3-叔丁基-2-羟基-6-甲基苯甲醛 | 68591-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-叔丁基-2-羟基-6-甲基苯甲醛
• 英文名称: 2-hydroxy-3-tert-butyl-6-methyl-benzaldehyde
• 英文别名: 3-tert-Butyl-2-hydroxy-6-methylbenzaldehyde
• CAS: 68591-08-2
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: YAGXJTGFNACZEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-叔丁基-2-羟基-6-甲基苯甲醛 在 硝酸 、 sodium acetate 、 溶剂黄146 作用下， 生成 8-叔丁基-5-甲基-6-硝基香豆素
  参考文献：
  名称：

  422.香豆酸的稳定性。羟基螯合

  摘要：

  DOI：

  10.1039/jr9560002155
• 作为产物：
  描述：

  6-叔丁基间甲酚 、 原甲酸三乙酯 生成 3-叔丁基-2-羟基-6-甲基苯甲醛
  参考文献：
  名称：

  Casiraghi,G. et al., Gazzetta Chimica Italiana, 1978, vol. 108, p. 79 - 84

  摘要：

  DOI：

文献信息

• Radical and migratory insertion reaction mechanisms in Schiff base zirconium alkyls
  作者：Paul D. Knight、Guy Clarkson、Max L. Hammond、Brian S. Kimberley、Peter Scott

  DOI：10.1016/j.jorganchem.2005.03.043

  日期：2005.11

  nevertheless transforms an inactive precatalyst into a stable system for the polymerisation of ethene. Closely related unbridged salicylaldimine catalysts are known to be highly active catalysts, but in most cases they appear to suffer from high temperature instability. The first examples of zirconium alkyls of this class are isolated, and it is found that they are inherently much more resistant to decomposition

  2,2'-二氨基-6,6'-二甲基联苯的四个水杨醛亚胺衍生物H 2 L 4–7，其中CN键在苯酚环上的取代基在空间上受到保护，形成锆的烷基，顺式-α-[Zr L 4–7（CH 2 Ph）2 ]。它们不是通过已确定的烷基1,2-迁移插入亚胺的途径分解，而是经历自由基机理。观察到的大量产品，动力学和热力学数据（Rice-Herfeld，3/2阶，正ΔS ‡）证明了这一点。），对空间因素的反应以及切换为不稳定的自由基离去基团会抑制反应的事实。相反，1,2-迁移插入是干净的一阶分子内过程，ΔS ‡为负。然而，配体的空间修饰将惰性的预催化剂转化为用于乙烯聚合的稳定体系。紧密相关的未桥水杨醛亚胺催化剂已知是高活性催化剂，但是在大多数情况下，它们似乎遭受高温不稳定性的困扰。分离了这类锆烷基的第一个实例，发现它们固有地对通过任一途径（迁移插入或自由基）分解的抵抗力强得多。结构研究被用来解释这种行为上的差异
• Chiral biarylamido/anisole complexes of yttrium in enantioselective aminoalkene hydaroamination/cyclisation
  作者：Paul N. O'Shaughnessy、Kevin M. Gillespie、Paul D. Knight、Ian J. Munslow、Peter Scott

  DOI：10.1039/b400799a

  日期：——

  A group of chiral, dibasic, biaryl-bridged amido proligands containing peripheral methoxyphenyl (anisole) ligation are developed for the synthesis of new amide complexes of yttrium and lanthanum. A potentially tetradentate bis(amidoanisole) system L111 gives, on reaction with [YN(SiMe2H)2}3(THF)] a crystallographically-characterised bis complex [YL111(HL111)] presumably as a result of low steric demand, since a more bulky version L222 gives the target [L222YN(SiMe2H)2}(THF)]. The molecular structure of the latter reveals a similar cis-α structure to our recently reported Schiff-base analogue. Variable-temperature NMR studies are consistent with low rigidity in the molecular structure. A potentially tridentate, amidoanisolyl/amido proligand L333 gives complexes [L333MN(SiMe2H)2}(THF)n] (M = Y, n = 1; M = La, n = 2). Chiral non-racemic versions of the above complexes were tested in the hydroamination/cyclisation of 2,2′-dimethylaminopentane to the corresponding pyrrolidine. Activities were relatively low compared to recently reported examples, and ee values were in the range 20–40% despite the well-expressed chirality of the catalysts.

  一组包含外周甲氧基苯（阿尼索尔）配体的手性二元、双芳基桥接酰胺前配体被开发用于合成新的钇及铈的酰胺复合物。一个潜在的四齿双（酰胺阿尼索尔）体系L111与[YN(SiMe2H)2}3(THF)]反应，形成一个结晶学上表征的双配合物[YL111(HL111)]，这可能是由于低立体需求，因为一个更笨重的版本L222则生成目标复合物[L222YN(SiMe2H)2}(THF)]。后者的分子结构显示出与我们最近报道的肼碱类类似的顺式α结构。可变温度NMR研究表明分子结构的刚性较低。一个潜在的三齿酰胺阿尼索尔/酰胺前配体L333生成复合物[L333MN(SiMe2H)2}(THF)n]（M = Y，n = 1；M = La，n = 2）。上述复合物的手性非外消旋版本在2,2′-二甲基氨基戊烷的氢胺化/环化反应中被测试以生成相应的吡咯烷。与最近报道的例子相比，活性相对较低，尽管催化剂表现出良好的手性，ee值仍在20-40%的范围内。
• Group 4 catalysts for ethene polymerization containing tetradentate salicylaldiminato ligands
  作者：Guy J. Clarkson、Vernon C. Gibson、Peter K. Y. Goh、Max L. Hammond、Paul D. Knight、Peter Scott、Theo M. Smit、Andrew J. P. White、David J. Williams

  DOI：10.1039/b610555f

  日期：——

  productivities of multimodal poly(ethene), while in contrast the structurally analogous titanium compounds provide highly active, single site catalysts. Thermal degradation of these catalysts is slowed significantly by a substitution pattern on the phenolate unit which sterically protects the imine donor unit; a phenomenon which has been previously observed in much lower activity catalysts based on 2,2'-diaminobiphenyl

  使用X射线衍射和NMR光谱阐明了三类新的带有四齿水杨基铝亚氨基配体的钛和锆配合物的结构特性。用MAO助催化剂活化后，它们在乙烯聚合中的行为在很大程度上取决于结构的性质和取代方式。一种基于2-氨基苄胺（C3链）主链的钛配合物具有共配体位点的反式排列，并且毫不奇怪，它不会聚合乙烯。1,8-二氨基萘（C3链）骨架具有相当强的环应变顺式配合物，但也无能为力。一系列具有2,2'-二氨基联苄（C6-链）骨架的锆顺式配合物可提供低至中等生产率的多峰聚乙烯。相反，结构类似的钛化合物则提供了高活性的单中心催化剂。这些催化剂的热降解可通过苯酚酸酯单元上的取代模式（在空间上保护亚胺供体单元）而大大减慢；这种现象以前已在基于2，2'-二氨基联苯（C4链）的低得多的催化剂中观察到，但并没有改善非常高活性的未桥联体系的稳定性。
• TERMINALLY MODIFIED POLYBRANCHED POLYIMIDE, METAL-PLATED TERMINALLY MODIFIED POLYBRANCHED POLYIMIDE, AND METHOD FOR PRODUCING THE SAME
  申请人：Ataka Kikuo

  公开号：US20100009206A1

  公开（公告）日：2010-01-14

  A terminally-modified polybranched polyimide which can be efficiently complexed with an inorganic material is obtained by reacting a component (a): tetracarboxylic dianhydride; a component (b): as an amine component, a mixture of a triamine and a diamine (which may be composed of a triamine only); and a component (c): as a terminal component, a compound selected from general formulae (1-1) to (1-4). H 2 N—X—R 1 (1-1) (In the formula, X represents a single bond or an alkylene group having 1 to 3 carbon atoms, and R 1 represents a nitrogen-containing heterocyclic group). H 2 N—X—R 1 (1-2) (In the formula, X is as defined above, and R 1 represents a sulfur-containing heterocyclic group or an aryl group having a thiol or thioether group in the molecule). (In the formula, R represents a nitrogen-containing heterocyclic group). (In the formula, R represents a monovalent residue).

  通过反应组分(a):四羧酸二酐;组分(b):作为胺组分，三胺和二胺的混合物(可以仅由三胺组成);以及组分(c):作为末端组分，从通式(1-1)到(1-4)中选择的化合物，可以获得与无机材料高效络合的终止修饰的多支化聚酰亚胺。 H2N-X-R1(1-1)(式中，X表示单键或具有1到3个碳原子的烷基基团，R1表示含氮杂环基团)。 H2N-X-R1(1-2)(式中，X如上定义，R1表示含硫杂环基团或分子中具有巯基或硫醚基团的芳基基团)。 (式中，R表示含氮杂环基团)。 (式中，R表示单价残基)。
• Antagonists for the Orphan G-Protein-Coupled Receptor GPR55 Based on a Coumarin Scaffold
  作者：Viktor Rempel、Nicole Volz、Franziska Gläser、Martin Nieger、Stefan Bräse、Christa E. Müller

  DOI：10.1021/jm4005175

  日期：2013.6.13

  The orphan G-protein-coupled receptor GPR55, which is activated by 1-lysophosphatidylinositol and interacts with cannabinoid (CB) receptor ligands, has been proposed as a new potential drug target for the treatment of diabetes, Parkinson's disease, neuropathic pain, and cancer. We applied beta-arrestin assays to identify 3-substituted coumarins as a novel class of antagonists and performed an extensive structure-activity relationship study for GPR55. Selectivity versus the related receptors CB1, CB2, and GPR18 was assessed. Among the 7-unsubstituted coumarins selective, competitive GPR55 antagonists were identified, such as 3-(2-hydroxybenzyl)-5-isopropyl-8-methyl-2H-chromen-2-one (12, PSB-SB-489, IC50 = 1.77 mu M, pA(2) = 0.547 mu M). Derivatives with long alkyl chains in position 7 were potent, possibly allosteric GPR55 antagonists which showed ancillary CB receptor affinity. 7-(1,1-Dimethyloctyl)-5-hydroxy-3-(2-hydroxybenzyl)-2H-chromen-2-one (69, PSB-SB-487, IC50 = 0.113 mu M, K-B = 0.561 mu M) and 7-(1,1-dimethylheptyl)-5-hydroxy-3-(2-hydroxybenzyl)-2H-chromen-2-one (67, PSB-SB-1203, IC50 = 0.261 mu M) were the most potent GPR55 antagonists of the present series.