3,4,5-Trimethoxybenzaldehyde diethyl acetal | 101403-71-8

• 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: 3,4,5-Trimethoxybenzaldehyde diethyl acetal
• 英文别名: 5-(diethoxymethyl)-1,2,3-trimethoxybenzene
• CAS: 101403-71-8
• 化学式: C₁₄H₂₂O₅
• 分子量: 270.326
• InChiKey: LJVMMSLDHJFUEX-UHFFFAOYSA-N

物化性质

• 沸点：
  325.7±42.0 °C(Predicted)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4,5-Trimethoxybenzaldehyde diethyl acetal 在 sodium 、 溶剂黄146 作用下， 反应 33.0h， 生成 3,5-二甲氧基苯甲醛
  参考文献：
  名称：

  Regioselective reductive electrophilic substitution of derivatives of 3,4,5-trimethoxybenzaldehyde

  摘要：

  The behavior of several protected derivatives of 3,4,5-trimethoxybenzaldehyde has been investigated under conditions of electron transfer from alkali metals in aprotic solvents. The 4-methoxy group can be regioselectively removed in good to high yield under such conditions, and an appropriate choice of the protecting group, metal, and solvent allows its substitution with a variety of electrophiles. 3,4,5-Trimethoxybenzaldehyde dimethyl acetal, 1, is the starting material of choice for a new general synthetic approach to several polysubstituted resorcinol dimethyl ethers. Investigation of the mechanism of demethoxylation, with the aid of labeling experiments, showed that reductive demethoxylation is strongly influenced by the nature of the aldehyde protective group employed.

  DOI：

  10.1021/jo00037a029
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 原甲酸三乙酯 在 tropylium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以89%的产率得到3,4,5-Trimethoxybenzaldehyde diethyl acetal
  参考文献：
  名称：

  Tropylium盐是有效的有机路易斯酸催化剂，可分批和连续地进行缩醛化和反缩醛化反应

  摘要：

  羰基化反应在羰基化合物重要的掩蔽化学中起着重要的作用。在本文中，我们首次证明了对钾盐可以用作有机路易斯酸催化剂，以促进各种醛底物的缩醛化和反缩醛化反应。这种无金属方法在间歇和流动条件下均能有效工作，从而促进了对硝基有机催化剂在绿色合成中的进一步应用。

  DOI：

  10.1039/c7gc01519d

文献信息

• Cobalt(II)-catalyzed chemoselective synthesis of acetals from aldehydes
  作者：Subbarayan Velusamy、T Punniyamurthy

  DOI：10.1016/j.tetlet.2004.04.126

  日期：2004.6

  The acetalization of aldehydes has been studied with methanol, ethanol, and 2-propanol using CoCl2 in high yields under reflux conditions. The reaction is simple, efficient, chemoselective and does not involve any other additive.

  已经在回流条件下以高收率研究了使用CoCl 2的甲醇，乙醇和2-丙醇对醛的缩醛化作用。该反应简单，有效，化学选择性并且不涉及任何其他添加剂。
• Synthesis and antitumor activity of tropolone derivatives. 3
  作者：Masatoshi Yamato、Kuniko Hashigaki、Nobuhiko Kokubu、Tazuko Tashiro、Takashi Tsuruo

  DOI：10.1021/jm00157a014

  日期：1986.7

  As part of a study on the antitumor activities of tropolone derivatives prepared from hinokitiol, which naturally occurs in the plants of Chamaecyparis species, effects of aromatic substituents of alpha,alpha-bis(7-hydroxy-5-isopropyltropon-2-yl)toluenes on the activity were examined. Several of the compounds showed high potency in the P388 leukemia assay. 4-Hydroxy analogue 4d showed the most potent

  作为研究由扁柏酚类化合物制得的托酚酮衍生物的抗肿瘤活性的一部分，香酚醇是天然存在于Chamaecyparis物种的植物中的，α，α-双（7-羟基-5-异丙基肌醇-2-基）甲苯的芳族取代基的作用对活动进行了检查。几种化合物在P388白血病检测中显示出高效力。4-羟基类似物4d在5 mg / kg剂量下显示出最有效的活性（T / C = 195％）。引入大的取代基，其空间影响阻止了取代的芳族官能团的共面性，导致效力显着降低。进行了高效4-甲氧基类似物4b的X射线结构分析。
• Process for producing maltooligosaccharide derivative
  申请人：WAKO PURE CHEMICAL INDUSTRIES LTD

  公开号：EP0566366A2

  公开（公告）日：1993-10-20

  A polyacyl maltooligosaccharide derivative which is a precursor of a maltooligosaccharide derivative having modified groups at the 6-position or 4- and 6-positions of non-reducing end glucose unit and being effectively used as a substrate for measuring a-amylase activity, can be produced under mild conditions by crosslinking OH groups in the non-reducing end glucose unit of oligosaccharide with a benzylidene group having an alkoxy group, followed by acylation and treatment with a dilute acid.

  一种多酰基麦芽寡糖衍生物是在非还原端葡萄糖单元的 6 位或 4 位和 6 位上具有修饰基团的麦芽寡糖衍生物的前体，可有效地用作测定 a-淀粉酶活性的底物，这种衍生物可在温和的条件下通过将寡糖非还原端葡萄糖单元中的 OH 基团与具有烷氧基的亚苄基交联，然后进行酰化并用稀酸处理而制得。
• A solvent-controlled highly efficient Pd–C catalyzed hydrogenolysis of benzaldehydes to methylbenzenes via a novel ‘acetal pathway’
  作者：Lixin Xing、Xinyan Wang、Chuanjie Cheng、Rui Zhu、Bo Liu、Yuefei Hu

  DOI：10.1016/j.tet.2007.06.105

  日期：2007.9

  Pd-C catalyzed hydrogenolysis of benzaldehydes to methylbenzenes has been described to proceed via a 'benzenemethanol pathway'. In this article, a novel 'acetal pathway' was first revealed by a systematic study when lower alcohols were used as solvents and a solvent-controlled highly efficient procedure was established. (C) 2007 Elsevier Ltd. All rights reserved.
• US5393876A
  申请人：——

  公开号：US5393876A

  公开（公告）日：1995-02-28