(Z/E) methyl 3-(2,5-difluorophenyl)acrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z/E) methyl 3-(2,5-difluorophenyl)acrylate
• 英文别名: Adam’s catalyst；Methyl (E)-3-(2,5-difluorophenyl)acrylate；methyl 3-(2,5-difluorophenyl)prop-2-enoate
• 化学式: C₁₀H₈F₂O₂
• 分子量: 198.169
• InChiKey: UWDJYEPPOANSLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z/E) methyl 3-(2,5-difluorophenyl)acrylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以90%的产率得到(Z/E) 3-(2,5-difluorophenyl)acrylic acid
  参考文献：
  名称：

  Synthesis of Z‐N‐Alkenylformamides

  摘要：

  Commercially available difluorinated benzaldehyde was converted to the Z-N-alkenylformamides via Horner-Emmons olefination and Curtius rearrangement, followed by reduction with tri-tert-butoxy-aluminohydride.

  DOI：

  10.1080/00397910701649023
• 作为产物：
  描述：

  膦酰基乙酸甲酯二乙酯 、 2,5-二氟苯甲醛 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 生成 (Z/E) methyl 3-(2,5-difluorophenyl)acrylate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel aminomethyl-piperidones based DPP-IV inhibitors

  摘要：

  A series of novel aminomethyl-piperidones were designed and evaluated as potential DPP-IV inhibitors. Optimized analogue 12v ((4S, 5S)-5-(aminomethyl)-1-(2-(benzo[d][1,3] dioxol-5-yl) ethyl)-4-(2,5-difluorophenyl) piperidin-2-one) showed excellent in vitro potency and selectivity for DPP-IV over other serine proteases. The lead compound 12v showed potent and long acting antihyperglycemic effects (in vivo), along with improved pharmacokinetic profile. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.009

文献信息

• Tricyclic Nitrogen Containing Compounds And Their Use As Antibacterials
  申请人：Alemparte-Gallardo Carlos

  公开号：US20110071155A1

  公开（公告）日：2011-03-24

  Compounds of Formula (I) or pharmaceutically acceptable salts or N-oxides thereof: wherein: one of Z 1 and Z 2 is CH or N and the other is CH; L is selected from: —CH 2 —CH═CH—, —CH═CH—CH 2 —, —(CH 2 ) p — where p is 2, 3 or 4, —CH 2 —CH 2 —O—, —O—CH 2 —CH 2 —, —CH 2 —CH 2 —NH—, —HN—CH 2 —CH 2 —, —C(O)—CH═CH—, —CH═CH—C(O)—, —CH 2 —C≡C— or —C≡C—CH 2 —; U represents a cyclic group; m is 0 or 1, n is independently 0 or 1; and substituent(s) R 5 and R 6 are independently selected from: halo, CF 3 , OCF 3 , C 1-3 alkyl, C 1-3 alkoxy, nitro and cyano, pharmaceurtical compositions comprising them, their use in therapy especially against tuberculosis, and methods of preparing them.

  化合物式（I）或其药学上可接受的盐或N-氧化物的化合物： 其中： Z1和Z2中的一个为CH或N，另一个为CH； L选择自：—CH2—CH═CH—，—CH═CH—CH2—，—（CH2）p—，其中p为2、3或4，—CH2—CH2—O—，—O—CH2—CH2—，—CH2—CH2—NH—，—HN—CH2—CH2—，—C（O）—CH═CH—，—CH═CH—C（O）—，—CH2—C≡C—或—C≡C—CH2—； U代表一个环状基团； m为0或1，n独立地为0或1； 取代基R5和R6分别选择自：卤素，CF3，OCF3，C1-3烷基，C1-3烷氧基，硝基和氰基。 包括它们的药物组合物，尤其是用于治疗结核病的药物组合物，以及制备它们的方法。
• TRICYCLIC COMPOUNDS AS ANTIBACTERIALS
  申请人：Pearson Neil David

  公开号：US20100137353A1

  公开（公告）日：2010-06-03

  Tricyclic nitrogen containing compounds and their use as antibacterials.

  三环氮含化合物及其作为抗菌剂的用途。
• Design, Synthesis of (±)‐Millpuline A, and Biological Evaluation for the Lung Cell Protective Effects through SRC
  作者：Heng Zhang、Xiao Guo、Di Zhou、Jiatong Wen、Yingzhan Tang、Jian Wang、Yang Liu、Gang Chen、Ning Li

  DOI：10.1002/cmdc.202300219

  日期：2023.10.17

  We report a visible-light-induced intermolecular [2+2] photocycloaddition reaction based on flavonoids to synthesize (±)-millpuline A and 20 derivatives (B1–B20), which could be constructed to address the problems of low yield, poor physicochemical properties, and lack of target definition in total synthesis of complex natural products.

  我们报道了基于黄酮类化合物的可见光诱导分子间[2+2]光环加成反应合成(±)-millpuline A和20个衍生物( B1 – B20 )，该反应可以解决收率低、理化差的问题性质，以及复杂天然产物全合成中缺乏目标定义。
• TRICYCLIC NITROGEN CONTAINING COMPOUNDS AND THEIR USE AS ANTIBACTERIALS
  申请人：Glaxo Group Limited

  公开号：EP2300477A1

  公开（公告）日：2011-03-30
• Design, synthesis and biological evaluation of novel aminomethyl-piperidones based DPP-IV inhibitors
  作者：Pradip Jadav、Rajesh Bahekar、Shailesh R. Shah、Dipam Patel、Amit Joharapurkar、Mukul Jain、Kalapatapu V.V.M. Sairam、Praveen Kumar Singh

  DOI：10.1016/j.bmcl.2014.03.009

  日期：2014.4

  A series of novel aminomethyl-piperidones were designed and evaluated as potential DPP-IV inhibitors. Optimized analogue 12v ((4S, 5S)-5-(aminomethyl)-1-(2-(benzo[d][1,3] dioxol-5-yl) ethyl)-4-(2,5-difluorophenyl) piperidin-2-one) showed excellent in vitro potency and selectivity for DPP-IV over other serine proteases. The lead compound 12v showed potent and long acting antihyperglycemic effects (in vivo), along with improved pharmacokinetic profile. (c) 2014 Elsevier Ltd. All rights reserved.