2-chloro-3-(4-fluorophenyl)propanal | 807667-29-4

• 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-(4-fluorophenyl)propanal
• CAS: 807667-29-4
• 化学式: C₉H₈ClFO
• 分子量: 186.613
• InChiKey: BNWSWVNNRPJNIY-UHFFFAOYSA-N

物化性质

• 沸点：
  238.7±25.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-3-(4-fluorophenyl)propanal 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-(4-fluorobenzyl)-1,3-thiazol-2-yl]acetamide
  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-(4-氟苯基)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-(4-fluorophenyl)propanal
  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

• [EN] COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS ET LEURS UTILISATIONS
  申请人：YUMANITY THERAPEUTICS INC

  公开号：WO2020198026A1

  公开（公告）日：2020-10-01

  The present invention features compounds useful in the treatment of neurological disorders and primary brain cancer. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders and primary brain cancer.

  本发明涉及对神经系统疾病和原发性脑癌治疗中有用的化合物。本发明的化合物，单独或与其他药用活性剂结合使用，可用于治疗或预防神经系统疾病和原发性脑癌。
• [EN] ANTI-HIV COMPOUNDS<br/>[FR] COMPOSÉS ANTI-VIH
  申请人：PANACOS PHARMACEUTICALS INC

  公开号：WO2009085256A1

  公开（公告）日：2009-07-09

  Thiazole derivatives represented by Formula (I) are disclosed, where R1, R2, R3, A, X, Y, Z, R6 and R7 are disclosed herein. These thiazole derivatives and pharmaceutical compositions comprising these derivatives are useful in the treatment of HIV mediated diseases and conditions.

  公式（I）代表的噻唑衍生物已被披露，其中在此披露了R1、R2、R3、A、X、Y、Z、R6和R7。这些噻唑衍生物和包含这些衍生物的药物组合物在治疗HIV介导的疾病和症状方面是有用的。
• Stereoselective [8 + 2] Cycloaddition Reaction of Azaheptafulvenes with α-Chloro Aldehydes via N-Heterocyclic Carbene Catalysis
  作者：Chonglong He、Zhanhuan Li、Hongwei Zhou、Jianfeng Xu

  DOI：10.1021/acs.orglett.9b03014

  日期：2019.10.4

  A highly efficient [8 + 2] cycloaddition reaction of azaheptafulvenes with α-chloro aliphatic aldehydes enabled by N-heterocyclic carbene catalysis is presented, delivering cis-cycloheptatriene-fused γ-lactams with good yields, moderate to good diastereoselectivies, and excellent enantioselectivies. This higher order cycloaddition reaction can be readily expanded to the gram scale, and the products

  氮杂七烯酮与N-杂环卡宾催化的α-氯脂肪族醛的高效[8 + 2]环加成反应被提出，以高收率，中等至良好的非对映选择性和优异的对映选择性提供顺式-环庚三烯稠合的γ-内酰胺。该高阶环加成反应可以容易地扩展至克级，并且可以通过简单的操作将产物进一步转化为其他有用的化合物。
• Discovery and Potency Optimization of 2-Amino-5-arylmethyl-1,3-thiazole Derivatives as Potential Therapeutic Agents for Prostate Cancer
  作者：Mikhail Krasavin、Ruben Karapetian、Igor Konstantinov、Yuri Gezentsvey、Konstantin Bukhryakov、Elena Godovykh、Olga Soldatkina、Yan Lavrovsky、Andrei V. Sosnov、Andrei A. Gakh

  DOI：10.1002/ardp.200800201

  日期：2009.7

  antiproliferative activity on DU‐145 human prostate carcinoma cell line (hit compound potency – 2.9 μM). Medicinal chemistry optimization of two peripheral diversity vectors of the hit molecule, independently, led to SAR generalizations and identification of the ‘best’ moieties. The latter were merged in a single compound that exhibited an over 100‐fold better potency than the hit compound. For the most potent

  通过高通量筛选确定了一个新的化学系列，它对 DU-145 人前列腺癌细胞系具有抗增殖活性（命中化合物效力 - 2.9 μM）。对命中分子的两个外围多样性载体的药物化学优化，独立地导致 SAR 概括和“最佳”部分的鉴定。后者合并为单一化合物，其效力比命中化合物高 100 倍以上。对于最有效的化合物，已证实观察到的抗增殖效力与化合物的非特异性细胞毒性无关。
• Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and <i>o</i>-Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins
  作者：Xingkuan Chen、Runjiang Song、Yingguo Liu、Chong Yih Ooi、Zhichao Jin、Tingshun Zhu、Hongling Wang、Lin Hao、Yonggui Robin Chi

  DOI：10.1021/acs.orglett.7b02883

  日期：2017.11.3

  A highly enantioselective method for quick access to dihydrocoumarins is reported. The reaction involves a cooperative catalytic process with carbene and in situ generated Brønsted acid as the catalysts. α-Chloro aldehyde and readily available and stable o-hydroxybenzhydryl amine substrates were used to generate reactive azolium ester enolate and ortho-quinone methide (o-QM) intermediates, respectively

  报道了一种快速对映二氢香豆素的高度对映选择性的方法。该反应涉及使用卡宾和原位生成的布朗斯台德酸作为催化剂的协同催化过程。使用α-氯醛和易于获得且稳定的邻羟基苯甲胺底物分别生成反应性的氮鎓烯醇酯烯醇盐和邻醌甲基化物（o- QM）中间体，以形成具有极高非对映选择性和对映选择性的二氢香豆素。催化反应产物可以容易地转化为有价值的药物和生物活性分子。