2-hydroxy-3,4,6-trimethylbenzaldehyde | 42374-07-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-3,4,6-trimethylbenzaldehyde
• 英文别名: 2-Hydroxy-3,4,6-trimethylbenzaldehyd；2-formyl-3,5,6-trimethylphenol；2-hydroxy-3,4,6-trimethyl-benzaldehyde；2-Hydroxy-3,4,6-trimethyl-benzaldehyd；6-hydroxy-2,4,5-trimethylbenzaldehyde；6-Hydroxy-2,4,5-trimethyl-benzaldehyd
• CAS: 42374-07-2
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: HMDZYDQJTVRBKN-UHFFFAOYSA-N

物化性质

• 熔点：
  77-78 °C(Solv: ethanol (64-17-5))
• 沸点：
  258.3±35.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-hydroxy-3,4,6-trimethylbenzaldehyde 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl (2,5,7,8-tetramethylchroman-2-yl)acetate
  参考文献：
  名称：

  Solid-phase synthesis: a linker for side-chain anchoring of arginine

  摘要：

  A new linker based on a chroman system is described for the side-chain anchoring of Arg and other guanidine-containing molecules. The system is compatible with the Fmoc/tBu solid-phase strategy, because the release of the final product is achieved by treatment with TFA in the presence of scavengers. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)01203-6
• 作为产物：
  描述：

  1,2,4-三甲基苯 在 盐酸 、 三氯化铝 、 硫酸 、 氨 、 iron(II) sulfate 、 potassium nitrate 、 苯 作用下， 生成 2-hydroxy-3,4,6-trimethylbenzaldehyde
  参考文献：
  名称：

  Gattermann, Justus Liebigs Annalen der Chemie, 1906, vol. 347, p. 353

  摘要：

  DOI：

文献信息

• Sulphonyl compounds for use as linkers in solid phase and combinatorial synthesis
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06225480B1

  公开（公告）日：2001-05-01

  The present invention relates to a linker shown by the following formula (I): X—SO2—R1—(A)m—R2  (I) wherein R1 is a group of the formula (A): [wherein R3, R4 and R5 are the same or different hydrogen, etc], etc, R2 is a group which can form a chemical bond to a resin which may be protected by a conventional protective group, A is lower alkylene, etc, X is a leaving group, and m is an integer of 0 or 1, with proviso that A is (C2-C6)alkylene, and m is an integer of 1, when R1 is a group of the formula (A).

  本发明涉及以下式(I)所示的连接剂： X—SO2—R1—(A)m—R2  (I) 其中R1是式(A)的一个基团： 【其中R3、R4和R5相同或不同为氢等】等， R2是一个可以与树脂形成化学键的基团，该树脂可能由传统的保护基团保护， A是低碳烷基等， X是一个脱离基团，且 m是0或1的整数， 在A为(C2-C6)碳烷基的情况下， m是1的整数， 当R1是式(A)的一个基团。
• Benzoxazepinones and their use as squalene synthase inhibitors
  申请人：——

  公开号：US20030078251A1

  公开（公告）日：2003-04-24

  There is disclosed a compound represented by the formula [I]: 1 wherein R 1 is optionally substituted 1-carboxyethyl group, optionally substituted alkyl-sulfonyl group, optionally substituted (carboxy-cycloalkyl)-alkyl group, —X 1 —X 2 —Ar—X 3 —X 4 —COOH (wherein X 1 and X 4 are a bond or alkylene group, X 2 and X 3 are a bond, —O—, —S—, Ar is divalent aromatic group etc.), R 2 is alkyl group optionally substituted with alkanoyloxy group and/or hydroxy group, R 3 is alkyl group, and W is halogen atom, etc., or a salt thereof. The compound has the cholesterol lowering activity and the triglyceride lowering activity and is useful for preventing and/or treating hyperlipidemia.

  披露了一种由公式[I]表示的化合物： 1 其中R 1 是可选地取代的1-羧乙基，可选地取代的烷基亚磺酰基，可选地取代的(羧基环烷基)-烷基，—X 1 —X 2 —Ar—X 3 —X 4 —COOH(其中X 1 和X 4 是键或亚烷基，X 2 和X 3 是键，—O—，—S—，Ar是二价芳香族等)，R 2 是可选地由酰氧基和/或羟基取代的烷基，R 3 是烷基，W是卤素原子等，或其盐。该化合物具有降低胆固醇活性和降低甘油三酯活性，用于预防或治疗高脂血症。
• o-Formylation of electron-rich phenols with dichloromethyl methyl ether and TiCl4
  作者：Oscar Garcı́a、Ernesto Nicolás、Fernando Albericio

  DOI：10.1016/s0040-4039(03)01168-7

  日期：2003.6

  o-Formylation of electron-rich phenols is accomplished with dichloromethyl methyl ether and TiCl4. The reaction gives excellent yields, good regioselectivity, and does not leading to diformylation.

  用二氯甲基甲基醚和TiCl 4可以完成富电子酚的邻甲酰化反应。该反应产生优异的产率，良好的区域选择性，并且不导致二甲酰化。
• [EN] CHROMENE DERIVATIVES AS ANTI-INFLAMMATORY AGENTS<br/>[FR] DERIVES DE CHROMENE A TITRE D'AGENTS ANTI-INFLAMMATOIRES
  申请人：PHARMACIA CORP

  公开号：WO2004087687A1

  公开（公告）日：2004-10-14

  The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula (I). Wherein Z, X, R1, R2, R3, and R4 are as described in the specification.

  该发明涉及在治疗与环氧合酶-2介导的疾病相关的情况中具有效用的方法和化合物。特别感兴趣的化合物是由式(I)定义的苯并吡喃和它们的类似物。其中Z、X、R1、R2、R3和R4如规范中所述。
• Orthoamide, LVII [1]. Lassen sich aromatische Aldehyde nach Fries aus Arylformiaten hersteilen? / Orthoamides, LVII [1]. Can Aromatic Aldehydes be Prepared from Aryl Formates via the Fries Rearrangement?
  作者：Georg Ziegler、Erwin Haug、Wolfgang Frey、Willi Kantlehner

  DOI：10.1515/znb-2001-1113

  日期：2001.11.1

  The aromatic hydroxyaldehydes 3a-3g, 5a-5f, 8 , 10 can be prepared by the action of BCl₃, BBr₃ or trifluoromethanesulfonic acid, on the aryl formates 1a-1f, 4a-e, 7, 9 via Fries rearrangement. BBr₃ is more effective than BCl₃. The activating ability of BBr₃ can be improved by addition of FeCl₃. Rearrangements which are induced by trifluoromethanesulfonic acid can give rise to the formations of regioisomers, which might be different from the products formed when the reaction is performed with Lewis acids. The yields of the aldehydes are lowered by subsequent condensation reactions. This view was confirmed by the isolation of a condensation product, which was characterized as a dibenzo[a,j]xanthene derivative 6 by crystal structure analysis. For the Fries rearrangement of formyl groups a new mechanism is proposed. 2-Hydroxy-1-naphthaldehyde 5c can be obtained in good yield from formic acid, BBr₃, and 2 -naphthol.

  芳香羟基醛类化合物3a-3g、5a-5f、8、10可通过BCl3、BBr3或三氟甲磺酸作用于芳基甲酸酯1a-1f、4a-e、7、9来制备，通过弗里斯重排反应。BBr3比BCl3更有效。BBr3的活化能力可以通过添加FeCl3来改善。由三氟甲磺酸诱导的重排反应可能导致产生位置异构体的形成，这与在Lewis酸存在下进行反应形成的产物可能不同。醛类产物的产率会因随后的缩合反应而降低。通过结晶结构分析，这一观点得到了验证，通过分离得到的缩合产物，被鉴定为二苯并[a，j]苯并二氢吖啶衍生物6。对于甲酰基团的弗里斯重排反应提出了一个新的机制。2-羟基-1-萘醛5c可以通过甲酸、BBr3和2-萘酚以较高的产率获得。