2',3'-dichlorocinnamaldehyde | 1028206-40-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 2',3'-dichlorocinnamaldehyde
• 英文别名: 3-(2,3-Dichlorophenyl)acrylaldehyde；3-(2,3-dichlorophenyl)prop-2-enal
• CAS: 1028206-40-7
• 化学式: C₉H₆Cl₂O
• 分子量: 201.052
• InChiKey: DBEMJHDYRHMHEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2',3'-dichlorocinnamaldehyde 在 copper(I) oxide 、 sodium tetrahydroborate 、 potassium phosphate 、 溴 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 (4E)-4-[(2,3-dichlorophenyl)methylidene]-3-cyclohexyl-2-cyclohexyliminooxazolidine
  参考文献：
  名称：

  Formation of substituted 2-iminooxazolidines via intermolecular 1,2-addition/intramolecular N-vinylation using 3-substituted-2-bromo-2-propen-1-ols as substrates

  摘要：

  The Cu2O-catalyzed reaction between equimolar amounts of easily available 3-substituted-2-bromo-2-propen-1-ols and dicyclohexyl carbodiimide in DMSO at 100 degrees C using K3PO4 as the base and in the absence of any additive exclusively delivers substituted 2-iminooxazolidines with yields up to 80%. The highly selective transformation is assumed to start with an intermolecular 1,2-addition, which is followed by an intramolecular N-vinylation. The products can also be obtained in the absence of Cu2O, albeit in lower yields. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.08.051

文献信息

• Highly Enantioselective Catalytic Synthesis of Neurite Growth-Promoting Secoyohimbanes
  作者：Andrey P. Antonchick、Sara López-Tosco、Juan Parga、Sonja Sievers、Markus Schürmann、Hans Preut、Susanne Höing、Hans R. Schöler、Jared Sterneckert、Daniel Rauh、Herbert Waldmann

  DOI：10.1016/j.chembiol.2013.03.011

  日期：2013.4

  rhynchophylline, a highly enantioselective and efficient organocatalyzed synthesis method was developed that gives access to the tetracyclic secoyohimbane scaffold, embodying a quaternary and three tertiary stereogenic centers in a one-pot multistep reaction sequence. Investigation of a collection of the secoyohimbanes in primary rat hippocampal neurons and embryonal stem cell-derived motor neurons led

  具有神经调节活性的天然产物及其潜在的结构支架可能会激发新型神经营养化合物的合成。螺环七高辛烷生物碱茶碱是中药用于治疗中枢神经系统疾病的钩藤属植物提取物的主要成分。基于乙酰胆碱的结构，开发了一种高度对映体选择性和高效的有机催化合成方法，该方法可访问四环七代辛烷骨架，在一个多步反应序列中包含一个四级和三个三级立体异构中心。
• Enantioselective Organocatalytic Synthesis of a Secoyohimbane-Inspired Compound Collection with Neuritogenic Activity
  作者：Tim Förster、Sara López-Tosco、Slava Ziegler、Andrey P. Antonchick、Herbert Waldmann

  DOI：10.1002/cbic.201700015

  日期：2017.6.19

  the neuroprotective alkaloid rhynchophylline was synthesized employing a highly efficient enantioselective and organocatalyzed cascade process. Evaluation of the developed compound collection showed a family of neurotrophic compounds.

  中性神经脂多糖：利用高效的对映选择性和有机催化的级联过程合成了衍生自神经保护性生物碱类儿茶碱的螺环吲哚满酮文库。对开发的化合物集合的评估显示了神经营养化合物家族。
• Organocatalytic Asymmetric Formal [3+3] Cycloaddition Reactions of α,β-Unsaturated Aldehydes with Nazarov Reagents
  作者：Ming-Kui Zhu、Qiang Wei、Liu-Zhu Gong

  DOI：10.1002/adsc.200800174

  日期：2008.6.9

  An organocatalytic asymmetric formal [3+3] cycloaddition reaction of α,β-unsaturated aldehydes with Nazarov reagents promoted by prolinol derivatives afforded, after oxidation, 3,4-dihydropyranones in good yields with high enantioselectivities of up to 97% ee.

  α，β-不饱和醛与Nazarov试剂的有机催化不对称形式[3 + 3]环加成反应，由Prolinol衍生物促进，氧化后可提供高产率的3,4-二氢吡喃酮，对映选择性高达97％ee。
• Synthesis of Hexahydropyrrolo-isoquinolines by 1,3-Dipolar cycloaddition of tetrahydroisoquinolines and cinnamaldehydes
  作者：You-Gui Li、Wei-Ke Chen、You-Qiang Guo、Zhang Zhu、Jing-Jing Cao、Zhen-Yu Wang、Xiang Wu

  DOI：10.1016/j.tetlet.2023.154519

  日期：2023.6

  hexahydropyrrolo-isoquinolines through the 1,3-dipolar cycloaddition of cinnamaldehydes with azomethine ylides generated from cinnamaldehydes and tetrahydroisoquinolines. The carbonyl CO groups of cinnamaldehydes serve as the precursor for the generation of azomethine ylides and the CC double bonds of cinnamaldehyde act as the dipolarophiles in the cycloaddition. The key features are easily available substrates

  描述了一种通过肉桂醛与由肉桂醛和四氢异喹啉生成的偶氮甲碱叶立德进行 1,3-偶极环加成反应合成六氢吡咯并异喹啉的新方法。肉桂醛的羰基 C O 基团作为偶氮甲碱叶立德和 C肉桂醛的 C 双键在环加成中充当亲偶极试剂。主要特点是容易获得底物、良好的官能团耐受性和温和的反应条件。通过X射线单晶结构分析确定了产物的相关构型，并提出了可能的机理。进行了克级实验和一些化学转化以显示该方法的综合效用。最后，提出了一种似是而非的机制来阐明具有不同配置的产品的形成。
• Formation of substituted 2-iminooxazolidines via intermolecular 1,2-addition/intramolecular N-vinylation using 3-substituted-2-bromo-2-propen-1-ols as substrates
  作者：Heike Weischedel、Dietmar Schmidt、Jürgen Conrad、Uwe Beifuss

  DOI：10.1016/j.tet.2018.08.051

  日期：2018.11

  The Cu2O-catalyzed reaction between equimolar amounts of easily available 3-substituted-2-bromo-2-propen-1-ols and dicyclohexyl carbodiimide in DMSO at 100 degrees C using K3PO4 as the base and in the absence of any additive exclusively delivers substituted 2-iminooxazolidines with yields up to 80%. The highly selective transformation is assumed to start with an intermolecular 1,2-addition, which is followed by an intramolecular N-vinylation. The products can also be obtained in the absence of Cu2O, albeit in lower yields. (C) 2018 Elsevier Ltd. All rights reserved.