N-mesitylpivalimidoyl chloride | 208585-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-mesitylpivalimidoyl chloride
• 英文别名: (1Z)-2,2-Dimethyl-N-(2,4,6-trimethylphenyl)propanimidoyl chloride；2,2-dimethyl-N-(2,4,6-trimethylphenyl)propanimidoyl chloride
• CAS: 208585-36-8
• 化学式: C₁₄H₂₀ClN
• 分子量: 237.772
• InChiKey: BDBVTJCRHQZJRI-UHFFFAOYSA-N

物化性质

• 沸点：
  338.6±52.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-mesitylpivalimidoyl chloride 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (Z)-N-(2,2-dimethyl-1-(piperidin-1-yl)propylidene)-2,4,6-trimethylaniline
  参考文献：
  名称：

  Base-Stabilized Nitrilium Ions as Convenient Imine Synthons

  摘要：

  A simple and efficient methodology is presented for the synthesis of a wide range of substituted imines. It is based on stabilizing readily available, but thermally labile, N-alkylnitrilium triflates with pyridine or DMAP to moderately air-stable adducts. These base-stabilized imine synthons react conveniently with phosphorus- and nitrogen-based nucleophiles to amidines and phosphaamidines.

  DOI：

  10.1021/acs.orglett.5b00339
• 作为产物：
  描述：

  N-mesitylphenylpivalamide 在 氯化亚砜 作用下， 反应 2.5h， 以99%的产率得到N-mesitylpivalimidoyl chloride
  参考文献：
  名称：

  硝化离子作为亚胺合成子，可轻松合成磷酸pha和氨基甲酸酯

  摘要：

  易于获得的腈三氟甲磺酸盐是方便的亚胺结构单元，可方便地合成新型1,3-P，N配体，如与伯膦反应所证明的那样。该程序允许所有取代基的变化。报道了硝酸根离子，磷idine和三种磷酰胺盐配合物的X射线晶体结构。磷酰胺酸锂是N配位的，它与[AuCl（tht）]（tht =四氢噻吩）的反应产生独特的P桥金三聚体，而P，N呈双齿状的络合物则来自[{RhCl（cod）} 2 ]。腈离子方法可将1,3-P，N动机扩展为双（亚氨基）膦，双（亚氨基）膦是有价值的β-二酮基配体的中性磷类似物。

  DOI：

  10.1002/anie.201405027

文献信息

• A diamidinatogermylene as a Z-type ligand in a nickel(0) complex
  作者：Zhongtao Feng、Yixiao Jiang、Huapeng Ruan、Yue Zhao、Gengwen Tan、Li Zhang、Xinping Wang

  DOI：10.1039/c9dt03803e

  日期：——

  phosphine functionalized chlorogermylene 1 with Ni(COD)2 (COD = 1,5-cyclooctadiene) afforded the bis-chlorogermylene ligated nickel(0) complex 2 in high yield. The dechlorination reaction of 2 with elemental potassium serendipitously yielded the diamidinatogermylene nickel(0) complex 3. Single-crystal X-ray diffraction analysis reveals that the germanium center in 3 features a pyramidalized geometry, suggesting

  膦官能化的氯亚二甲基亚甲基1与Ni（COD）2（COD ＝ 1，5-环辛二烯）的反应以高收率提供了双氯亚锗基连接的镍（0）配合物2。2与元素钾的脱氯反应偶发，生成了二氨基亚丁二烯镍（0）络合物3。单晶X射线衍射分析表明，在锗中心3设有几何pyramidalized，表明在锗烯基部分3只充当Z型配体，其是通过理论计算进一步支持。配合物3代表带有Z型二氨基亚锗烯配体的第一个实例。
• Synthesis and attempted reductions of bulky 1,3,5-triazapentadienyl groups 2 and 13 halide complexes
  作者：Indrek Pernik、Brant J. Maitland、Andreas Stasch、Cameron Jones

  DOI：10.1139/cjc-2017-0548

  日期：2018.6

  Three extremely bulky 1,3,5-triazapentadienes, ^ArNNNH (^ArNNN = NC(Bu^t)=N(Ar)}₂; Ar = Mes (mesityl), Dep (2,6-diethylphenyl), or Dip (2,6-diisopropylphenyl)) have been prepared and structurally characterized. These are readily deprotonated, yielding a series of lithium and potassium triazapentadienyl complexes, one of which, (^DipNNN)Li, has been structurally characterized. Similarly, three monomeric triazapentadienyl magnesium iodide complexes, (^ArNNN)MgI(OEt₂), and a dimeric calcium counterpart, (^MesNNN)Ca(THF)(μ-I)}₂, have been prepared. Attempts to reduce the former gave homoleptic bis(triazapentadienyl) magnesium complexes, (^ArNNN)₂Mg (Ar = Mes or Dep) as the main products. One reaction also gave a very low yield of the magnesium(I) dimer, (^DepNNN)Mg–}₂, which was structurally characterized. In related chemistry, two triazapentadienyl boron difluoride compounds, (^ArNNN)BF₂ (Ar = Mes or Dep), have been synthesized, and unsuccessful attempts have been made to reduce these to boron(I) heterocycles. For sake of comparison, attempts have been made to prepare a series of related amino-substituted β-diketiminato group 13 element(I) heterocycles. Although these were also not successful, several group 13 element(III) halide complexes incorporating this ligand class have been characterized.

  我们制备了三种极其笨重的 1,3,5-三氮杂戊二烯 ArNNNH（ArNNN = NC(But)=N(Ar)}2; Ar = Mes（甲苯甲基）、Dep（2,6-二乙基苯基）或 Dip（2,6-二异丙基苯基）），并对其进行了结构表征。这些化合物很容易去质子化，产生一系列三氮杂并五二烯锂和钾络合物，其中的 (DipNNN)Li 已具有结构特征。同样，我们还制备了三种单体三氮杂戊二烯基碘化镁络合物 (ArNNN)MgI(OEt2) 和一种二聚钙对应物 (MesNNN)Ca(THF)(μ-I)}2 。尝试还原前者的主要产物是同色的双（三氮杂戊二烯）镁络合物 (ArNNN)2Mg（Ar = Mes 或 Dep）。其中一个反应还得到了产量极低的镁(I)二聚体(DepNNN)Mg-}2，并对其进行了结构表征。在相关的化学反应中，人们合成了两种三氮杂戊二烯基二氟化硼化合物 (ArNNN)BF2 （Ar = Mes 或 Dep），并尝试将它们还原成硼（I）杂环，但均未成功。为了进行比较，还尝试制备了一系列相关的氨基取代的 β-二酮亚甲基 13 族元素（I）杂环。虽然这些尝试也没有取得成功，但有几种含有该配体类别的第 13 族元素（III）卤化物配合物已经定性。
• Synthesis, structure, and properties of magnesium complexes containing cyclopentadienyl and amidinate ligand sets
  作者：Aibing Xia、Hani M El-Kaderi、Mary Jane Heeg、Charles H Winter

  DOI：10.1016/s0022-328x(03)00787-3

  日期：2003.10

  N,N'-Bis(2,6-diisopropylphenyl)(tert-butyl)amidine and N,N'-bis(2,4,6-trimethyl-phenyl)(tert-butyl)amidine were prepared and treated with [CpMgMe(Et2O)](2) in diethyl ether or tetrahydrofuran to afford the monomeric amidinate complexes [CpMg(eta(2)-(BuC)-Bu-t(N(2,6-(Pr2C6H3)-Pr-i))(2))] (87%) and [CpMg(eta2-(BuC)-Bu-t(N(2,4,6-Me3C6H2))(2))(THF)] (76%). The solid-state structures of the amidines and resultant magnesium complexes were determined by X-ray diffraction methods. In the solid-state, the magnesium complexes are monomeric and contain one eta(5)-cyclopentadienyl ligand and one eta(2)-amidinate ligand, as well as one tetrahydrofuran ligand for the latter. [CpMg(eta(2)-(BuC)-Bu-t(N(2,6-(Pr2C6H3)-Pr-i))(2))] can be sublimed unchanged with 80% recovery at 180 degreesC/0.05 torr, while [CpMg(eta(2)-(BuC)-Bu-t(N(2,4,6-Me3C6H2))(2))(THF)] decomposes to Cp2Mg (77%) and [Mg(eta(2)-(BuC)-Bu-t(N(2,4,6-Me3C6H2)))(2)] (83%) under similar conditions. [Mg(eta(2)-(BuC)-Bu-t(N(2,4,6-Me3C6H2)))(2)] was prepared independently through treatment of dibutylmagnesium with two equivalents of N,N'-bis(2,4,6-trimethylphenyl)(tert-butyl)amidine in toluene at ambient temperature. (C) 2003 Elsevier B.V. All rights reserved.
• Facile Synthesis of Phosphaamidines and Phosphaamidinates using Nitrilium Ions as an Imine Synthon
  作者：Tom van Dijk、Sebastian Burck、Mark K. Rong、Amos J. Rosenthal、Martin Nieger、J. Chris Slootweg、Koop Lammertsma

  DOI：10.1002/anie.201405027

  日期：2014.8.18

  Readily accessible nitrilium triflates are convenient imine building blocks for the expedient synthesis of a novel class of 1,3‐P,N ligands as demonstrated for the reaction with primary phosphanes. This procedure allows variation of all substituents. X‐ray crystal structures are reported for nitrilium ions, phosphaamidines, and three phosphaamidinate complexes. The lithium phosphaamidinate is N coordinated

  易于获得的腈三氟甲磺酸盐是方便的亚胺结构单元，可方便地合成新型1,3-P，N配体，如与伯膦反应所证明的那样。该程序允许所有取代基的变化。报道了硝酸根离子，磷idine和三种磷酰胺盐配合物的X射线晶体结构。磷酰胺酸锂是N配位的，它与[AuCl（tht）]（tht =四氢噻吩）的反应产生独特的P桥金三聚体，而P，N呈双齿状的络合物则来自[RhCl（cod）} 2 ]。腈离子方法可将1,3-P，N动机扩展为双（亚氨基）膦，双（亚氨基）膦是有价值的β-二酮基配体的中性磷类似物。
• Base-Stabilized Nitrilium Ions as Convenient Imine Synthons
  作者：Tom van Dijk、Martijn S. Bakker、Flip Holtrop、Martin Nieger、J. Chris Slootweg、Koop Lammertsma

  DOI：10.1021/acs.orglett.5b00339

  日期：2015.3.20

  A simple and efficient methodology is presented for the synthesis of a wide range of substituted imines. It is based on stabilizing readily available, but thermally labile, N-alkylnitrilium triflates with pyridine or DMAP to moderately air-stable adducts. These base-stabilized imine synthons react conveniently with phosphorus- and nitrogen-based nucleophiles to amidines and phosphaamidines.