4-(二乙氧基甲基)苯甲腈 | 66739-88-6

• 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: 4-(二乙氧基甲基)苯甲腈
• 英文名称: 4-cyanobenzaldehyde diethyl acetal
• 英文别名: p-Cyanobenzaldehyde diethylacetal；4-(diethoxymethyl)benzonitrile；4-diethoxymethylbenzonitrile；4-Cyanobenzaldehyddiethylacetal
• CAS: 66739-88-6
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: BVMFTWLHDCSXDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(二乙氧基甲基)苯甲腈 在 palladium diacetate 、 potassium fluoride 、 硼酸三异丙酯 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 2-(二环己基膦基)联苯 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 4-formyl-2-(8-quinolinyl)benzonitrile
  参考文献：
  名称：

  Enantioselective synthesis of the farnesyltransferase inhibitor, A-345665.0

  摘要：

  The stereoselective synthesis of A-345665.0 1, a novel farnesyl transferase inhibitor, is described. The key step involves a stereoselective addition of an imidazolyl Grignard reagent to aldehyde 8 in the presence of an external chiral auxiliary. Crystallization of the product as the dimeric zinc complex 12 facilitates the isolation of product in > 98:2 er. The biaryl linkage is formed by the use of a Suzuki coupling, employing boronic acid 4 prepared by the directed ortho-lithiation of benzonitrile 6. The overall yield for the six step sequence is 21%. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.008
• 作为产物：
  描述：

  4-Diethoxymethyl-benzaldehyde oxime 在 nickel(II) chloride hexahydrate 作用下， 以 乙腈 为溶剂， 以57%的产率得到4-(二乙氧基甲基)苯甲腈
  参考文献：
  名称：

  Ligand-Free Nickel-Catalyzed Conversion of Aldoximes into Nitriles

  摘要：

  在中性温和的条件下，在乙腈中使用 NiCl2 可以高效地催化醛肟脱水。在这些条件下，各种官能化醛肟都能以良好到极佳的收率生成相应的腈。

  DOI：

  10.1055/s-0030-1260119

文献信息

• Direct anodic (thio)acetalization of aldehydes with alcohols (thiols) under neutral conditions, and computational insight into the electrochemical formation of the acetals
  作者：Caiyan Liu、Yongli Shen、Zihui Xiao、Hui Yang、Xue Han、Kedong Yuan、Yi Ding

  DOI：10.1039/c9gc01554j

  日期：——

  A versatile protocol for the production of acetals/thioacetals by means of direct electrochemical oxidation is developed here under neutral conditions, providing (thio)acetals with good functional group tolerance and a wide scope for both aldehydes and (thio)alcohols. DFT calculations reveal that direct electron transfer from the anode plays a key role in carbonyl activation during this acid free acetalization

  在中性条件下，开发了一种通过直接电化学氧化生产乙缩醛/硫缩醛的通用协议，为（硫代）乙缩醛提供了良好的官能团耐受性，并且对于醛和（硫代）醇都具有广泛的适用范围。DFT计算表明，在这种无酸的缩醛化过程中，来自阳极的直接电子转移在羰基活化中起关键作用。
• A Mild TEMPO-Catalyzed Aerobic Oxidative Conversion of Aldehydes into Nitriles
  作者：Chaojie Fang、Meichao Li、Xinquan Hu、Weimin Mo、Baoxiang Hu、Nan Sun、Liqun Jin、Zhenlu Shen

  DOI：10.1002/adsc.201501130

  日期：2016.3.31

  to prepare nitriles from aldehydes using hexamethyldisilazane (HMDS) as the nitrogen source has been developed. The reactions were performed with 2,2,6,6‐tetramethylpiperidine l‐oxyl (TEMPO) as the catalyst, NaNO2 or TBN as the co‐catalyst, and molecular oxygen as the terminal oxidant under mild conditions. A variety of aromatic, heteroaromatic, aliphatic and allylic aldehydes could be converted into

  已经开发出一种以六甲基二硅氮烷（HMDS）为氮源，由醛制备腈的有效方法。反应在温和条件下以2,2,6,6-四甲基哌啶-1-氧基（TEMPO）为催化剂，NaNO 2或TBN为助催化剂，分子氧为末端氧化剂。各种芳族，杂芳族，脂族和烯丙基醛都可以良好或优异的产率转化为相应的腈。
• A practical iodine-catalyzed oxidative conversion of aldehydes to nitriles
  作者：Chaojie Fang、Meichao Li、Xinquan Hu、Weimin Mo、Baoxiang Hu、Nan Sun、Liqun Jin、Zhenlu Shen

  DOI：10.1039/c6ra26435b

  日期：——

  A simple and efficient method for the direct synthesis of nitriles from aldehydes using ammonium acetate as the nitrogen source has been developed. The reactions were performed with iodine as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant under mild conditions. A variety of aromatic, heteroaromatic, aliphatic and allylic aldehydes could be converted into their corresponding nitriles

  已经开发出一种简单有效的方法，可以使用乙酸铵作为氮源，从醛类直接合成腈。反应在温和条件下以碘为催化剂，以叔丁基氢过氧化物（TBHP）为氧化剂进行。各种芳族，杂芳族，脂族和烯丙基醛都可以良好或优异的产率转化为相应的腈。
• α-Chymotrypsin-Induced Acetalization of Aldehydes and Ketones with Alcohols
  作者：Zhanggao Le、Zongbo Xie、Jin Lan、Guofang Jiang、Jiangnan Yang、Haibo Zhu

  DOI：10.1055/s-0039-1690883

  日期：2020.7

  This is the first report of a simple and general method for acetalization­ of aldehydes via an α-chymotrypsin-induced reaction under mild conditions. A broad range of aromatic and heteroaromatic aldehydes have been acetalized under neutral conditions in good yields using a catalytic amount of chymotrypsin.

  这是在温和条件下通过α-胰凝乳蛋白酶诱导的反应进行乙醛缩醛化的简单通用方法的首次报道。在中性条件下，使用催化量的胰凝乳蛋白酶以高收率将各种芳香族和杂芳香族醛缩醛化。
• Visible-Light-Induced Acetalization of Aldehydes with Alcohols
  作者：Hong Yi、Linbin Niu、Shengchun Wang、Tianyi Liu、Atul K. Singh、Aiwen Lei

  DOI：10.1021/acs.orglett.6b03403

  日期：2017.1.6

  have achieved a simple and general method for acetalization of aldehydes by means of a photochemical reaction under low-energy visible light irradiation. A broad range of aromatic, heteroaromatic, and aliphatic aldehydes have been protected under neutral conditions in good to excellent yields using a catalytic amount of Eosin Y as the photocatalyst. Our visible light mediated acetalization strategies are

  在这项工作中，我们通过在低能可见光照射下进行光化学反应，实现了一种简单而通用的醛缩醛化方法。使用催化量的曙红Y作为光催化剂，在中性条件下以良好或优异的收率保护了多种芳香族，杂芳香族和脂肪族醛。我们的可见光介导的缩醛化策略可成功用于更具挑战性的酸敏感性醛和位阻醛。值得注意的是，该方案对醛具有化学选择性，而酮则保持完整。