(E)-3-(2-fluorophenyl)-2-methylacrylaldehyde | 1375800-37-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (E)-3-(2-fluorophenyl)-2-methylacrylaldehyde
• 英文别名: (E)-3-(2-Fluorophenyl)-2-methylacrylaldehyde；(E)-3-(2-fluorophenyl)-2-methylprop-2-enal
• CAS: 1375800-37-5
• 化学式: C₁₀H₉FO
• 分子量: 164.179
• InChiKey: BEYJLWPCKXPANB-SOFGYWHQSA-N

物化性质

• 沸点：
  253.9±15.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P501,P210,P264,P280,P302+P352,P370+P378,P337+P313,P305+P351+P338,P362+P364,P332+P313,P403+P235
• 危险性描述：
  H315,H319,H227
• 储存条件：
  存储条件：密封、干燥，并在惰性气体环境中于2-8°C下保存。

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-fluorophenyl)-2-methylacrylaldehyde 在 sodium tetrahydroborate 、 sodium sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 25.17h， 生成 (E)-3-(2-fluorophenyl)-2-methyl-N-(2-(1-methylpyrrolidin-2-yl)ethyl)prop-2-en-1-amine
  参考文献：
  名称：

  Synthesis, modeling and functional activity of substituted styrene-amides as small-molecule CXCR7 agonists

  摘要：

  The chemokine receptor CXCR7 is an atypical G protein-coupled receptor as it preferentially signals through the beta-arrestin pathway rather than through G proteins. CXCR7 is thought to be of importance in cancer and the development of CXCR7-targeting ligands is of huge importance to further elucidate the pharmacology and the therapeutic potential of CXCR7. In the present study, we synthesized 24 derivatives based on a compound scaffold patented by Chemocentryx and obtained CXCR7 ligands with pK(i) values ranging from 5.3 to 8.1. SAR studies were supported by computational 3D Fingerprint studies, revealing several important affinity descriptors. Two key compounds (29 and 30, VUF11207 and VUF11403) were found to be high-potency ligands that induce recruitment of beta-arrestin2 and subsequent internalization of CXCR7, making them important tool compounds in future CXCR7 research. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.041
• 作为产物：
  描述：

  2-氟苯甲醛 在 sodium hydride 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 mineral oil 为溶剂， 反应 44.0h， 生成 (E)-3-(2-fluorophenyl)-2-methylacrylaldehyde
  参考文献：
  名称：

  氢键供体/路易斯酸共催化对映选择性质子转移未活化二烯酮的不对称纳扎罗夫环化

  摘要：

  我们报道了手性氢键供体与甲硅烷基路易斯酸共同催化的对映选择性纳扎罗夫环化。所开发的转化可以从各种简单的未活化二烯酮中获得高水平对映选择性（高达 95% ee）的三取代环戊烯酮。动力学和机理研究与可逆 4π 电环化 C−C 键形成步骤一致，随后以速率和对映体决定质子转移作为催化模式。

  DOI：

  10.1002/adsc.202000831

文献信息

• Hydrazide Compounds for Combating Animal Pests
  申请人：Hofmann Michael

  公开号：US20070265231A1

  公开（公告）日：2007-11-15

  The present invention relates to new hydrazide compounds which are useful for combating animal pests, in particular insects, arachnids and nematodes and to the salts thereof. The invention also relates to a method for combating insects, nematodes and arachnids. The hydrazide compounds of the invention are described by the general formula (I) wherein . . . is absent or a covalent bond; A is an optionally substituted cyclic radical selected from phenyl, naphthyl and a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are selected, independently of one another, from O, N and S, the 5- or 6-membered heterocyclic radical may have a carbonyl group as ring member; Q is selected from the group consisting of a single bond, C 1 -C 4 alkylidene, O—-C 1 -C 4 alkylidene, S—C 1 -C 4 alkylidene and NR 9 —C 1 -C 4 alkylidene, wherein the alkylidene group in the last four mentioned radicals is unsubstituted or carries 1, 2, 3 or 4 substituents selected from OH, ═O, halogen, C 1 -C 4 haloalkyl and C 1 -C 4 alkoxy; or A-Q may together be C 1 -C 10 -alkyl, which may be substituted by 1 or 2 substituents selected from the group consisting of ═O, OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, halogen or C 1 -C 4 -alkylcarbonyloxy, X is C═O, C═S or SO 2 ; Ar is an optionally substituted aromatic radical selected from phenyl, naphthyl, pyridyl, pyrimidyl, furyl and thienyl; and R 1 to R 6 and R 9 are as described in the claims and the specification.

  本发明涉及一种新的腙酰肼类化合物及其盐，其可用于对抗动物害虫，特别是昆虫、蜘蛛和线虫。本发明还涉及一种对抗昆虫、线虫和蜘蛛的方法。本发明中的腙酰肼化合物由一般式(I)描述，其中...为空或为共价键；A是选自苯基、萘基和带有1至4个杂原子（独立于彼此）的5-或6-成员杂环基，所述杂原子选自O、N和S，5-或6-成员杂环基可以具有一个环成员为羰基基团；Q选自单键、C1-C4烷基亚甲基、O-C1-C4烷基亚甲基、S-C1-C4烷基亚甲基和NR9-C1-C4烷基亚甲基的群，其中最后四个提到的基中的烷基亚甲基基团未被取代或携带1、2、3或4个取代基，所述取代基选自OH、═O、卤素、C1-C4卤代烷基和C1-C4烷氧基；或A-Q可以一起是C1-C10烷基，其可以被1或2个取代基所取代，所述取代基选自═O、OH、C1-C4烷氧基、C1-C4烷基硫基、卤素或C1-C4烷基羰基氧基；X是C═O、C═S或SO2；Ar是选自苯基、萘基、吡啶基、嘧啶基、呋喃基和噻吩基的选用性取代芳基；R1到R6和R9如权利要求和说明书中所述。
• Small Molecule Fluorescent Ligands for the Atypical Chemokine Receptor 3 (ACKR3)
  作者：Sebastian Dekkers、Dehan Comez、Noemi Karsai、Marta Arimont-Segura、Meritxell Canals、Birgit Caspar、Chris de Graaf、Laura E. Kilpatrick、Rob Leurs、Barrie Kellam、Stephen J. Hill、Stephen J. Briddon、Michael J. Stocks

  DOI：10.1021/acsmedchemlett.3c00469

  日期：2024.1.11

  atypical chemokine receptor 3 (ACKR3) is a receptor that induces cancer progression and metastasis in multiple cell types. Therefore, new chemical tools are required to study the role of ACKR3 in cancer and other diseases. In this study, fluorescent probes, based on a series of small molecule ACKR3 agonists, were synthesized. Three fluorescent probes, which showed specific binding to ACKR3 through a

  非典型趋化因子受体 3 （ACKR3） 是一种在多种细胞类型中诱导癌症进展和转移的受体。因此，需要新的化学工具来研究 ACKR3 在癌症和其他疾病中的作用。在这项研究中，基于一系列小分子 ACKR3 激动剂合成了荧光探针。公开了三种荧光探针，它们通过基于发光的 NanoBRET 结合测定 （pKd 范围为 6.8 至 7.8） 显示与 ACKR3 的特异性结合。由于它们对 ACKR3 的高亲和力，我们已经在竞争结合实验和共聚焦显微镜研究中展示了它们的应用，显示了该受体的细胞分布。
• Pharmacological Characterization and Radiolabeling of VUF15485, a High-Affinity Small-Molecule Agonist for the Atypical Chemokine Receptor ACKR3
  作者：Aurelien M. Zarca、Ilze Adlere、Cristina P. Viciano、Marta Arimont-Segura、Max Meyrath、Icaro A. Simon、Jan Paul Bebelman、Dennis Laan、Hans G. J. Custers、Elwin Janssen、Kobus L. Versteegh、Maurice C. M. L. Buzink、Desislava N. Nesheva、Reggie Bosma、Iwan J. P. de Esch、Henry F. Vischer、Maikel Wijtmans、Martyna Szpakowska、Andy Chevigné、Carsten Hoffmann、Chris de Graaf、Barbara A. Zarzycka、Albert D. Windhorst、Martine J. Smit、Rob Leurs

  DOI：10.1124/molpharm.123.000835

  日期：2024.4

  (Kd = 8.2 nM). Additionally, [3H]VUF15485 shows rapid binding kinetics and consequently a short residence time (<2 minutes) for binding to ACKR3. The selectivity of [3H]VUF15485 for ACKR3, was confirmed by binding studies, whereupon CXCR3, CXCR4, and ACKR3 small-molecule ligands were competed for binding against the radiolabeled agonist. Interestingly, the chemokine ligands CXCL11 and CXCL12 are not able

  非典型趋化因子受体 3 (ACKR3)，以前称为 CXCR7，被认为是一个有趣的药物靶点。在这项研究中，我们报告了 VUF15485（一种新型 ACKR3 小分子激动剂）的合成、药理学表征和放射性标记，它将作为研究这种β-抑制蛋白偏向趋化因子受体的重要新工具。根据 [ 125 I]CXCL12 竞争结合实验的测量，VUF15485 以纳摩尔亲和力 (pIC 50 = 8.3) 与人 ACKR3 结合。此外，在基于生物发光共振能量转移的β -arrestin2 招募测定中，VUF15485 充当有效的 ACKR3 激动剂 (pEC 50 = 7.6)，并且当使用新开发的荧光共振能量转移时，与 CXCL12 相比，显示出相似的受体激活程度。基于ACKR3构象传感器。此外，针对（非典型）趋化因子受体组（激动剂和拮抗剂模式）测试的 ACKR3 激动剂 VUF15485 被证明对 ACKR3 具有选择性。
• Dehydrogenative β-Arylation of Saturated Aldehydes Using Transient Directing Groups
  作者：Xing-Long Zhang、Gao-Fei Pan、Xue-Qing Zhu、Rui-Li Guo、Ya-Ru Gao、Yong-Qiang Wang

  DOI：10.1021/acs.orglett.9b00695

  日期：2019.4.19

  An unprecedented cross-dehydrogenative-coupling (CDC) reaction of saturated aldehyde beta-C-H with arenes to form cinnamaldehydes via the cleavages of four C-H bonds has been developed. The reaction possesses complete E-stereoselectivity for the C = C double bond. The protocol is featured by atom and step economy, mild reaction conditions, and convenient operation.
• HYDRAZIDE COMPOUNDS FOR COMBATING ANIMAL PESTS
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP1819224A1

  公开（公告）日：2007-08-22