2-(2,6-dimethoxyphenoxy)acetaldehyde | 71084-47-4

• 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-(2,6-dimethoxyphenoxy)acetaldehyde
• 英文别名: (2,6-dimethoxyphenoxy)acetaldehyde；2,6-dimethoxyphenoxy-acetaldehyde
• CAS: 71084-47-4
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: UOBSJOUJKBGJMU-UHFFFAOYSA-N

物化性质

• 沸点：
  284.9±25.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,6-dimethoxyphenoxy)acetaldehyde 在 盐酸 、 4 A molecular sieve 、 sodium cyanoborohydride 、 potassium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 反应 152.25h， 生成 N-benzyl-N-(2-chloroethyl)-N-[2-(2,6-dimethoxyphenoxy)ethyl]amine hydrochloride
  参考文献：
  名称：

  Structure–Activity relationships among novel phenoxybenzamine-Related β-Chloroethylamines

  摘要：

  A series of beta-chloroethylamines 5-18, structurally related to the irreversible alpha(1)-adrenoceptor antagonist phenoxy-benzamine [PB, N-benzyl-N-(2-chloroethyl)-N-(1-methyl-2-phenoxyethyl)amine hydrochloride, 1] and the competitive antagonist WB4101 [N-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-N-[2-(2,6-dimethoxyphenoxy)ethyl]amine hydrochloride, 2], were synthesized and evaluated for their activity at alpha-adrenoceptors of the epididymal and the prostatic portion of young CD rat vas deferens. All compounds displayed irreversible antagonist activity. Most of them showed similar antagonism at both alpha(1)- and alpha(2)-adrenoceptors, whereas compounds 13 and 18, lacking substituents on both the phenoxy group and the oxyamino carbon chain, displayed a moderate alpha(1)-adrenoceptor selectivity (10-35 times), which was comparable to that of PB. Compounds 14 and 15, belonging to the benzyl series and bearing, respectively, a 2-ethoxyphenoxy and a 2-i-propoxyphenoxy moiety, were the most potent alpha(1)-adrenoceptor antagonists with an affinity value similar to that Of PB (pIC(50) values of 7.17 and 7.06 versus 7.27). Interestingly, several compounds were able to distinguish two alpha(1)-adrenoceptor subtypes in the epididymal tissue, as revealed by the discontinuity of their inhibition curves. A mean ratio of 24:76 for these alpha(1)-adrenoceptors was determined from compounds 8-10, 12, and 15-17. Furthermore, compounds 9, 10, 12, 16a, and 16b showed higher affinity towards the minor population of receptors, whereas compounds 8, 15, and 17 preferentially inhibited the major population of alpha(1)-adrenoceptors. In addition, selected pharmacological experiments demonstrated the complementary antagonism of the two series of compounds and their different, preferential affinity for one of the two alpha(1)-adrenoceptor subtypes. In conclusion, we found beta-chloroethylamines that demonstrate a multiplicity of alpha(1)-adrenoceptors in the epididymal portion of young CD rat vas deferens and, as a consequence, they are possible useful tools for alpha(1)-adrenoceptor characterization. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00395-9
• 作为产物：
  描述：

  2,6-二甲氧基苯酚 在 盐酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 2-(2,6-dimethoxyphenoxy)acetaldehyde
  参考文献：
  名称：

  甘油衍生物的绝对构型。7.2-[[[[2-（2，6-二甲氧基苯氧基）乙基]氨基]甲基] -1，4-苯并二恶烷（WB-4101）的对映异构体（WB-4101），一种有效的竞争性α-肾上腺素拮抗剂。

  摘要：

  由手性2-[[（甲苯磺酰氧基）甲基] -1,4-制备2-[[[[[2-（2,6-二甲氧基苯氧基）乙基]氨基]甲基] -1,4-苯并二恶烷（4）的对映异构体。苯并二恶烷[（2S）-和（2R）-5]。相应的（2R）-和（2S）-2-（氨基乙基）-1,4-苯并二恶烷[2R）-和（2S）-7]是通过修饰的加百利合成法制备的，并通过与2,6-二甲氧基苯氧基乙醛（8）并用NaBH4还原中间体亚胺。对映体（2S）-4在对抗甲氧胺引起的兔主动脉条收缩的α-肾上腺素能反应中的效力是对映体（2R）-4的40--50倍，显示pA2 = 9.0。该结果与先前的观察结果一致，即2-[（（烷基氨基）甲基]苯并二恶烷的S对映异构体在α-肾上腺素受体上比R对映异构体更有效。

  DOI：

  10.1021/jm00195a024

文献信息

• Singlet oxygen in the photodegradation of lignin models
  作者：Claudia Crestini、Maurizio D'Auria

  DOI：10.1016/s0040-4020(97)00460-2

  日期：1997.6

  of the carbonyl group is not indispensable to have the cleavage reaction. The use of the model compound 10 showed that, when the phenoxy part of the molecule shows a lower reactivity towards singlet oxygen, the oxidation of the phenol moiety to hydroquinone can occur. The photochemical behaviour of these model compounds can be rationalised from a reaction of singlet oxygen with the phenoxy part of the

  研究了单线态氧存在下木质素模型的光化学氧化。所述非酚β-O-4芳基醚衍生物的治疗6，7和8在氧和玫瑰红的存在，得到的产品从一个正式的β-CO裂解形成导出。通过这种方式，衍生物12，13，和15获得的。酚类β-O-4芳基酯9的光化学氧化得到相同类型的产物，证实在这种情况下，羰基的存在对于裂解反应不是必不可少的。模型化合物10的使用结果表明，当分子的苯氧基部分显示出对单线态氧较低的反应性时，酚部分会氧化为对苯二酚。这些模型化合物的光化学行为可以通过单线态氧与分子的苯氧基部分的反应来合理化。
• Organocatalytic Chemoselective Primary Alcohol Oxidation and Subsequent Cleavage of Lignin Model Compounds and Lignin
  作者：Saumya Dabral、José G. Hernández、Paul C. J. Kamer、Carsten Bolm

  DOI：10.1002/cssc.201700703

  日期：2017.7.10

  A one-pot two-step degradation of lignin β-O-4 model compounds initiated by preferred oxidation of the primary over the secondary hydroxyl groups with a TEMPO/DAIB system has been developed [TEMPO=2,2,6,6-tetramethylpiperidine-N-oxyl, DAIB=(diacetoxy)iodobenzene]. The oxidised products are then cleaved by proline-catalysed retro-aldol reactions. This degradation methodology produces simple aromatics

  已开发出通过使用TEMPO / DAIB系统将伯优先于仲羟基进行优选氧化而引发的木质素β-O-4模型化合物的一锅两步降解[TEMPO = 2,2,6,6-四甲基哌啶- ñ -1-氧基，DAIB =（二乙酰氧基）碘代苯]。然后，氧化产物通过脯氨酸催化的逆醛醇缩合反应裂解。该降解方法在室温下以木质素模型化合物的高收率生产出简单的芳族化合物，并扩展至有机溶剂山毛榉木木质素（L1），从而产生已知的裂解产物。
• Bicyclic heterocyclic derivatives having .alpha..sub.1 adrenergic and
  申请人：Recordati S.A., Chemical and Pharmaceutical Company

  公开号：US05605896A1

  公开（公告）日：1997-02-25

  This invention provides bicyclic heterocyclic derivatives and their pharmaceutically acceptable salts useful for the treatment of hypertension, urethral and lower urinary tract contractions, and other disorders. The compounds are also useful for binding .alpha..sub.1 -adrenergic and 5HT.sub.1A serotonergic receptors, in vitro or in vivo.

  本发明提供了双环杂环衍生物及其药学上可接受的盐，用于治疗高血压、尿道和下泌尿道收缩以及其他疾病。这些化合物还可用于体外或体内结合.alpha..sub.1-肾上腺素能和5HT.sub.1A-5-羟色胺能受体。
• Bicyclic heterocyclic derivatives having .alpha..sub.1 -adrenergic and
  申请人：Recordati S.A., Chemical and Pharmaceutical Company

  公开号：US05474994A1

  公开（公告）日：1995-12-12

  This invention provides bicyclic heterocyclic derivatives and their pharmaceutically acceptable salts useful for the treatment of hypertension, urethral and lower urinary tract contractions, and other disorders. The compounds are also useful for binding .alpha..sub.1 -adrenergic and 5HT.sub.1A serotonergic receptors, in vitro or in vivo.

  本发明提供了双环杂环衍生物及其药学上可接受的盐，用于治疗高血压、尿道和下泌尿道收缩以及其他疾病。该化合物还可用于体外或体内结合α1-肾上腺素能和5HT1A-5-羟色胺能受体。
• 4-Aralkyl-1,4-dihydropyridine, Verfahren zu deren Herstellung, ihre Verwendung in Arzneimitteln sowie deren Herstellung
  申请人：BAYER AG

  公开号：EP0042093A2

  公开（公告）日：1981-12-23

  Die Erfindung betrifft neue 4-Aralkyl-1,4-dihydropyridine, mehrere Verfahren zu ihrer Herstellung, ihre Verwendung als Arzneimittel, insbesondere zur Beeinflussung von Kreislauferkrankungen, diese enthaltende Arzneimittel, sowie deren Herstellung.

  本发明涉及新的 4-烷基-1,4-二氢吡啶、其制备的几种工艺、其作为药物（尤其是用于影响循环系统疾病）的用途、含有它们的药物及其制备方法。