ethyl 3-(2,4,5-trifluorophenyl)acrylate | 888321-36-6

• 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: ethyl 3-(2,4,5-trifluorophenyl)acrylate
• 英文别名: ethyl 3-(2,4,5-trifluorophenyl)prop-2-enoate
• CAS: 888321-36-6
• 化学式: C₁₁H₉F₃O₂
• 分子量: 230.186
• InChiKey: AODMFHNJISFCRH-UHFFFAOYSA-N

物化性质

• 沸点：
  262.5±35.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2,4,5-trifluorophenyl)acrylate 在 palladium 10% on activated carbon 、 氢气 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 3-(2,4,5-三氟苯基)丙酸
  参考文献：
  名称：

  （的简明对映选择性合成- [R）-selegiline，（小号）-benzphetamine和正式合成（- [R ）手性通过酰亚胺烯醇化物的电叠氮化-sitagliptin

  摘要：

  简明和（的高产对映选择性合成- [R）-selegiline，抗帕金森氏药，（小号）-benzphetamine，抗肥胖剂，以及（小号）-sitagliptin，抗糖尿病药物已经描述从市售起始可用的原料采用Evans手性酰亚胺烯酸酯的亲电子叠氮化作为关键的手性诱导步骤，该步骤以非对映选择性高的方式进行（> 99％）。

  DOI：

  10.1016/j.tetasy.2014.11.014
• 作为产物：
  描述：

  乙氧甲酰基亚甲基三苯基膦 、 2,4,5-三氟苯甲醛 以 苯 为溶剂， 以98%的产率得到ethyl 3-(2,4,5-trifluorophenyl)acrylate
  参考文献：
  名称：

  （的简明对映选择性合成- [R）-selegiline，（小号）-benzphetamine和正式合成（- [R ）手性通过酰亚胺烯醇化物的电叠氮化-sitagliptin

  摘要：

  简明和（的高产对映选择性合成- [R）-selegiline，抗帕金森氏药，（小号）-benzphetamine，抗肥胖剂，以及（小号）-sitagliptin，抗糖尿病药物已经描述从市售起始可用的原料采用Evans手性酰亚胺烯酸酯的亲电子叠氮化作为关键的手性诱导步骤，该步骤以非对映选择性高的方式进行（> 99％）。

  DOI：

  10.1016/j.tetasy.2014.11.014

文献信息

• Desulfurative Chlorination of Alkyl Phenyl Sulfides
  作者：Daniele Canestrari、Stefano Lancianesi、Eider Badiola、Chiara Strinna、Hasim Ibrahim、Mauro F. A. Adamo

  DOI：10.1021/acs.orglett.7b00077

  日期：2017.2.17

  The chlorination of readily available secondary and tertiary alkyl phenyl sulfides using (dichloroiodo)benzene (PhICl2) is reported. This mild and rapid nucleophilic chlorination is extended to sulfa-Michael derived sulfides, affording elimination-sensitive β-chloro carbonyl and nitro compounds in good yields. The chlorination of enantioenriched benzylic sulfides to the corresponding inverted chlorides

  报道了使用（二氯碘代）苯（PhICl 2）对易得的仲和叔烷基苯基硫化物进行氯化。这种温和而快速的亲核氯化作用扩展到了磺胺-迈克尔衍生的硫化物，从而以高收率提供了对消除敏感的β-氯羰基和硝基化合物。将对映体富集的苄基硫化物氯化为相应的倒置氯化物，其立体定向性很高，因此可以正式进入对映体富集的氯-迈克尔加合物。这意味着一个二氯λ的地层中的装置4提出-sulfurane中间。
• Discovery of 3-aminopiperidines as potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitors
  作者：Jason M. Cox、Bart Harper、Anthony Mastracchio、Barbara Leiting、Ranabir Sinha Roy、Reshma A. Patel、Joseph K. Wu、Kathryn A. Lyons、Huaibing He、Shiyao Xu、Bing Zhu、Nancy A. Thornberry、Ann E. Weber、Scott D. Edmondson

  DOI：10.1016/j.bmcl.2007.05.087

  日期：2007.8

  Substituted 3-aminopiperidines 3 were evaluated as DPP-4 inhibitors. The inhibitors showed good DPP-4 potency with superb selectivity over other peptidases (QPP, DPP8, and DPP9). Selected DPP-4 inhibitors were further evaluated for their hERG potassium channel, calcium channel, Cyp2D6, and pharmacokinetic profiles.

  评价取代的3-氨基哌啶3作为DPP-4抑制剂。与其他肽酶（QPP，DPP8和DPP9）相比，该抑制剂具有良好的DPP-4效力和极高的选择性。进一步评估了选定的DPP-4抑制剂的hERG钾通道，钙通道，Cyp2D6和药代动力学特征。
• Fused Aminopiperidines as Dipeptidyl Peptidase-4 Inhibitors for the Treatment or Prevention of Diabetes
  申请人：Cox Jason M.

  公开号：US20090233936A1

  公开（公告）日：2009-09-17

  The present invention is directed to novel substituted fused aminopiperidines of structural formula (I) which are inhibitors of the dipeptidyl peptidase-4 enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-4 enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-4 enzyme is involved.

  本发明涉及一种新颖的结构式（I）的取代融合氨基哌啶，其是二肽基肽酶-4酶的抑制剂，并且在治疗或预防二肽基肽酶-4酶参与的疾病中，例如糖尿病和特别是2型糖尿病中有用。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在预防或治疗二肽基肽酶-4酶参与的这些疾病中的使用。
• Aminopiperidines as Dipeptidyl Peptidase-IV Inhibitors for the Treatment or Prevention of Diabetes
  申请人：Cox M. Jason

  公开号：US20080076773A1

  公开（公告）日：2008-03-27

  The present invention is directed to novel substituted aminopiperidines which are inhibitors of the dipeptidyl peptidase-IV enzyme (“DPP-IV inhibitors”) and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及一种新型的取代氨基哌啶，它是二肽基肽酶-IV酶（“DPP-IV酶”）的抑制剂，并且在治疗或预防DPP-IV酶参与的疾病，如糖尿病，尤其是2型糖尿病方面具有用处。本发明还涉及包含这些化合物的制药组合物，以及使用这些化合物和组合物在预防或治疗DPP-IV酶参与的这些疾病方面的用途。
• Fused Aminopiperidines as Dipeptidyl Peptidase-IV Inhibitors for the Treatment or Prevention of Diabetes
  申请人：Cox Jason M.

  公开号：US20090258894A1

  公开（公告）日：2009-10-15

  The present invention is directed to novel substituted fused aminopiperidines which are inhibitors of the dipeptidyl peptidase-IV enzyme (“DPP-IV inhibitors”) and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及新型取代融合氨基哌啶类化合物，其为二肽基肽酶-IV酶（“DPP-IV抑制剂”）的抑制剂，可用于治疗或预防二肽基肽酶-IV酶涉及的疾病，例如糖尿病，特别是2型糖尿病。本发明还涉及包含这些化合物的制药组合物以及在预防或治疗二肽基肽酶-IV酶涉及的这些疾病中使用这些化合物和组合物。