2-Chloro-3-(3-trifluoromethyl-phenyl)-propionaldehyde | 807667-31-8

• 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: 2-Chloro-3-(3-trifluoromethyl-phenyl)-propionaldehyde
• 英文别名: 2-Chloro-3-[3-(trifluoromethyl)phenyl]propanal
• CAS: 807667-31-8
• 化学式: C₁₀H₈ClF₃O
• 分子量: 236.621
• InChiKey: SRNYCKRPSZHQKF-UHFFFAOYSA-N

物化性质

• 沸点：
  236.4±35.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Chloro-3-(3-trifluoromethyl-phenyl)-propionaldehyde 在 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.5h， 生成 N-[5-(3-trifluoromethylbenzyl)-1,3-thiazol-2-yl]-4-chlorobenzamide
  参考文献：
  名称：

  Heterocyclic Syntheses on the Basis of Arylation Products of Unsaturated Compounds: X. 3-Aryl-2-chloropropanals as Reagents for the Synthesis of 2-Amino-1,3-thiazole Derivatives

  摘要：

  Meerwein reaction of arenediazonium chlorides with acrolein gave 3-aryl-2-chloropropanals which were brought into cyclocondensation with thiourea. The resulting 2-amino-5-benzyl-1,3-thiazoles were acylated with carboxylic acid chlorides and plithalic anhydride to afford, respectively, 2-acylamino-5-benzyl-1,3-thiazoles and N-(5-benzyl- 1,3-thiazol-2-yl)phthalimides.

  DOI：

  10.1023/b:rujo.0000034976.75646.85
• 作为产物：
  描述：

  3-(3-三氟甲基苯基)丙酸 在 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 戴斯-马丁氧化剂 、 L-脯氨酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-Chloro-3-(3-trifluoromethyl-phenyl)-propionaldehyde
  参考文献：
  名称：

  Carbene-Catalyzed α-Carbon Amination of Chloroaldehydes for Enantioselective Access to Dihydroquinoxaline Derivatives

  摘要：

  An NHC-catalyzed alpha-carbon amination of chloroaldehydes was developed. Cyclohexadiene-1,2-diimines are used as amination reagents and four-atom synthons. Our reaction affords optically enriched dihydroquinoxalines that are core structures in natural products and synthetic bioactive molecules.

  DOI：

  10.1021/acs.orglett.9b01520

文献信息

• Synthesis and BK channel-opening activity of 2-amino-1,3-thiazole derivatives
  作者：Xiao-Lei Qi、Heeji Jo、Xue-Ying Wang、Tong-Tong Ji、Hai-Xia Lin、Chul-Seung Park、Yong-Mei Cui

  DOI：10.1016/j.bmcl.2021.128083

  日期：2021.7

  activities in cell-based fluorescence assay and electrophysiological recording. The assay results indicated that the activities of the investigated compounds were influenced by the physicochemical properties of the substituent at benzene ring.

  合成了一系列 2-氨基-5-芳基甲基-或 5-杂芳基甲基-1,3-噻唑衍生物，并在基于细胞的荧光测定和电生理记录中评估了 BK 通道开放活动。测定结果表明，所研究化合物的活性受苯环取代基理化性质的影响。
• A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation
  作者：Zijun Wu、Jian Wang

  DOI：10.1039/c8sc04601h

  日期：——

  the carbene-catalyzed tandem dearomatization/rearomatization reaction of azonaphthalenes with α-chloroaldehydes is described. This protocol enables the efficient assembly of chiral dihydrocinnolinone derivatives in good yields with excellent enantioselectivities (up to 99% ee). Moreover, this strategy enables not only the highly enantioselective NHC-catalyzed nucleophilic aromatic substitution, but also

  在本研究中，描述了卡宾催化的偶氮萘与 α-氯醛的串联脱芳构化/重芳构化反应的第一个例子。该协议能够以优异的对映选择性（高达 99% ee）以良好的收率有效组装手性二氢肉桂酮衍生物。此外，该策略不仅可以实现高度对映选择性的 NHC 催化的亲核芳族取代，还可以形成正式的 Csp 2 -Csp 3键。
• Synthesis and antitumor activities of new N-(5-benzylthiazol-2-yl)-2-(heteryl-5-ylsulfanyl)-acetamides
  作者：Yu. V. Ostapiuk、D. A. Frolov、R. Ya. Vasylyschyn、V. S. Matiychuk

  DOI：10.7124/bc.000971

  日期：2018.2.28
• Bioisosteric replacement of 1H-1,2,3-triazole with 1H-tetrazole ring enhances anti-leukemic activity of (5-benzylthiazol-2-yl)benzamides
  作者：Nazariy Pokhodylo、Nataliya Finiuk、Olha Klyuchivska、Rostyslav Stoika、Vasyl Matiychuk、Mykola Obushak

  DOI：10.1016/j.ejmech.2023.115126

  日期：2023.3
• Heterocyclic Syntheses on the Basis of Arylation Products of Unsaturated Compounds: X. 3-Aryl-2-chloropropanals as Reagents for the Synthesis of 2-Amino-1,3-thiazole Derivatives
  作者：N. D. Obushak、V. S. Matiichuk、R. Ya. Vasylyshin、Yu. V. Ostapyuk

  DOI：10.1023/b:rujo.0000034976.75646.85

  日期：2004.3

  Meerwein reaction of arenediazonium chlorides with acrolein gave 3-aryl-2-chloropropanals which were brought into cyclocondensation with thiourea. The resulting 2-amino-5-benzyl-1,3-thiazoles were acylated with carboxylic acid chlorides and plithalic anhydride to afford, respectively, 2-acylamino-5-benzyl-1,3-thiazoles and N-(5-benzyl- 1,3-thiazol-2-yl)phthalimides.