6-diisopropylphenyl)-iminomethyl)]indole (2-(2,6-(Pr2C6H3N)-Pr-i=CH)C8H5NH) in toluene at room temperature afforded the rare-earth-metal monoalkyl complexes [eta(1):eta(1)-2-(2,6-(Pr2C6H3N)-Pr-i=CH)Ind](2)RE(CH2SiMe3)(thf) (Ind = indolyl; RE = Yb (1), Er (2), Y (3), Dy (4), Gd (5)) and the samarium complex [eta(1):eta(1)-2-(2,6-(Pr2C6H3N)-Pr-i=CH)Ind](3)Sm (6) via alkane elimination in good yields. Treatment of complex 2 or 3 with 1 equiv of PhSiH3 in toluene at 80 degrees C for 12 h afforded the dinuclear complexes [mu-eta(6):eta(1):eta(I)-2-(2,6-(Pr2C6H3NCH2)-Pr-i)Ind]RE[2-(2,6-(Pr2C6H3N)-Pr-i=CH)Ind]}(2) (Ind = indolyl, RE = Er (7), Y (8)) in good isolated yields. Treatment of complex 2 or 3 with 1 equiv of amidine (2,6-(Pr2C6H3)-Pr-i)N=CHNH(2,6-(Pr2C6H3)-Pr-i) in toluene produced the corresponding complexes [eta(1):eta(1)-2-(2,6-(Pr2C6H3N)-Pr-i=CH)C8H5M2RE[(2,6-(Pr2C6H3)-Pr-i)N=CHN(2,6-(Pr2C6H3)-Pr-i)] (RE = Er (9), Y (10)) possessing the amidinate ligand [(2,6-iPr(2)C(6)H(3)N)(2)CH](-). The molecular structures of all complexes were determined by X-ray crystallography. The monoalkyl complexes 1-5 were tested as isoprene polymerization initiators. Among the complexes investigated, the optimum combination 5/Al'Bu-3/[Ph3C][B(C6F5)(4)] displayed a high catalytic activity in isoprene polymerization, producing polymers with an extremely high 1,4-cis selectivity (up to 99%), a high number-average molecular weight (M-n = 7.2 x 10(5)), and a narrow molecular weight distribution (PDI = 1.34) at an isoprene to initiator molar ratio of 6000:1.