3-(cinnamyloxy)benzaldehyde | 192457-33-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(cinnamyloxy)benzaldehyde
• 英文别名: 3-(3-Phenylprop-2-enoxy)benzaldehyde
• CAS: 192457-33-3
• 化学式: C₁₆H₁₄O₂
• mdl: MFCD06760257
• 分子量: 238.286
• InChiKey: HVDDIFSUJMSXNM-UHFFFAOYSA-N

物化性质

• 沸点：
  415.9±33.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3-(cinnamyloxy)benzaldehyde 在 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3-(cinnamyloxy)phenyl)(cyclopentyl)methanone
  参考文献：
  名称：

  通过CH键活化的铱催化烯烃的对映选择性氢芳基化：实验和计算。

  摘要：

  开发了一种新的未活化烯烃的催化对映选择性加氢芳基化反应，可快速获得官能化的手性二氢苯并呋喃，收率高，对映选择性优异。简单的芳族酮或酰胺充当引导基团，允许在更受阻的邻位进行区域选择性反应。叔苄基立体中心是在温和的反应条件下直接获得的，并且完全经济地从容易获得的起始原料中获得。

  DOI：

  10.1002/chem.202001793
• 作为产物：
  描述：

  3-苄氧基苯甲醛 、 间羟基苯甲醛 、 肉桂基氯 以79%的产率得到3-(cinnamyloxy)benzaldehyde
  参考文献：
  名称：

  Design and synthesis of l- and d-phenylalanine derived rhodanines with novel C5-arylidenes as inhibitors of HCV NS5B polymerase

  摘要：

  Hepatitis C virus (HCV) NS5B polymerase is a key target for anti-HCV therapeutics development. Herein, we report the synthesis and in vitro evaluation of anti-NS5B polymerase activity of a molecular hybrid of our previously reported lead compounds 1 (IC50 = 7.7 mu M) and 2 (IC50 = 10.6 mu M) as represented by hybrid compound 27 (IC50 = 6.7 mu M). We have explored the optimal substituents on the terminal phenyl ring of the 3-phenoxybenzylidene moiety in 27, by generating a set of six analogs. This resulted in the identification of compound 34 with an IC50 of 2.6 mu M. To probe the role of stereochemistry towards the observed biological activity, we synthesized and evaluated the D-isomers 41 (IC50 = 19.3 mu M) and 45 (IC50 = 5.4 mu M) as enantiomers of the L-isomers 27 and 34, respectively. The binding site of compounds 32 and 34 was mapped to palm pocket-I (PP-I) of NS5B. The docking models of 34 and 45 within the PP-I of NS5B were investigated to envisage the molecular mechanism of inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.041

文献信息

• 一种新型手性二氢苯并呋喃酰胺的合成方法及其应用
  申请人：皖南医学院第一附属医院（皖南医学院弋矶山医院）

  公开号：CN117624095A

  公开（公告）日：2024-03-01

  本发明公开了一种新型手性二氢苯并呋喃酰胺的合成方法及其应用，其化合物的结构式为(I)：#imgabs0#其中，R1、R2、R3、R4、R5各自独立为H、F、Cl、Br、OCH3、芳香类取代基、C1‑C5的直链或者支链烷基中的一种。本发明所制备的手性二氢苯并呋喃‑3‑烷基‑4‑甲酰基‑5‑酰胺化合物可通过改变R1‑R5修饰衍生其结构，可能调控其生物活性。进一步对该化合物进行生物体内的实验发现，该化合物具有良好的镇静作用，使得其在生物医学等领域具有重要的应用前景。
• The synthesis and SAR study of phenylalanine-derived (Z)-5-arylmethylidene rhodanines as anti-methicillin-resistant Staphylococcus aureus (MRSA) compounds
  作者：Bhargav A. Patel、Charles R. Ashby、Diane Hardej、Tanaji T. Talele

  DOI：10.1016/j.bmcl.2013.08.059

  日期：2013.10

  A focused library of rhodanine compounds containing novel substituents at the C5-position was synthesized and tested in vitro against a panel of clinically relevant MRSA strains. The present SAR study was based on our lead compound 1 (MIC = 1.95 mu g/mL), with a focus on identifying optimal C5-arylidene substituents. In order to obtain this objective, we condensed several unique aromatic aldehydes with phenylalanine-derived rhodanine intermediates to obtain C5-substituted target rhodanine compounds for evaluation as anti-MRSA compounds. These efforts produced three compounds with significant efficacy: 23, 32 and 44, with MIC values ranging from 0.98 to 1.95 mu g/mL against all tested MRSA strains as compared to the reference antibiotics penicillin G (MIC = 15.60-250.0 mu g/mL) and ciprofloxacin (MIC = 7.80-62.50 mu g/mL) and comparable to that of vancomycin (MIC = 0.48 mu g/mL). In addition, compounds 24, 28, 37, 41, 46 and 48 (MIC = 1.95-3.90 mu g/mL) were efficacious against all MRSA strains. The majority of the synthesized compounds had bactericidal activity at concentrations only two to fourfold higher than their MIC. Overall, the results suggest that compounds 23, 32 and 44 may be of potential use in the treatment of MRSA infections. (C) 2013 Elsevier Ltd. All rights reserved.
• Design and synthesis of l- and d-phenylalanine derived rhodanines with novel C5-arylidenes as inhibitors of HCV NS5B polymerase
  作者：Bhargav A. Patel、Ramalingam Krishnan、Nikhil Khadtare、K.R. Gurukumar、Amartya Basu、Payal Arora、Aaditya Bhatt、Maulik R. Patel、Dibyendu Dana、Sanjai Kumar、Neerja Kaushik-Basu、Tanaji T. Talele

  DOI：10.1016/j.bmc.2013.03.041

  日期：2013.6

  Hepatitis C virus (HCV) NS5B polymerase is a key target for anti-HCV therapeutics development. Herein, we report the synthesis and in vitro evaluation of anti-NS5B polymerase activity of a molecular hybrid of our previously reported lead compounds 1 (IC50 = 7.7 mu M) and 2 (IC50 = 10.6 mu M) as represented by hybrid compound 27 (IC50 = 6.7 mu M). We have explored the optimal substituents on the terminal phenyl ring of the 3-phenoxybenzylidene moiety in 27, by generating a set of six analogs. This resulted in the identification of compound 34 with an IC50 of 2.6 mu M. To probe the role of stereochemistry towards the observed biological activity, we synthesized and evaluated the D-isomers 41 (IC50 = 19.3 mu M) and 45 (IC50 = 5.4 mu M) as enantiomers of the L-isomers 27 and 34, respectively. The binding site of compounds 32 and 34 was mapped to palm pocket-I (PP-I) of NS5B. The docking models of 34 and 45 within the PP-I of NS5B were investigated to envisage the molecular mechanism of inhibition. (C) 2013 Elsevier Ltd. All rights reserved.
• Iridium‐Catalyzed Enantioselective Hydroarylation of Alkenes through C−H bond Activation: Experiment and Computation
  作者：Valmik S. Shinde、Manoj V. Mane、Luigi Cavallo、Magnus Rueping

  DOI：10.1002/chem.202001793

  日期：2020.7.2

  A new catalytic enantioselective hydroarylation of unactivated olefins is developed that provides rapid access to functionalized chiral dihydrobenzofurans with good yields and excellent enantioselectivities. Simple aromatic ketones or amides act as a directing group allowing the regioselective reaction at the more hindered ortho position. Tertiary benzylic stereocenters are obtained directly under

  开发了一种新的未活化烯烃的催化对映选择性加氢芳基化反应，可快速获得官能化的手性二氢苯并呋喃，收率高，对映选择性优异。简单的芳族酮或酰胺充当引导基团，允许在更受阻的邻位进行区域选择性反应。叔苄基立体中心是在温和的反应条件下直接获得的，并且完全经济地从容易获得的起始原料中获得。