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.
• The Effects of Lewis Acid on the 1,3-Dipolar Cycloaddition Reaction of C-Arylaldonitrones with Alkenes.
  作者：Tomio Shimizu、Masaya Ishizaki、Nobuo Nitada

  DOI：10.1248/cpb.50.908

  日期：——

  The regio- and stereoselectivity of the 1,3-dipolar cycloaddition reactions of C-aryl-N-alkylaldonitrones (1a-e) with some alkenes were found to be affected significantly by the addition of Lewis acid. The rate of the reaction was also affected by adding the Lewis acid. In the reactions using allyl alcohol as a dipolarophile an addition of Lewis acid caused a remarkable acceleration of the reaction

  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，
• Peptide Fragment Coupling Using a Continuous-Flow Photochemical Rearrangement of Nitrones
  作者：Yuan Zhang、Melissa L. Blackman、Andrew B. Leduc、Timothy F. Jamison

  DOI：10.1002/anie.201300504

  日期：2013.4.8

  amide bond formation by way of a continuous‐flow photochemical rearrangement of nitrones was described (see scheme). Simple aryl‐alkyl amide bonds as well as complex peptide bonds were constructed efficiently with a residence time less than 20 minutes. A tetrapeptide was synthesized in this way and the method could be applied to peptide fragment coupling.

  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。