C-mesityl-N-methylnitrone

• 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: C-mesityl-N-methylnitrone
• 英文别名: N-methyl-1-(2,4,6-trimethylphenyl)methanimine oxide
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: QUPJCNAAUMBYDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  C-mesityl-N-methylnitrone 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以65%的产率得到N,2,4,6-tetramethylbenzamide
  参考文献：
  名称：

  使用亚硝基连续流光化学重排进行肽片段偶联

  摘要：

  顺其自然通过被描述硝酮的连续流动光化学重排的方式（参见方案）用于酰胺键形成的一般方法：。简单的芳基-烷基酰胺键以及复杂的肽键可在不到20分钟的停留时间内高效构建。用这种方法合成了四肽，该方法可用于肽片段的偶联。

  DOI：

  10.1002/anie.201300504
• 作为产物：
  描述：

  2,4,6-三甲基苯甲醛 、 N-甲基羟胺盐酸盐 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 22.0h， 以98%的产率得到C-mesityl-N-methylnitrone
  参考文献：
  名称：

  路易斯酸对C-芳基醛酮与烯烃的1,3-偶极环加成反应的影响。

  摘要：

  发现路易斯酸对C-芳基-N-烷基醛酮（1a-e）与某些烯烃的1，3-偶极环加成反应的区域选择性和立体选择性具有显着影响。反应速度也受添加路易斯酸的影响。在使用烯丙醇作为双极性亲和剂的反应中，添加路易斯酸会显着加快反应速度，并极大地改变立体选择性。在使用丙烯酸乙酯作为双极性亲和剂的反应中，无论反应是在存在或不存在路易斯酸的条件下进行的，区域选择性都是相反的。即，异恶唑烷-5-羧酸盐主要在没有路易斯酸的情况下获得，尽管异恶唑烷-4-羧酸盐主要在路易斯酸的存在下获得。当C，N-二芳基醛酮（1k，1m，

  DOI：

  10.1248/cpb.50.908
• 作为试剂：
  描述：

  1,3-茚满二酮 、 丙酮 在 C-mesityl-N-methylnitrone 作用下， 反应 2.0h， 以77%的产率得到2-(propan-2-ylidene)-1H-indene-1,3(2H)-dione
  参考文献：
  名称：

  Solvent-dependent reactivities of acyclic nitrones with β-diketones: catalyst-free syntheses of endiones and enones

  摘要：

  Reactions of the nitrones -O+N(Me)=C(H)Ar 1 (Ar=phenyl 1a, 4-methylphenyl 1b, 2,4,6-trimethylphenyl 1c, and anthracen-9-yl 1d) with the cyclic beta-diketones 1,3-indandione 2 or barbituric acid 3 in CH2Cl2, afford the corresponding endiones 2'a-2'd or 3'a-3'd. In contrast, dimedone 4 reacts with 1a or 1b to give the endione 4'a or 4'b and the bis-adduct 4 '' a or 4 '' h. Nevertheless, reaction of 4 with 1c or 1d in CH2Cl2 furnishes only the endione adducts 4'c or 4'd. However, the reaction of 4 with 1a or 1b in methanol gives only 4 '' a or 4 '' b, respectively. Among acyclic beta-diketones only malonic acid 7 reacts with 1a-1c. Reaction of 7 with 1a in CH2Cl2 forms cinnamic acid 7 '' a, whereas in the case of 1b, the endione 7'b and (E)-3-p-tolylacrylic acid 7 '' b are obtained. The nitrone 1c reacts with 7 in CH2Cl2 to afford the endione 7'c or with acetone yielding (E)-4-mesitylbut-3-en-2-one 8. X-ray analyses are reported for 4'c, 5, and 7 '' b. In addition, the calculated acidity of the hydrogen at the alpha-C atom is shown to correlate with the reactivity of the beta-diketones with nitrones. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.086

文献信息

• Optically Active Mixed Unsymmetric Imine Platinum(II) Complexes – Utilization of the Liberated Imines for Further Syntheses of Mixed Imine‐Diazadiene Complexes and of ( <i>E</i> )‐Cyanoalkenes
  作者：Jamal Lasri、M. Fátima C. Guedes da Silva、M. Adília Januário Charmier、Armando J. L. Pombeiro

  DOI：10.1002/ejic.200800343

  日期：2008.8

  in better yields (71-50%), the same products. The new optically active diimine compounds NH=C(R)ON=C-(CgH 16 ) (8) are quantitatively liberated upon reaction of complexes 7 with a diphosphane. The chiral diimino ester 8a (R = CH 2 CO 2 Me) acts as a protic nucleophile and efficiently couples with the coordinated nitrile in 4 to give the new optically active, mixed, unsymmetric imine-1,3-diaza-1,3-diene

  用 (R*)-樟脑肟 (C 9 H 16 )C=NOH (R*) 处理反式-[PtC1 2 (NCR) 2 ] (1) R = CH 2 CO 2 Me (la), Ph (1b)} ( 2) 获得旋光混合亚胺-腈络合物反式-(R*)-[PtCl 2 NH=C(R)ON=C(C 9 H 16 )}(NCR)] (4)，其中，与酮肟反应 R 1 R 2 C=NOH (3) R 1 =R 2 = Me (3a), C 4 H 8 (3b)}，得到手性不对称双（亚胺）配合物反式（R*） -[PtCl 2 NH=C(R)ON=C(C9Hi6)}NH=C(R)-ON=CR 1 R 2 }] (6) 中等收率。另一种途径涉及起始配合物 1 与酮肟 3 反应得到混合亚胺-腈配合物反式-[PtCl 2 NH=C(R)ON=CR 1 R 2 }(NCR)] (5)，然后通过后者与 (R*)-樟脑肟
• Palladium(II)-assisted [2+3] cycloaddition of nitrones to organonitriles: Synthesis of 2,3-dihydropyrrolo[1,2-a]quinazolin-5-one and Δ4-1,2,4-oxadiazoline derivatives
  作者：Jamal Lasri

  DOI：10.1016/j.poly.2013.04.017

  日期：2013.7

  The [2+3] cycloadditions of different organonitriles NCR (R1 = C6F5, R2 = Pr, R3 = p-CHOC6H4, R4 = Ph) with the cyclic nitrone or acyclic nitrone −O+N(Me)C(H)(C6H2Me3-2,4,6), in the presence of PdCl2, give the corresponding fused tricyclic fluorinated ketoimine trans- (1), fused bicyclic Δ4-1,2,4-oxadiazoline trans- (R2 = Pr (2), R3 = p-CHOC6H4 (3)) or monocyclic Δ4-1,2,4-oxadiazoline trans- (4) palladium(II)

  的[2 + 3]不同有机腈的环加成NCR（R 1  = C 6 ˚F 5，R 2  = PR，R 3  =  p -CHOC 6 ħ 4，R 4  =苯基）与环状硝酮或无环硝酮- Ò + N（Me）的C（H）（C 6 H ^ 2我3 -2,4,6-），在的PdCl存在2，得到相应的稠合的三环的氟化酮亚胺反式- （1），稠合的二环Δ 4 -1， 2,4-恶二唑啉反式-（R 2 = PR（2）中，R 3  =  p -CHOC 6 ħ 4（3））或单环Δ 4 -1,2,4-恶二唑啉的反式- （4）钯（II）络合物。的自由四氟-2,3-二氢吡咯并[1,2-A]喹唑啉-5-酮（1A）和Δ 4 -1,2,4-恶二唑啉（2A -图4a）的后配合物的反应中释放1 - 4与二膦（dppe）。所有化合物均通过元素分析，ESI + -MS，IR，1 H和13进行表征13 C NMR光谱学。
• Pt^II-Mediated Imine–Nitrile Coupling Leading to Symmetrical (1,3,5,7,9-Pentaazanona-1,3,6,8-tetraenato)Pt(II) Complexes Containing the Incorporated 1,3-Diiminoisoindoline Moiety
  作者：Jamal Lasri、Maxim L. Kuznetsov、M. Fátima C. Guedes da Silva、Armando J. L. Pombeiro

  DOI：10.1021/ic301176b

  日期：2012.10.15

  Treatment of trans-[PtCl2(NCR)(2)] (1; R = Et (1a), Ph (1b)) with 1,3-diiminoisoindoline (2) gives access to the corresponding symmetrical (1,3,5,7,9-pentaazanona-1,3,6,8-tetraenato)Pt(II) complexes [PtClNH=C(R)N=C(C6H4)-NC=NC(R)=NH}] (3). The reactions of 1 with one equivalent of 1,1,3,3-tetramethylguanidine (4), 1,3-diphenylguanidine (6), or acetone oxime (8) leads to the formation of mixed asymmetrical Pt(II) complexes trans-[PtCl2NH=C(R)N=C(NMe2)(2)} (NCR)] (5), [PtClNH=C(R)NC(NHPh)=NPh}(NCR)] (7), or trans-[PtCl2NH=C(Ph)ON=CMe2)(NCPh)] (9), respectively, as a result of nucleophilic addition to one of the nitrile ligands in I. Treatment of 5, 7, and 9 with one equivalent of 2 leads to complexes 3. The complexes were characterized by IR. H-1, C-13H-1}, and Pt-195 NMR (for 3) spectroscopies, ESI+-MS, elemental analyses, and X-ray diffraction (for 3). Complex 3a has an asymmetric unit with five independent Pt molecules of the same chemical composition and two molecules of water, resulting in a total of 40 molecules of the complex and sixteen guest water molecules per unit cell. Theoretical calculations revealed that the most plausible mechanism of formation of complexes 3 includes stepwise nucleophilic addition of 2 to one of the nitrile ligands in 1, a first cyclization upon formation of the Pt-N bond and elimination of HCl, and a second nucleophilic addition/cyclization.