(E)-3-(3-fluorophenyl)-2-methylacrylaldehyde | 1375800-38-6

• 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-(3-fluorophenyl)-2-methylacrylaldehyde
• 英文别名: 3-(3-Fluorophenyl)-2-methylacrylaldehyde；(E)-3-(3-fluorophenyl)-2-methylprop-2-enal
• CAS: 1375800-38-6
• 化学式: C₁₀H₉FO
• 分子量: 164.179
• InChiKey: BKRVIAAGTQOUAO-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-fluorophenyl)-2-methylacrylaldehyde 在 sodium tetrahydroborate 、 magnesium sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 121.17h， 生成 (E)-3-(3-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：

  (E)-3-(3-fluorophenyl)-2-methylprop-2-en-1-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (E)-3-(3-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

• S_N2″-Selective and Enantioselective Substitution with Unsaturated Organoboron Compounds and Catalyzed by a Sulfonate-Containing NHC-Cu Complex
  作者：Yuebiao Zhou、Ying Shi、Sebastian Torker、Amir H. Hoveyda

  DOI：10.1021/jacs.8b10885

  日期：2018.12.5

  53-89% yield, 69-96% SN2″ selectivity, 98:2 to >98:2 E: Z ratio, and 94:6-98:2 er. Insight regarding several of the unique mechanistic attributes of the catalytic process was obtained on the basis of kinetic isotope effect measurements and DFT studies. These investigations indicate that cationic π-allyl-Cu complexes are likely intermediates, clarifying the role of the s-cis and s-trans conformers of

  公开了第一个广泛适用的 SN2" 选择性和对映选择性催化取代策略。转化由 5.0 mol% 的含磺酸盐的 NHC-Cu 复合物（NHC = N-杂环卡宾）促进，并在市售的烯基-B（pin）（pin = pinacolato）或易于获得的甲硅烷基保护的炔丙基-B(pin)。发现无环、或芳基-、杂芳基-和烷基取代的五-2,4-二烯基磷酸酯，以及仅带有1,2-二取代烯烃或1,2-二取代和三取代烯烃的那些是合适的起始材料。环状磷酸二烯酯也可用作底物。以 51-82% 的收率获得了除 1,3-二烯基外还含有易于官能化的炔丙基部分（来自与丙二烯基-B(pin) 的反应）的产物，84-97% SN2" 选择性，89:11-97:3 E: Z 比和 86:14-98:2 对映体比 (er)。与甲硅烷基保护的炔丙基-B(pin) 化合物反应导致形成相应的甲硅烷基-烯丙基产物，产率 53-89%，SN2" 选择性
• 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。
• HYDRAZIDE COMPOUNDS FOR COMBATING ANIMAL PESTS
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP1819224A1

  公开（公告）日：2007-08-22
• [EN] HYDRAZIDE COMPOUNDS FOR COMBATING ANIMAL PESTS<br/>[FR] COMPOSES D'HYDRAZIDE POUR LUTTER CONTRE DES PARASITES ANIMAUX
  申请人：BASF AG

  公开号：WO2006058730A1

  公开（公告）日：2006-06-08

  [EN] 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, C₁-C₄ alkylidene, O-C₁-C₄ alkylidene, S-C₁-C₄ alkylidene and NR⁹-C₁-C₄ 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, C₁-C₄ haloalkyl and C₁-C₄ alkoxy; or A-Q may together be C₁-C₁₀-alkyl, which may be substituted by 1 or 2 substituents selected from the group consisting of =O, OH, C₁-C₄-alkoxy, C₁-C₄-alkylthio, halogen or C₁-C₄-alkylcarbonyloxy, X is C=O, C=S or SO₂; Ar is an optionally substituted aromatic radical selected from phenyl, naphthyl, pyridyl, pyrimidyl, furyl and thienyl; and R¹ to R⁶ and R⁹ are as described in the claims and the specification.
  [FR] La présente invention concerne de nouveaux composés d'hydrazide pouvant être employés dans la lutte contre des parasites animaux, notamment des insectes, des arachnides et des nématodes, ainsi que les sels desdits composés. La présente invention concerne également une méthode de lutte contre les insectes, les nématodes et les arachnides. Les composés d'hydrazide selon l'invention sont décrits par la formule générale (I) où .. représente un vide ou une liaison covalente; A est un radical cyclique éventuellement substitué sélectionné parmi les phényles, les naphtyles et un radical hétérocyclique à 5 ou 6 chaînons comprenant entre 1 et 4 hétéroatomes sélectionnés parmi O, N et S, ces hétéroatomes pouvant être différents les uns des autres, ledit radical hétérocyclique pouvant comprendre un groupement carbonyle comme chaînon cyclique; Q représente une liaison simple, un alkylidène en C₁-C₄, un alkylidène en O-C₁-C₄, un alkylidène en S-C₁-C₄ ou un alkylidène en NR⁹-C₁-C₄, ledit groupement alkylidène au sein des quatre radicaux précédents pouvant comporter entre 0 et 4 substituants sélectionnés parmi OH, =O, les halogènes, les halogénoalkyles en C₁-C₄ et les alcoxy en C₁-C₄; A-Q peuvent représenter conjointement un groupement alkyle en C₁-C₁₀, éventuellement substitué par 1 ou 2 substituants sélectionnés au sein du groupe constitué par =O, OH, les alcoxy en C₁-C₄, les alkylthio en C₁-C₄, les halogènes et les alkylcarbonyloxy en C₁-C₄, X représente C=O, C=S ou SO₂; Ar est un radical aromatique éventuellement substitué sélectionné parmi les phényles, les naphtyles, les pyridyles, les pyrimidyles, les furyles et les thiényles; et R¹ à R⁶ et R⁹ sont tels que décrits dans les revendications et la description.
• Synthesis, modeling and functional activity of substituted styrene-amides as small-molecule CXCR7 agonists
  作者：Maikel Wijtmans、David Maussang、Francesco Sirci、Danny J. Scholten、Meritxell Canals、Azra Mujić-Delić、Milagros Chong、Kristell L.S. Chatalic、Hans Custers、Elwin Janssen、Chris de Graaf、Martine J. Smit、Iwan J.P. de Esch、Rob Leurs

  DOI：10.1016/j.ejmech.2012.02.041

  日期：2012.5

  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.