3,5-二甲氧基苯甲醛二甲基缩醛 | 59276-34-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,5-二甲氧基苯甲醛二甲基缩醛
• 中文别名: 尼达尼布杂质69
• 英文名称: 3,5-dimethoxybenzaldehyde dimethyl acetal
• 英文别名: 1,3-Dimethoxy-5-(dimethoxymethyl)benzene；1-(dimethoxymethyl)-3,5-dimethoxybenzene
• CAS: 59276-34-5
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: PYLOSNCLXOMVDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二甲氧基苯甲醛二甲基缩醛 在 溶剂黄146 作用下， 反应 5.0h， 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二甲基缩醛 在 sodium 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 3,5-二甲氧基苯甲醛二甲基缩醛
  参考文献：
  名称：

  Ion pairing effects on the regioselectivity of arylic versus benzylic C–O bond reductive cleavage: synthetic applications

  摘要：

  The regioselectivity of the reductive cleavage of 3,4,5-trimethoxybenzyl methyl ether strongly depends on the alkali metal employed as a reducing agent and solvent effects. Reactions run using Na as a reducing agent led to aromatic C(4)-O bond cleavage, whilst reductions run in the presence of Na/15-crown-5, or using Li as a reducing agent, led to highly regioselective benzylic C-O bond cleavage. This regioselectivity turnaround is discussed in terms of major solvent effects affecting the fragmentation paths of a common reaction intermediate. Synthetic applications of these findings led to the synthesis of biologically active compounds, like 2,5-dialkyl-substituted resorcinols, or 1-(3,4,5-trimethoxyphenyl)-2-arylethanes structurally related to combretastatin. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.010

文献信息

• The use of electroosmotic flow as a pumping mechanism for semi-preparative scale continuous flow synthesis
  作者：Charlotte Wiles、Paul Watts、Stephen J. Haswell

  DOI：10.1039/b614559k

  日期：——

  By employing a series of reactions we demonstrate the use of electroosmotic flow as a continuous pumping mechanism suitable for semi-preparative scale synthesis, affording an array of small organic compounds, of analytical purity, with yields ranging from 0.57–1.71 g h−1.

  通过采用一系列反应，我们证明了将电渗流作为一种连续泵送机制应用于半制备规模的合成，能够获得一系列小有机化合物，其分析纯度下的产率范围为每小时0.57至1.71克。
• Structurally Simple Benzylidene-Type Photolabile Diol Protecting Groups
  作者：Xiong Ding、Dattatray A. Devalankar、Pengfei Wang

  DOI：10.1021/acs.orglett.6b02777

  日期：2016.10.21

  Two structurally simple photolabile protecting groups for releasing 1,2- and 1,3-diols have been developed. The diols can be protected in high yields and released from their corresponding acetals with high chemical efficiency.

  已经开发了两种结构简单的对光不稳定的用于释放1,2-和1,3-二醇的保护基。可以以高收率保护二醇，并以高化学效率将其从其相应的缩醛中释放出来。
• Synthesis and Complement Inhibitory Activity of B/C/D-Ring Analogues of the Fungal Metabolite 6,7-Diformyl-3‘,4‘,4a‘,5‘,6‘,7‘,8‘,8a‘-octahydro-4,6‘,7‘-trihydroxy- 2‘,5‘,5‘,8a‘-tetramethylspiro[1‘(2‘<i>H</i>)-naphthalene-2(3<i>H</i>)-benzofuran]
  作者：Barton J. Bradbury、Piotr Bartyzel、Teodoro S. Kaufman、Marcelo J. Nieto、Robert D. Sindelar、Susanne M. Scesney、Bruce R. Gaumond、Henry C. Marsh

  DOI：10.1021/jm0204284

  日期：2003.6.1

  )-cyclohexane] partial analogues (5) of the complement inhibitory sesquiterpene fungal metabolite 6,7-diformyl-3',4',4a',5',6',7',8',8a'-octahydro-4,6',7'-trihydroxy-2',5',5',8a'- tetramethylspiro[1'(2'H)-naphthalene-2(3H)-benzofuran] (1a, K-76) and its silver oxide oxidized product (1b, K-76COOH). The described target compounds represent spirobenzofuran B/C/D-ring analogues lacking the A-ring component

  本文报道了补体抑制倍半萜真菌代谢产物6,7-二甲酰基-3'，4'的4-甲氧基和4-羟基螺[苯并呋喃-2（3H）-环己烷]部分类似物（5）的合成和生物测定。 ，4a'，5'，6'，7'，8'，8a'-八氢-4,6'，7'-三羟基-2'，5'，5'，8a'-四甲基螺[1'（2' H）-萘-2（3H）-苯并呋喃]（1a，K-76）及其氧化银氧化产物（1b，K-76COOH）。所述目标化合物代表缺少原型结构的A环成分的螺苯并呋喃B / C / D环类似物。通过抑制人血清中的总溶血补体活性来评估目标化合物。观察到结构简化的类似物4-甲氧基螺[苯并呋喃-2（3H）-环己烷] -6-羧酸（5a）的IC（50）= 0。53 mM类似于对天然产物衍生物1b观察到的IC（50）= 0.57 mM。发现IC（50）= 0.16 mM，三环部分结构6-羧基-7-甲酰基-4-甲氧基螺[苯并呋喃-2（3H）-环己烷]
• Protected <i>syn</i>-Aldol Compounds from Direct, Catalytic, and Enantioselective Reactions of <i>N</i>-Acyl-1,3-oxazinane-2-thiones with Aromatic Acetals
  作者：Miguel Mellado-Hidalgo、Elias A. Romero-Cavagnaro、Sajanthanaa Nageswaran、Sabrina Puddu、Stuart C. D. Kennington、Anna M. Costa、Pedro Romea、Fèlix Urpí、Gabriel Aullón、Mercè Font-Bardia

  DOI：10.1021/acs.orglett.2c04254

  日期：2023.2.3

  A direct and asymmetric syn-aldol reaction of N-acyl-1,3-oxazinane-2-thiones with dialkyl acetals from aromatic acetals in the presence of 2–5 mol % [DTBM-SEGPHOS]NiCl2, TMSOTf, and lutidine has been developed. It has been established that the oxazinanethione heterocycle, used for the first time as a scaffold in asymmetric carbon–carbon bond-forming reactions, can be smoothly removed to give access

  在 2–5 mol % [DTBM-SEGPHOS]NiCl 2、TMSOTf 和二甲基吡啶存在下， N -acyl-1,3-oxazinane-2-thiones 与来自芳香族缩醛的二烷基缩醛的直接和不对称顺式-aldol反应具有被开发。已经确定，首次用作不对称碳-碳键形成反应支架的恶嗪硫酮杂环可以顺利去除，从而获得各种具有高合成价值的对映体纯化合物。
• Acid-catalysed synthesis and deprotection of dimethyl acetals in a miniaturised electroosmotic flow reactor
  作者：Charlotte Wiles、Paul Watts、Stephen J. Haswell

  DOI：10.1016/j.tet.2005.03.082

  日期：2005.5

  Through incorporating a series of polymer-supported acid catalysts into a miniaturised EOF-based flow reactor, we demonstrate a clean and efficient technique for the protection of aldehydes as their respective dimethyl acetal. In addition, we also report the acid catalysed deacetalisation of 11 dimethyl acetals to their respective aldehyde. In all cases, the compounds described are obtained in high yield (> 95%) and excellent purity (> 99%) without the need for further product purification. (c) 2005 Elsevier Ltd. All rights reserved.