Tert-butyl 3-(3-fluorophenyl)prop-2-enoate | 862499-31-8

• 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: Tert-butyl 3-(3-fluorophenyl)prop-2-enoate
• CAS: 862499-31-8
• 化学式: C₁₃H₁₅FO₂
• 分子量: 222.259
• InChiKey: IKDGGSOWHJECTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Tert-butyl 3-(3-fluorophenyl)prop-2-enoate 、 (S)-(-)-N-苄基-1-苯基-乙胺 在 正丁基锂 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以83%的产率得到tert-butyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-(3'-fluorophenyl)propanoate
  参考文献：
  名称：

  Asymmetric synthesis of syn- and anti-α-deuterio-β3-phenylalanine derivatives

  摘要：

  The conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of aryl substituted tert-butyl cinnamate esters followed by reaction of the resultant lithium beta-amino enolates with D2O provides access to anti configured alpha-deuterio-beta-aminocinnamate esters in high dr. The corresponding syn configured diastereoisomers were also obtained with high diastereoselectivity via the conjugate addition of lithium (5)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of tert-butyl alpha-deuteriocinnamate esters followed by reaction of the resultant lithium beta-amino enolates with 2-pyridone. After deprotection both the syn- and anti-diastereoisomers of the corresponding alpha-deuterio-beta(3)-amino acids can be isolated in high dr. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.008
• 作为产物：
  描述：

  丙烯酸叔丁酯 、 间氟碘苯 在 sodium formate 、 palladium diacetate 、 potassium carbonate 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以100%的产率得到Tert-butyl 3-(3-fluorophenyl)prop-2-enoate
  参考文献：
  名称：

  Poly(ethylene glycol) as reaction medium for mild Mizoroki–Heck reaction in a ball-mill

  摘要：

  无磷烯的钯催化Mizoroki–Heck反应是在聚乙烯醇的球磨条件下进行的，反应条件温和。得到了良好至优异的耦合产物产率。这种活化技术还促进了圆形Pd–PEG纳米颗粒的同时形成，并通过透射电子显微镜（TEM）分析进行了表征。

  DOI：

  10.1039/c2cc36286d

文献信息

• Poly(ethylene glycol) as reaction medium for mild Mizoroki–Heck reaction in a ball-mill
  作者：Valérie Declerck、Evelina Colacino、Xavier Bantreil、Jean Martinez、Frédéric Lamaty

  DOI：10.1039/c2cc36286d

  日期：——

  Phosphine-free palladium-catalyzed Mizoroki–Heck reaction was performed using ball-milling in polyethylene glycol under mild conditions. Good to excellent yields of coupling products were obtained. This activation technique also allowed the concomitant formation of round shaped Pd–PEG nanoparticles that were characterized by TEM analysis.

  无磷烯的钯催化Mizoroki–Heck反应是在聚乙烯醇的球磨条件下进行的，反应条件温和。得到了良好至优异的耦合产物产率。这种活化技术还促进了圆形Pd–PEG纳米颗粒的同时形成，并通过透射电子显微镜（TEM）分析进行了表征。
• Asymmetric synthesis of syn- and anti-α-deuterio-β3-phenylalanine derivatives
  作者：Stephen G. Davies、Emma M. Foster、Catherine R. McIntosh、Paul M. Roberts、Timothy E. Rosser、Andrew D. Smith、James E. Thomson

  DOI：10.1016/j.tetasy.2011.06.008

  日期：2011.5

  The conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of aryl substituted tert-butyl cinnamate esters followed by reaction of the resultant lithium beta-amino enolates with D2O provides access to anti configured alpha-deuterio-beta-aminocinnamate esters in high dr. The corresponding syn configured diastereoisomers were also obtained with high diastereoselectivity via the conjugate addition of lithium (5)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of tert-butyl alpha-deuteriocinnamate esters followed by reaction of the resultant lithium beta-amino enolates with 2-pyridone. After deprotection both the syn- and anti-diastereoisomers of the corresponding alpha-deuterio-beta(3)-amino acids can be isolated in high dr. (C) 2011 Elsevier Ltd. All rights reserved.