2-氯苯甲醛二乙缩醛 | 35364-86-4

• 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: 2-氯苯甲醛二乙缩醛
• 英文名称: 2-chlorobenzaldehyde diethyl acetal
• 英文别名: 1-chloro-2-(diethoxymethyl)benzene；benzene, 1-chloro-2-diethoxymethyl-；o-Cl-Benzaldehyd-diaethylacetal；o-chlorobenzaldehyde diethyl acetal
• CAS: 35364-86-4
• 化学式: C₁₁H₁₅ClO₂
• 分子量: 214.692
• InChiKey: BVAOFFFFYDZUNU-UHFFFAOYSA-N

物化性质

• 沸点：
  123-124 °C(Press: 15 Torr)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯苯甲醛二乙缩醛 以83%的产率得到2-甲酰基苯硼酸
  参考文献：
  名称：

  Method for producing formylphenylboronic acids

  摘要：

  通过在惰性溶剂中用锂与保护氯苯甲醛（II）反应，形成公式（III）化合物，然后与公式BY3的硼化合物进行反应，制备公式（I）的甲酰苯基硼酸的制备方法。

  公开号：

  US20040049050A1
• 作为产物：
  描述：

  乙醇 、 2-氯苯甲醛 在 poly(ethylene glycol) 1000 based dicationic acidic ionic liquid 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以90%的产率得到2-氯苯甲醛二乙缩醛
  参考文献：
  名称：

  A facile and efficient protocol for esterification and acetalization in a PEG1000-D(A)IL/toluene thermoregulated catalyst–media combined systems

  摘要：

  A novel efficient and recyclable temperature-dependent biphasic catalyst and reaction media combined system comprised of PEG-1000 linked dicationic acidic ionic liquid and toluene was developed and applied in esterification of aromatic acids and acetalization of aromatic aldehydes with good to excellent yields. This system is characteristic of temperature-dependent reversible biphasic property, simple and facile recyclability, high catalytic activity and extensive substrate and reaction adaptability. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2013.07.013

文献信息

• 2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO), N-Bromosuccinimide (NBS) and Bromine as Efficient Catalysts for Dithioacetalization and Oxathioacetalization of Carbonyl Compounds and Transdithioacetalization Reactions
  作者：Nasser Iranpoor、Habib Firouzabadi、Hamid Reza Shaterian、M. A. Zolfigol

  DOI：10.1080/10426500211712

  日期：2002.5.1

  6-tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS), and bromine as efficient catalysts for conversion of carbonyl compounds to their cyclic and acyclic dithioacetals and 1,3-oxathiolanes under mild reaction conditions are described. These catalysts are also used for efficient transdithioacetalization of acetals, diacetals, ketals, acylals, enamines, hydrazones, and oximes with high

  使用 2,4,4,6-四溴-2,5-环己二烯酮 (TABCO)、N-溴代琥珀酰亚胺 (NBS) 和溴作为有效催化剂将羰基化合物转化为环状和无环二硫缩醛和 1,3-描述了在温和反应条件下的硫杂环戊烷。这些催化剂还用于在硫醇存在下以高产率有效地将缩醛、二缩醛、缩酮、酰基、烯胺、腙和肟转二硫缩醛。
• A convenient and practical method for the synthesis ofN-thiophosphoryl aldimines and ketimines
  作者：Xinyuan Xu、Chungui Wang、Zhenghong Zhou、Zebing Zeng、Xinpeng Ma、Guofeng Zhao、Chuchi Tang

  DOI：10.1002/hc.20412

  日期：2008.4

  A convenient and practical method for the preparation of N-thiophosphoryl imines was developed through the thermal condensation of acetals with different thiophosphoramides at 120–160°C. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:238–244, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20412

  通过缩醛与不同硫代磷酰胺在 120-160°C 下的热缩合，开发了一种方便实用的制备 N-硫代磷酰亚胺的方法。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:238–244, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20412
• Nucleophilic phosphine-catalyzed [3+2] cycloaddition of allenes with N-(thio)phosphoryl imines and acidic methanolysis of adducts N-(thio)phosphoryl 3-pyrrolines: a facile synthesis of free amine 3-pyrrolines
  作者：Bo Zhang、Zhengrong He、Silong Xu、Guiping Wu、Zhengjie He

  DOI：10.1016/j.tet.2008.07.075

  日期：2008.9

  In this report, the dipolarophile imines with easily removable activating group O,O-diethyl(thio)phosphoryl have been investigated in the nucleophilic phosphine-catalyzed [3+2] cycloaddition reaction of electron-deficient allenes. Under the catalysis of a tertiary phosphine, N-(thio)phosphorylimines readily undergo the [3+2] cycloaddition reaction with ethyl 2,3-butadienoate or ethyl 2,3-pentadienoate

  在该报告中，已经在亲电子膦催化的缺电子异戊烯的[3 + 2]环加成反应中研究了具有易于除去的活化基团O，O-二乙基（硫代）磷酰基的偶极亲子亚胺。在叔膦的催化下，N-（硫代）磷酸亚胺与2,3-丁二烯酸乙酯或2,3-戊二烯酸乙酯容易进行[3 + 2]环加成反应，得到相应的N-（硫代）磷酰基3-吡咯啉，中等至高收率，具有良好的非对映选择性。已通过PN键的酸性甲醇分解成功地从加合物中去除了（硫代）磷酰基，从而使游离胺3-吡咯啉的收率达到了中等至良好的收率，而没有发生严重的芳构化。因此，由膦与亚胺的膦催化的[3 + 2]环加成反应建立了N-未取代的3-吡咯啉的简便合成方法。
• Practical acetalization and transacetalization of carbonyl compounds catalyzed by recyclable PVP-I
  作者：Di Wang、Fu-Rong Cao、Guangying Lu、Jiangmeng Ren、Bu-Bing Zeng

  DOI：10.1016/j.tet.2021.132250

  日期：2021.7

  A novel PVP-I catalyzed acetalizations/transacetalizations of carbonyl compounds has been developed processing with a mild and easy handling fashion. Different types of Acyclic and cyclic acetals were prepared from carbonyl compounds or their acetals successfully. Further applications of newly developed catalytic combination were testified. This protocol featured with simplicity of operation, mild

  已开发出一种新型 PVP-I 催化羰基化合物的缩醛化/转缩醛化，其处理方式温和且易于处理。以羰基化合物或其缩醛为原料成功制备了不同类型的无环和环状缩醛。证明了新开发的催化组合的进一步应用。该方案具有操作简单、反应条件温和、反应时间短、催化剂可回收利用、底物范围广、收率高等特点。
• Solvent-Less and Fluoride-Free Hiyama Reaction of Arylsiloxanes with Aryl Bromides and Chlorides Promoted by Sodium Hydroxide: A Useful Protocol for Palladium Recycling and Product Isolation
  作者：Emilio Alacid、Carmen Nájera

  DOI：10.1002/adsc.200505494

  日期：2006.5

  arylsiloxanes with aryl bromides and chlorides in low catalyst loading (0.001–0.1 mol % of Pd) under fluoride-free conditions to provide biaryls and heterobiaryls. For some deactivated aryl bromides and for aryl chlorides, the corresponding cross-couplings need TBAB as additive. Concentrated aqueous sodium hydroxide (50%) promoted this Hiyama reaction in practically the absence of solvents under air in good

  在无氟条件下，钯盐和肟衍生的palladacycles在低催化剂负载量（钯的0.001–0.1 mol％）下催化芳基硅氧烷与芳基溴化物和氯化物的交叉偶联反应，从而提供联芳基和杂联芳基。对于某些失活的芳基溴化物和芳基氯化物，相应的交叉偶联需要TBAB作为添加剂。在空气中几乎不存在溶剂的情况下，浓氢氧化钠水溶液（50％）促进了这种Hiyama反应，收率很高。该方法可以在压力管中加热或在微波辐射下于120℃下进行。该方案可实现钯的循环利用，并仅通过醚萃取就可促进最终产物的分离。