2-hydroxy-3-(prop-1-enyl)benzaldehyde | 206752-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-3-(prop-1-enyl)benzaldehyde
• 英文别名: 2-Hydroxy-3-propenyl-benzaldehyd；2-Hydroxy-3-prop-1-enylbenzaldehyde
• CAS: 206752-65-0
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: FERLVEKCFKGWOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-(prop-1-enyl)benzaldehyde 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.0h， 生成 2H-chromene-8-carbaldehyde
  参考文献：
  名称：

  Ring-closing metathesis for the synthesis of 2H- and 4H-chromenes

  摘要：

  Six 4H-chromenes were synthesized from substituted phenols using vinylstannylation and ring-closing metathesis (RCM) as key steps. In addition, a different approach involving amongst other steps, an aryl allyl isomerization and RCM afforded a set of seven 2H-chromenes from phenolic precursors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.020
• 作为产物：
  描述：

  3-烯丙基-2-羟基苯甲醛 在 [RuHCl(CO)(PPh₃)₃] 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以89%的产率得到2-hydroxy-3-(prop-1-enyl)benzaldehyde
  参考文献：
  名称：

  Ring-closing metathesis for the synthesis of 2H- and 4H-chromenes

  摘要：

  Six 4H-chromenes were synthesized from substituted phenols using vinylstannylation and ring-closing metathesis (RCM) as key steps. In addition, a different approach involving amongst other steps, an aryl allyl isomerization and RCM afforded a set of seven 2H-chromenes from phenolic precursors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.020

文献信息

• Synthesis, crystal structure and biological evaluation of three new Rh(III) complexes incorporating benzimidazole derivatives
  作者：Jun-Hong Liu、Feng-Hua Pan、Zhen-Feng Wang、Rong Wang、Lin Yang、Qi-Pin Qin、Ming-Xiong Tan

  DOI：10.1016/j.inoche.2020.108017

  日期：2020.8

  Abstract Three new non-cisplatin analogs [Rh(BID1)(CH3OH)]⋅CH3OH (Rh-1), [Rh(BID2)(CH3OH)]⋅CH3OH (Rh-2) and [Rh(BID3)(CH3OH)]⋅2CH3OH (Rh-3) bearing benzimidazole derivatives (BID1−BID-3) were first prepared as potential anti-tumor compounds. The Rh-3 complex with 8-fluoro group in BID-3 ligand exhibited potential antiproliferative activity against multidrug-resistant human lung adenocarcinoma A549/DDP

  摘要 三种新的非顺铂类似物 [Rh(BID1)(CH3OH)]⋅CH3OH (Rh-1)、[Rh(BID2)(CH3OH)]⋅CH3OH (Rh-2) 和 [Rh(BID3)(CH3OH)]带有苯并咪唑衍生物（BID1-BID-3）的2CH3OH（Rh-3）首先被制备为潜在的抗肿瘤化合物。BID-3配体中含有8-氟基团的Rh-3复合物对多药耐药人肺腺癌A549/DDP和顺铂耐药人卵巢癌SK-OV-3/DDP细胞表现出潜在的抗增殖活性，最多提高5.0倍在相同条件下比 Rh-1、Rh-2 和顺铂更有效。重要的是，与人正常肝脏 HL-7702 细胞相比，Rh-1-Rh-3 对 A549/DDP 细胞更具选择性。Rh-2和Rh-3引起线粒体功能障碍的顺序如下：Rh-3>Rh-2。