2,5-dimethoxy-3,6-dimethylbenzaldehyde | 104129-40-0

• 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: 2,5-dimethoxy-3,6-dimethylbenzaldehyde
• 英文别名: 2,5-dimethoxy-3,6-dimethyl-benzaldehyde；2,5-Dimethoxy-3,6-dimethyl-benzaldehyd
• CAS: 104129-40-0
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: MAHSGSRMRDCYSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dimethoxy-3,6-dimethylbenzaldehyde 在 sodium hydroxide 、 ammonium cerium(IV) nitrate 、 sodium methylate 、 四氯化钛 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 9.5h， 生成 (E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid
  参考文献：
  名称：

  Structure−Activity Relationships of (E)-3-(1,4-Benzoquinonyl)-2-[(3-pyridyl)- alkyl]-2-propenoic Acid Derivatives That Inhibit Both 5-Lipoxygenase and Thromboxane A₂ Synthetase

  摘要：

  As part of our research for the development of novel antiinflammatory drug candidates, we have designed and synthesized a series of (E)-3-(1,4-benzoquinonyl)-2-[(3-pyridyl)alkyl]-2-propenoic acid derivatives as dual inhibitors of 5-lipoxygenase (5-LO) and thromboxane (TX) A(2) synthetase. In order to increase the absorption after oral administration, we introduced a carboxylic acid moiety into the 1,4-benzoquinone skeleton, which has 5-LO-inhibitory character. Introduction of a 3-pyridylalkyl group at the double bond of the 1,4-benzoquinonyl propenoic acid moiety afforded good to moderate inhibitory activities against the production of leukotriene (LT) Bq and TXA(2) while not significantly inhibiting that of prostaglandin E(2) by glycogen-induced peritoneal cells of rat (in vitro). The length of the methylene chain of the 3-pyridylalkyl group influenced the inhibition of LTB(4) and TXB(2) production. An increase of lipophilicity by introducing a more lipophilic alkoxy group did not markedly increase the inhibitory activity on LTB(4) production. The position of an alkoxy group on the 1,4-benzoquinone skeleton played an important role in TXA(2) synthetase inhibition. Compounds such as 20c (E6700) with an appropriate alkoxy group and proper length of methylene side chain, together with a polar substituent (carboxylic acid), showed good inhibition of both 5-LO and TXA(2) synthetase and possess a variety of pharmacologically beneficial effects.

  DOI：

  10.1021/jm950725r
• 作为产物：
  描述：

  2,5-dimethylhydroquinone 在 盐酸 、 氢氧化钾 、 三氯化铝 、 苯 作用下， 生成 2,5-dimethoxy-3,6-dimethylbenzaldehyde
  参考文献：
  名称：

  THE CHEMISTRY OF VITAMIN E. XXVIII. (1) SYNTHESIS OF THE THREE DIMETHYLETHYLQUINONES

  摘要：

  DOI：

  10.1021/jo01203a008

文献信息

• Phenol derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05162571A1

  公开（公告）日：1992-11-10

  Novel phenol derivatives of the general formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X, Y and n are as defined in the specification, which have therapeutic and prophylactic activities against cerebral, cardiac, renal and pulmonary circulatory system diseases, respiratory diseases, allergy, anaphylactic shock, endotoxin shock, inflammation and the like as well as inhibiting activities against vascularization by oncocytes.

  具有以下一般式的新型酚衍生物：##STR1## 其中R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5、X、Y和n如规范中定义的那样，具有对大脑、心脏、肾脏和肺部循环系统疾病、呼吸系统疾病、过敏、过敏性休克、内毒素休克、炎症等的治疗和预防活性，以及对肿瘤细胞血管化的抑制活性。
• The directing effect of annelated rings in aromatic systems—II
  作者：J. Lars、G. Nilsson、H. Selander、H. Sievertsson、I. Skånberg

  DOI：10.1016/s0040-4020(01)97886-x

  日期：——

  2-dimethyl-5-benzofuranol gave a spiroketal trimer 10 by CC and CO coupling via the 6-position of the molecule. This indicates a directing effect on the oxidative coupling by the annelated 5-membered heterocyclic ring which is in accord with the predictions based on the Mills-Nixon effect. Similar oxidation of 2,3-dihydro-2,2,4,7-tetramethyl-5-benzofuranol and of 2,3-dihydro-2,2,6,7-tetramethyl-5-benzofuranol

  合成了与β-，γ-生育酚和母育酚有关的2,3二氢-5-苯并呋喃醇，并研究了其与碱性铁氰化物的氧化作用。2,3-二氢-2,2-二甲基-5-苯并呋喃醇的氧化通过分子的6位进行CC和CO偶合，得到了螺酮三聚体10。这表明退火的五元杂环对氧化偶联的指导作用，这与基于Mills-Nixon效应的预测相符。2,3-二氢-2,2,4,7-四甲基-5-苯并呋喃醇的相似氧化反应和2,3-二氢-2,2,6,7-四甲基-5-苯并呋喃醇的氧化反应（β-和γ的类似物-生育酚）分别通过涉及杂环开环的反应得到羟基醌11和12。
• Photoactivation of Amino-Substituted 1,4-Benzoquinones for Release of Carboxylate and Phenolate Leaving Groups Using Visible Light
  作者：Yugang Chen、Mark G. Steinmetz

  DOI：10.1021/jo060790g

  日期：2006.8.1

  a dark reaction. Lifetimes for elimination of 4-YC6H4OH in 30% phosphate buffer in CD3CN (pD 7) at 17 °C are 13.1, 0.54, and 0.13 h for Y = H, CF3, and CN, respectively, and the linear equation log k (h-1) = 0.998(−pKa) + 8.80 gives a best fit to the data. Carboxylate leaving groups are rapidly eliminated upon photolysis of the quinones in aq CH3CN to produce an o-quinone methide intermediate that is

  暴露于可见光后，2-吡咯烷基取代的3,6-二甲基-1,4-苯醌光环化生成苯并恶唑啉，其在CH 2 Cl 2中的量子产率为0.07-0.10 ，在CH 3 CN中的量子产率为0.02-0.04 ，且<0.01在30％CH 3 CN水溶液中。羧酸盐或苯酚盐的离去基团通过与醌的5-羟甲基偶合而结合，光环化作用得到苯并恶唑啉，这些苯并恶唑啉在黑暗反应中消除了离去基团。Y = H，CF 3和CN时，在17°C下消除CD 3 CN（pD 7）中30％磷酸盐缓冲液中的4-YC 6 H 4 OH的寿命分别为13.1，h，0.54和0.13h。线性方程log k（h- 1）= 0.998（-p ķ一）+ 8.80给出的最佳拟合到数据。在CH 3 CN中对醌进行光解后，羧酸酯离去基团会快速消除，从而生成邻醌甲基化物中间体，该中间体可通过4 + 2环加成与未反应的起始原料或添加的3-（二甲基氨基）-5,5-二甲
• Photochemical Cyclization with Release of Carboxylic Acids and Phenol from Pyrrolidino-Substituted 1,4-Benzoquinones Using Visible Light
  作者：Yugang Chen、Mark G. Steinmetz

  DOI：10.1021/ol051362k

  日期：2005.8.1

  rolidino-1,4-benzoquinones effects photoisomerization to labile oxazolidines, which undergo elimination of carboxylate or phenolate leaving groups in high yields to generate trappable o-quinone methide intermediates. [reaction: see text]

  5-酰氧基甲基-和5-苯氧基甲基-2-吡咯烷基-1,4-苯醌的可见光照射使光致异构化为不稳定的恶唑烷，恶唑烷以高收率消除羧酸盐或酚盐残基，从而生成可捕集的邻醌甲基化物中间体。[反应：看文字]
• Tricyclic dihydrobenzofuran derivatives, process for the preparation thereof and agents
  申请人：Ohkawa Shigenori

  公开号：US06872718B1

  公开（公告）日：2005-03-29

  A compound represented by the formula: wherein Ring A is a non-aromatic 5- to 7-membered nitrogen-containing heterocyclic ring which may be further substituted, Ring B is benzene ring which is further substituted, Ring C is a dihydrofuran-ring which may be further substituted and R is hydrogen atom or an acyl group or a salt thereof has an excellent lipid peroxidation inhibitory activity and is useful as a lipid peroxidation inhibitor.

  一种化合物的化学式表示为：其中环A是一种非芳香性的5-至7元素含氮杂环，其可能进一步被取代，环B是苯环，其进一步被取代，环C是二氢呋喃环，其可能进一步被取代，R是氢原子或酰基或其盐。该化合物具有出色的脂质过氧化抑制活性，并可用作脂质过氧化抑制剂。