3-methylsalicylanil | 86010-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-methylsalicylanil
• 英文别名: N-(3-methylsalicylidene)aniline；N-phenyl-3-methylsalicylaldimine；HOC6H3(Me)CHNPh；3-Methylsalicylidenanilin；2-methyl-6-(phenyliminomethyl)phenol
• CAS: 86010-97-1
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: VMEPTHKTVFRAAW-UHFFFAOYSA-N

物化性质

• 熔点：
  74 °C
• 沸点：
  359.7±35.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methylsalicylanil 在 硫酸 作用下， 反应 2.0h， 以45%的产率得到N-phenyl-3-methylsalicylaldimine-5-sulfonic acid
  参考文献：
  名称：

  磺酸盐取代的席夫碱配体的水溶性diMn III配合物的合成，表征和过氧化氢酶活性：H 2 O 2歧化的高效催化剂

  摘要：

  一种新的diMn III络合物Na [Mn 2（3-Me-5-SO 3 -salpentO）（μ-MeO）（μ-AcO）（H 2 O）]·4H 2 O（1），其中salpentOH = 1合成了5-5-双（水杨酰氨基）戊丹-3-醇并对其结构进行了表征。该配合物具有双（μ-烷氧基）（μ-乙酰基）三桥联的二锰III核，其结构在溶解时得以保留。络合物1在pH≥8.5的水溶液或DMF中使H 2 O 2歧化的效率很高，但活性仅略有下降。电喷雾电离质谱，EPR和紫外可见光谱法用于监测H 2 O2在缓冲的碱性介质中的歧化，表明循环过程中催化剂的主要活性形式以Mn III 2氧化态发生，并且起始配合物保留了催化过程中的双核和组成，其中乙酸盐从桥联过渡到末端配体。UV-vis和h的拉曼光谱2 ö 2 + 1 +卜4的DMF NOH混合物表明，催化周期涉及的Mn III 2 / Mn为IV 2的氧化水平。在pH

  DOI：

  10.1021/ic2011452
• 作为产物：
  描述：

  2-羟基-3-甲基苯甲醛 、 苯胺 在 3 A molecular sieve 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 3-methylsalicylanil
  参考文献：
  名称：

  用于烯烃聚合的具有两个苯氧基-亚胺螯合配体的锆配合物家族

  摘要：

  发现具有两个苯氧基-亚胺螯合配体双[N-(3-叔丁基水杨亚基)anilinato]锆(IV)二氯化物(1)的锆配合物显示出非常高的乙烯聚合活性，为550 kg聚合物/mmol使用甲基铝氧烷 (MAO) 作为助催化剂，在 25 °C 和大气压下，cat·h 的粘均分子量 (Mv) 值为 0.9 × 104。在相同聚合条件下，这种活性比 Cp2ZrCl2 表现出的活性高 1 个数量级。使用 Ph3CB(C6F5)4/i-Bu3Al 代替 MAO 作为助催化剂产生极高分子量的聚乙烯，Mv 505 × 104，在 50 °C 下的活性为 11 kg 聚合物/mmol cat·h . 该 Mv 值是均相烯烃聚合催化剂显示的最高值之​​一。配合物 1，使用 Ph3CB(C6F5)4/i-Bu3Al 作为助催化剂，提供了一种高分子量乙烯-丙烯共聚物，Mv 109 × 104，在丙烯含量为 20.7 mol%

  DOI：

  10.1021/ja0032780

文献信息

• Zinc(II) Homogeneous and Heterogeneous Species and Their Application for the Ring‐Opening Polymerisation of <i>rac</i> ‐Lactide
  作者：Matthew D. Jones、Matthew G. Davidson、Callum G. Keir、Laura M. Hughes、Mary F. Mahon、David C. Apperley

  DOI：10.1002/ejic.200801049

  日期：2009.2

  motif was detected. The Schiff base ligand L1H was anchored to silica and treated with Zn(OAc)2·2H2O to form the heterogeneous ZnII system. This was characterised by 13C1H} CP/MAS NMR spectroscopy. All homogeneous and heterogeneous catalysts were assessed for the ring-opening polymerisation of rac-lactide at 130 °C in the absence of solvent, using unsublimed monomer. All catalysts offered good conversions

  席夫碱配体 (L1H–L8H) 已制备并与 ZnII 中心络合。所有八种配合物都通过单晶 X 射线衍射方法、多核 NMR 光谱和元素分析进行​​了表征。结果表明，分离出 Zn3(OAc)4(L1-2)2 形式的 L1H 和 L2H 三金属配合物。然而，对于形成 L3H 到 L7H 的单金属配合物，Zn(L3-7)2。对于 L8H，也分离出与 Zn3(OAc)4(L1-2)2 具有相同化学计量的三金属配合物，但检测到不同的配位基序。席夫碱配体 L1H 被固定在二氧化硅上并用 Zn(OAc)2·2H2O 处理形成非均相 ZnII 系统。这通过 13 C1H} CP/MAS NMR 光谱表征。使用未升华的单体，在没有溶剂的情况下，在 130°C 下评估所有均相和非均相催化剂的外消旋丙交酯的开环聚合反应。所有催化剂都提供了良好的转化率和中等程度的控制。（© Wiley-VCH Verlag GmbH
• Synthesis of <i>gem</i>-Difluorinated 2,3-Dihydrobenzofurans Using Freon-22 via [4 + 1] Annulation of Difluorocarbene and Antitumor Activity Evaluation
  作者：Qianying Zhou、Mi Huang、Yongcun Shen、Zhenling Chen、Liying Xu、Zhigang Yang

  DOI：10.1021/acs.orglett.4c00011

  日期：2024.2.16

  efficient assembly of valuable fluorinated 2,3-dihydrobenzofurans from the [4 + 1] annulation in good yields under basic conditions. The reliable practicability and scalability of the process have also been demonstrated by preparation at the multigram scale, late-stage modifications of pharmaceutical molecules, and potential antitumor potency.

  作为一种廉价的工业化学品，二氟氯甲烷(Freon-22)尽管其反应性相对较低，但可以作为构建宝石二氟化环结构的实用CF 2源。在这里，我们开发了一种在基本条件下以良好产率从 [4 + 1] 环化有效组装有价值的氟化 2,3-二氢苯并呋喃的方案。数克规模的制备、药物分子的后期修饰以及潜在的抗肿瘤效力也证明了该工艺的可靠实用性和可扩展性。
• Insight into the Steric and Electronic Effects of Ancillary Ligands: Synthesis and Structure−Reactivity Relationship of Well-Defined, Air- and Moisture-Stable (NHC)Pd(sal)Cl Complexes (sal = Salicylaldimine)
  作者：Zhong Jin、Ling-Ling Qiu、Yan-Qing Li、Hai-Bin Song、Jian-Xin Fang

  DOI：10.1021/om100906n

  日期：2010.12.13

  Synthesis of a series of (NHC)Pd(sal)Cl complexes, 1-5, bearing a salicylaldimine (sal) unit was described. The structure reactivity relationship, especially the steric and electronic effects of the salicylaldimine ligands on their catalytic activities, was investigated intensively in the Buchwald-Hartwig coupling reaction. Our study demonstrated that the sterically encumbered N-aryl groups in the salicylaldimine unit give rise to an obviously negative effect in the aryl amination reaction. Additionally, incorporating a steric substituent into the ortho-position of the phenoxide oxygen atom does not appear to be beneficial to their catalytic activity. Notably, the electronic nature of N-substituted aryl groups in the salicylaldimine ligands plays a significant role in their catalytic activities. An electron-rich N-aryl group causes an obviously decreasing yield, while an electron-deficient one, such as complex 5b, leads to enhanced reactivity. The aryl amination reaction with complex 5b was also found to be remarkably tolerant to both air and moisture. Under optimized reaction conditions, a range of aryl chlorides and amines could be coupled smoothly under aerobic conditions.
• Ethylene and propylene polymerization behavior of a series of bis(phenoxy–imine)titanium complexes
  作者：Rieko Furuyama、Junji Saito、Sei-ichi Ishii、Makoto Mitani、Shigekazu Matsui、Yasushi Tohi、Haruyuki Makio、Naoto Matsukawa、Hidetsugu Tanaka、Terunori Fujita

  DOI：10.1016/s1381-1169(03)00096-7

  日期：2003.6

  This contribution reports ethylene and propylene polymerization behavior of a series of Ti complexes bearing a pair of phenoxy-imine chelate ligands. The bis(phenoxy-imine)Ti complexes in conjunction with methylalumoxane (MAO) can be active catalysts for the polymerization of ethylene. Unexpectedly, this C-2 symmetric catalyst produces syndiotactic polypropylene. C-13 NMR spectroscopy has revealed that the syndiotacticity arises from a chain-end control mechanism. Substitutions on the phenoxy-imine ligands have substantial effects on both ethylene and propylene polymerization behavior of the complexes. In particular, the steric bulk of the substituent ortho to the phenoxy-oxygen is fundamental to obtaining high activity and high molecular weight for ethylene polymerization and high syndioselectivity for the chain-end controlled propylene polymerization. The highest ethylene polymerization activity, 3240 kg/mol-cat h, exhibited by a complex having a t-butyl group ortho to the phenoxy-oxygen, represents one of the highest reported to date for Ti-based non-metallocene catalysts. Additionally, the polypropylene produced exhibits a T-m, 140degreesC, and syndioselectivity, rrrr 83.7% (achieved by a complex bearing a trimethylsilyl group ortho to the phenoxy-oxygen) that are among the highest for polypropylenes produced via a chain-end control mechanism. Hence, the bis(phenoxy-imine)Ti complexes are rare examples of non-metallocene catalysts that are useful for the polymerization of not only ethylene but also propylene. (C) 2003 Elsevier Science B.V. All rights reserved.