N,N,N',N'-tetraisopropylethylenediamine | 104017-39-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N,N',N'-tetraisopropylethylenediamine
• 英文别名: N,N,N',N'-Tetraisopropyl-ethylenediamine；N,N,N',N'-tetra(propan-2-yl)ethane-1,2-diamine
• CAS: 104017-39-2
• 化学式: C₁₄H₃₂N₂
• 分子量: 228.421
• InChiKey: MUESDKXVLSXRPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  四次甲氨基乙硼烷 、 N,N,N',N'-tetraisopropylethylenediamine 生成
  参考文献：
  名称：

  895.四烷基二甲基氨基二硼与脂肪族二胺的氨基转移

  摘要：

  DOI：

  10.1039/jr9620004648
• 作为产物：
  描述：

  N,N,N',N'-tetraisopropyloxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以5.92 g的产率得到N,N,N',N'-tetraisopropylethylenediamine
  参考文献：
  名称：

  N- Boc吡咯烷的两配体催化不对称去质子化：探测化学计量配体的作用†

  摘要：

  为了确定N- Boc吡咯烷的二配体催化不对称去质子化中的化学计量配体要求，已经评估了24个不同的配体；通过在0.3当量的（-）-天冬氨酸和1.3当量的环己二胺衍生的配体存在下使用s -BuLi获得最高的对映选择性（90:10 er）。

  DOI：

  10.1021/jo8010655
• 作为试剂：
  描述：

  一氧化碳 、 2-allyl-phenylamine 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 N,N,N',N'-tetraisopropylethylenediamine 、 氢气 作用下， 以 四氢呋喃 为溶剂， 100.0 ℃ 、4.83 MPa 条件下， 反应 24.0h， 以31%的产率得到3-甲基-1,2,3,4-四氢喹啉
  参考文献：
  名称：

  Ionic diamine rhodium complex catalyzed hydroaminomethylation of 2-allylanilines

  摘要：

  Ionic diamine rhodium complexes catalyze the hydroaminomethylation of 2-allylanilines. The reaction involves initial hydroformylation followed by reductive amination, which provides direct access to 1,2,3,4-tetrahydroquinolines and 2,3,4,5-1H-1-benzazepines. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.048

文献信息

• Charge-Transfer Complex Promoted Regiospecific C−N Bond Cleavage of Vicinal Tertiary Diamines
  作者：Ying Fu、Qin-Shan Xu、Chun-Zhao Shi、Zhengyin Du、Caiqin Xiao

  DOI：10.1002/adsc.201800591

  日期：2018.9.17

  A catalyst‐free, charge‐transfer complex promoted coupling of sulfonyl chlorides with vicinal tertiary diamines to generate sulfonamides is presented. Mechanistic studies showed that these reactions are proceeded via charge transfer of vicinal tertiary diamines to sulfonyl chlorides, forming the unstable sulfonyl quaternary ammonium like complexes which induced the regiospecific intramolecular C−N

  提出了一种无催化剂，电荷转移的复合物，可促进磺酰氯与邻位叔二胺的偶联，从而生成磺酰胺。机理研究表明，这些反应是通过将邻位叔二胺电荷转移至磺酰氯而进行的，形成了不稳定的磺酰基季铵盐状复合物，从而诱导了邻位叔二胺的区域特异性分子内C-N键裂解。
• A Highly Efficient Gold-Catalyzed Photoredox α-C(sp³)H Alkynylation of Tertiary Aliphatic Amines with Sunlight
  作者：Jin Xie、Shuai Shi、Tuo Zhang、Nina Mehrkens、Matthias Rudolph、A. Stephen K. Hashmi

  DOI：10.1002/anie.201412399

  日期：2015.5.11

  A new α‐C(sp3)H alkynylation of unactivated tertiary aliphatic amines with 1‐iodoalkynes as radical alkynylating reagents in the presence of [Au2(μ‐dppm)2]2+ in sunlight provides propargylic amines. Based on mechanistic studies, a CC coupling of an α‐aminoalkyl radical and an alkynyl radical is proposed for the C(sp3)C(sp) bond formation. The mild, convenient, efficient, and highly selective C(sp3)H

  一个新的α-C（SP 3） H带1-iodoalkynes如[金存在下进行自由基alkynylating试剂未活化的脂肪族叔胺的炔基2（μ-DPPM）2 ] 2+在太阳光提供丙炔胺。基于机理研究，提出了α-氨基烷基自由基和炔基自由基的CC偶合，以形成C（sp 3）C（sp）键。温和，方便，高效且高度选择性的C（sp 3）炔基化反应显示出优异的区域选择性和良好的官能团相容性。将阳光用作清洁，可持续的能源，可以放大到克量。
• [EN] (METH)ACRYLOXY-CONTAINING TRISILOXANE, SILOXANE-CONTAINING POLYMERS AND BIOMEDICAL DEVICES THEREFROM<br/>[FR] TRISILOXANE CONTENANT UN (MÉTH)ACRYLOXY, POLYMÈRES CONTENANT UN SILOXANE ET DISPOSITIFS BIOMÉDICAUX LES CONTENANT
  申请人：MOMENTIVE PERFORMANCE MAT INC

  公开号：WO2014123956A1

  公开（公告）日：2014-08-14

  There is provided a trisiloxane having a 3-(meth)acryloxy-substituted (hydroxylcyclohexyl)ethyl group, useful in making water absorbing silicone-hydrogel films for biomedical devices, such as contact lens, and a process for producing these monomers. This invention also provides for copolymers made from the trisiloxane having a 3-(meth)acryloxy-substituted (hydroxylcyclohexyl)ethyl group described herein.

  提供了一种三硅氧烷，其具有3-(甲基)丙烯氧基取代的(羟基环己基)乙基基团，可用于制备用于生物医疗器械（如隐形眼镜）的吸水硅烷凝胶膜，并提供了制备这些单体的方法。本发明还提供了由所述具有3-(甲基)丙烯氧基取代的(羟基环己基)乙基基团的三硅氧烷制成的共聚物。
• N-alkylation of ethylenediamine with alcohols catalyzed by CuO-NiO/γ-Al2O3
  作者：Jia-Min Huang、Lu-Feng Xu、Chao Qian、Xin-Zhi Chen

  DOI：10.2478/s11696-012-0140-8

  日期：2012.1.1

  A simple method for N-alkylation of 1,2-diaminoethane with different alcohols in a fixed-bed reactor using cheap CuO-NiO/γ-Al2O3 as the catalyst has been developed. The present catalytic system was applicable in the N-alkylation of 1,2-diaminoethane with both primary and secondary alcohols. Mono-N-alkylation of 1,2-diaminoethane with low-carbon alcohols resulted in high yields; the yields of tetra-N-alkylation of 1,2-diaminoethane with low-carbon alcohols declined markedly with the increase of the molecular volume of alcohols.

  摘要：已开发了一种简单的方法，使用廉价的CuO-NiO/γ-Al2O3作为催化剂，在固定床反应器中将1,2-二氨基乙烷与不同醇类进行N-烷基化。目前的催化系统适用于1,2-二氨基乙烷与一次和二次醇的N-烷基化。1,2-二氨基乙烷与低碳醇类的单N-烷基化产率较高；1,2-二氨基乙烷与低碳醇类的四N-烷基化随着醇类的分子体积增加而显著下降。
• Activation of chlorobenzene with Ni(0) <i>N</i>,<i>N</i>-chelates — A remarkably profound effect of a minuscule change in ligand structure
  作者：William J Marshall、Vladimir V Grushin

  DOI：10.1139/v05-022

  日期：2005.6.1

  Activation of the C—Cl bond of chlorbenzene with [(COD)₂Ni] and a bidentate N,N-ligand such as N,N,N′,N′-tetramethylethylenediamine (tmeda) and 2,2′-bipyridyl (bipy) has been reported to produce σ-phenyl complexes [(tmeda)Ni(Ph)Cl] (1) and [(bipy)Ni(Ph)Cl], respectively. However, in sharp contrast, we found that similar reactions involving almost the identical ligands N,N,N′,N′-tetraethylethylenediamine (teeda) and 6,6′-dimethyl-2,2′-bipyridyl (6,6′-Me₂bipy) resulted in homocoupling and the formation of non-organometallic dichlorocomplexes [(teeda)NiCl₂] and [(6,6′-Me₂bipy)NiCl₂]. The latter two compounds and 1 were characterized by single-crystal X-ray diffraction data. The remarkable change in the reaction outcome points to its extremely high sensitivity to minor alterations in the structure of the stabilizing N,N-ligand. In contrast, analogous reactions of [Pd(dba)₂] with PhI in the presence of teeda or 1,2-dipiperidinoethane (dpe) produced the expected σ-phenyl complexes [(teeda)Pd(Ph)I] and [(dpe)Pd(Ph)I], much like the previously reported reaction with tmeda.Key words: C-Cl activation, zerovalent nickel complexes, N,N-ligands, oxidative addition, homocoupling, X-ray analysis.

  氯苯的C-Cl键与[(COD)₂Ni]和双齿N,N-配体（如N,N,N′,N′-四甲基乙二胺（tmeda）和2,2′-联吡啶（bipy））的活化已被报道，产生σ-苯基配合物[(tmeda)Ni(Ph)Cl]（1）和[(bipy)Ni(Ph)Cl]。然而，与之形成鲜明对比的是，我们发现类似反应涉及几乎相同的配体N,N,N′,N′-四乙基乙二胺（teeda）和6,6′-二甲基-2,2′-联吡啶（6,6′-Me₂bipy）导致同偶联和非有机金属二氯化物配合物[(teeda)NiCl₂]和[(6,6′-Me₂bipy)NiCl₂]的形成。后两种化合物和1通过单晶X射线衍射数据进行了表征。反应结果的显著变化表明其对N,N-配体稳定结构中微小变化的极高敏感性。相比之下，[Pd(dba)₂]与PhI在teeda或1,2-二哌啶乙烷（dpe）存在的情况下的类似反应产生了预期的σ-苯基配合物[(teeda)Pd(Ph)I]和[(dpe)Pd(Ph)I]，类似于先前报道的与tmeda的反应。关键词：C-Cl活化，零价镍配合物，N,N-配体，氧化加成，同偶联，X射线分析。