3,5-双(三氟甲基)肉桂酸 | 503179-72-4

• 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
• 中文名称: 3,5-双(三氟甲基)肉桂酸
• 英文名称: 3,5-bis(trifluoromethyl) cinnamic acid
• 英文别名: 3-[3,5-bis(trifluoromethyl)phenyl]prop-2-enoic Acid
• CAS: 503179-72-4
• 化学式: C₁₁H₆F₆O₂
• 分子量: 284.158
• InChiKey: IZKCKOPHMWHBHR-UHFFFAOYSA-N

物化性质

• 沸点：
  273.9±35.0 °C(Predicted)
• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-双(三氟甲基)肉桂酸 在 N,N-二甲基甲酰胺 草酰氯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以100%的产率得到3,5-bis(trifluoromethyl)cinnamoyl chloride
  参考文献：
  名称：

  WO2008/74755

  摘要：

  公开号：
• 作为产物：
  描述：

  丙二酸 、 3,5-双三氟甲基苯甲醛 在 哌啶 、 吡啶 作用下， 反应 2.0h， 生成 3,5-双(三氟甲基)肉桂酸
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel diarylalkyl amides as TRPV1 antagonists

  摘要：

  We have developed a new class of diarylalkyl amides as novel TRPV1 antagonists. They exhibited potent Ca-45(2+) uptake inhibitions in rat DRG neuron. In particular, the amide 59 was identified as a potent antagonist with IC50 of 57 nM. The synthesis and structure-activity relationship of the diarylalkyl amides are also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.010

文献信息

• Enantioselective 1,4‐Addition Reaction of α,β‐Unsaturated Carboxylic Acids with Cycloalkanones Using Cooperative Chiral Amine–Boronic Acid Catalysts
  作者：Takahiro Horibe、Takashi Hazeyama、Yuto Nakata、Kazuki Takeda、Kazuaki Ishihara

  DOI：10.1002/anie.202007639

  日期：2020.9.21

  An enantioselective 1,4‐addition of α,β‐unsaturated carboxylic acids with cycloalkanones has been developed by using chiral amine–boronic acid cooperative catalysts. In the presence of a chiral amine and boronic acid, cycloalkanones and carboxylic acids are activated as chiral enamines and mixed anhydrides, respectively. The corresponding 1,4‐adducts are obtained in high yield with high enantioselectivity

  通过使用手性胺-硼酸协同催化剂，已经开发出了α，β-不饱和羧酸与环烷酮的对映选择性1,4加成反应。在手性胺和硼酸的存在下，环烷酮和羧酸分别被活化为手性烯胺和混合酸酐。相应的1,4加合物以高收率和高对映选择性获得。此外，随后的1,4加合物的氧化内酯化作用使螺内酯具有非对映选择性高。
• Mining Plants for Bacterial Quorum Sensing Modulators
  作者：Shimrit David、Aviad Mandabi、Shaked Uzi、Asaph Aharoni、Michael M. Meijler

  DOI：10.1021/acschembio.7b00859

  日期：2018.1.19

  uses quorum sensing (QS) in order to regulate the transfer of DNA into the host plant genome, and this results in the induction of crown gall tumors. The deleterious results of these infections are widespread and affect many species of fruit and crops. In order to further our understanding of this process and to provide potential solutions, we evaluated a library of 3800 natural products from plant

  细菌植物病原体根癌农杆菌使用群体感应（QS）来调节DNA向宿主植物基因组中的转移，从而导致冠状胆囊肿瘤的诱导。这些感染的有害结果广泛存在，并影响许多种类的水果和农作物。为了进一步了解该过程并提供可能的解决方案，我们评估了一个来自植物的3800种天然产物的库，并确定了能够强烈调节植物与细菌相互作用的有效化合物。
• Unnatural Polyketide Analogues Selectively Target the HER Signaling Pathway in Human Breast Cancer Cells
  作者：Seok Joon Kwon、Moon Il Kim、Bosung Ku、Lydie Coulombel、Jin-Hwan Kim、Joseph H. Shawky、Robert J. Linhardt、Jonathan S. Dordick

  DOI：10.1002/cbic.200900674

  日期：2010.3.1

  Multiple HER TK inhibitor: In vitro precursor‐directed syntheses of polyketide analogues resulted in the identification of several “unnatural” natural products that suppressed the HER‐PI3K‐Akt signaling pathway, as well as having multiple HER TK inhibitory activity.

  多种 HER TK 抑制剂：聚酮化合物类似物的体外前体定向合成导致鉴定了几种抑制 HER-PI3K-Akt 信号通路以及具有多种 HER TK 抑制活性的“非天然”天然产物。
• Therapeutic agent for Parkinson's disease
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US05484920A1

  公开（公告）日：1996-01-16

  Agents for the treatment of Parkinson's disease contain, as an active ingredient, a xanthine derivative or a pharmaceutically acceptable salt thereof. The xanthine derivative is represented by the formula: ##STR1## in which R.sup.1, R.sup.2 are R.sup.3 are independently hydrogen, lower alkyl, lower alkenyl, or lower alkynyl; and R.sup.4 represents cycloalkyl, --(CH.sub.2).sub.n --R.sup.5 (in which R.sup.5 represents substituted or unsubstituted aryl or a substituted or unsubstituted heterocyclic group; and n is an integer of 0 to 4), or ##STR2## in which Y.sup.1 and Y.sup.2 represent independently hydrogen, halogen, or lower alkyl; and Z represents substituted or unsubstituted aryl, ##STR3## in which R.sup.6 represents hydrogen, hydroxy, lower alkyl, lower alkoxy, halogen, nitro, or amino; and m represents an integer of 1 to 4, or a substituted or unsubstituted heterocyclic group; and X.sup.1 and X.sup.2 represent independently O or S.

  帕金森病的治疗剂含有黄嘌呤衍生物或其药学上可接受的盐作为活性成分。黄嘌呤衍生物由以下式子表示：##STR1## 其中R.sup.1、R.sup.2和R.sup.3分别表示氢、低碳基、低烯基或低炔基；而R.sup.4表示环烷基、--(CH.sub.2).sub.n --R.sup.5（其中R.sup.5表示取代或未取代的芳基或取代或未取代的杂环基；n为0到4的整数），或##STR2## 其中Y.sup.1和Y.sup.2分别表示氢、卤素或低碳基；而Z表示取代或未取代的芳基，##STR3## 其中R.sup.6表示氢、羟基、低碳基、低烷氧基、卤素、硝基或氨基；m表示1到4的整数，或取代或未取代的杂环基；而X.sup.1和X.sup.2分别表示氧或硫。
• Antidepressants
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US05543415A1

  公开（公告）日：1996-08-06

  The present invention relates to an antidepressant containing as an active ingredient a xanthine derivative or a pharmaceutically acceptable salt thereof, the xanthine derivative being represented by Formula (I) : ##STR1## in which R.sup.1, R.sup.2, and R.sup.3 represent independently hydrogen, lower alkyl, lower alkenyl; R.sup.4 represents cycloalkyl, --(CH.sub.2).sub.n --R.sup.5 (in which R.sup.5 represents substituted or unsubstituted aryl or a substituted or unsubstituted heterocyclic group; and n is an integer of 0 to 4), or ##STR2## (in which Y.sup.1 and Y.sup.2 represent independently hydrogen, halogen or lower alkyl; and Z represents substituted or unsubstituted aryl, ##STR3## (in which R.sup.6 represents hydrogen, hydroxy, lower alkyl, lower alkoxy, halogen, nitro, or amino; and m represents an integer of 1 to 3), or a substituted or unsubstituted heterocyclic group); and X.sup.1 and X.sup.2 represent independently O or S.

  本发明涉及一种抗抑郁剂，其活性成分为黄嘌呤衍生物或其药学上可接受的盐，该黄嘌呤衍生物由式(I)表示： ##STR1## 其中R.sup.1，R.sup.2和R.sup.3分别独立表示氢，低烷基，低烯基；R.sup.4表示环烷基，--(CH.sub.2).sub.n --R.sup.5（其中R.sup.5表示取代或未取代的芳基或取代或未取代的杂环基；n为0至4的整数），或##STR2##（其中Y.sup.1和Y.sup.2分别独立表示氢，卤素或低烷基；Z表示取代或未取代的芳基，##STR3##（其中R.sup.6表示氢，羟基，低烷基，低烷氧基，卤素，硝基或氨基；m表示1至3的整数），或取代或未取代的杂环基）；X.sup.1和X.sup.2分别独立表示O或S。