methyl 2-(naphthalen-2-yloxy)propanoate | 30406-75-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-(naphthalen-2-yloxy)propanoate
• 英文别名: 2-(2-Naphthoxy)propionic acid methyl ester；methyl 2-naphthalen-2-yloxypropanoate
• CAS: 30406-75-8
• 化学式: C₁₄H₁₄O₃
• mdl: MFCD03130014
• 分子量: 230.263
• InChiKey: XPUKIATWMAOOFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(naphthalen-2-yloxy)propanoate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以17.56 g的产率得到2-(2-naphthoxy)propanol
  参考文献：
  名称：

  A highly active ionic liquid catalyst for Morita–Baylis–Hillman reaction

  摘要：

  The Morita-Baylis-Hillman reaction is an efficient carbon-carbon bond forming reaction for the preparation of alpha-methylene-beta-hydroxycarbonyl compounds. A new and highly active di-naphthalene imidazolium salt has been synthesized. We have found that 1, 3-bis[2-(naphthalene-2-yloxy)propyl]imidazolium bromid promoted the Morita-Baylis-Hillman reaction of various aryl aldehyde compounds in the absence of solvents. Our studies show that the Morita-Baylis-Hillman reaction by the influence of ionic liquid to give a high yield and short reaction time. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.048
• 作为产物：
  描述：

  2-(2-萘氧基)丙酸 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 methyl 2-(naphthalen-2-yloxy)propanoate
  参考文献：
  名称：

  Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates

  摘要：

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.009

文献信息

• Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon–Carbon Bonds with Chlorine on Demand
  作者：Feng Liu、Na Wu、Xu Cheng

  DOI：10.1021/acs.orglett.1c00704

  日期：2021.4.16

  electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.

  用氯进行氯化是直接的，高反应性的，并且用途广泛，但是有很大的局限性。在这封信中，我们介绍了一种可以结合电化学转化效率和氯的高反应活性的方案。通过使用Cl 3 CCN作为氯化物源，最多提供三个氯原子，该反应可按需就地生成和消耗氯，以实现芳族化合物和电有效链烯烃的氯化。
• An exit beyond the pharmacophore model for 5-HT6R agents - a new strategy to gain dual 5-HT6/5-HT2A action for triazine derivatives with procognitive potential
  作者：Katarzyna Kucwaj-Brysz、Wesam Ali、Rafał Kurczab、Sylwia Sudoł-Tałaj、Natalia Wilczyńska-Zawal、Magdalena Jastrzębska-Więsek、Grzegorz Satała、Barbara Mordyl、Ewa Żesławska、Agnieszka-Olejarz-Maciej、Kinga Czarnota、Gniewomir Latacz、Anna Partyka、Anna Wesołowska、Wojciech Nitek、Jadwiga Handzlik

  DOI：10.1016/j.bioorg.2022.105695

  日期：2022.4

  receptor (5-HT6/5-HT2AR) dual antagonists in a group of 1,3,5-triazine compounds as a result of an exit beyond the hydrophobic feature of the pharmacophore model for 5-HT6R antagonists. Design and synthesis of the series (2–16) of new O- and S-containing ether derivatives of 1,3,5-triazines with the double-ring aromatic region have been performed. The new compounds were examined within the comprehensive pharmacological

  这项研究使我们能够在一组 1,3,5-三嗪化合物中找到第一个高效的 5-HT 6 /5-HT 2A受体（5-HT 6 /5-HT 2A R）双重拮抗剂，因为5-HT 6 R 拮抗剂药效团模型的疏水特征之外的出口。已经进行了具有双环芳族区域的 1,3,5-三嗪的新的含 O 和 S 醚衍生物系列 ( 2 – 16 ) 的设计和合成。在综合药理学筛选中检查了新化合物，包括：放射性配体结合测定、体外功能和 ADMET 研究以及大鼠的行为测试。还分析了晶体学方面和计算机辅助的构效关系。综合方法导致选择化合物12 (4-(4-methylpiperazin-1-yl)-6-(2-(naphthalen-2-ylthio)propan-2-yl)-1,3,5-triazin-2 -胺）具有最显着的双重 5-HT 6 /5-HT 2A R 拮抗作用（5-HT 6 R K i  = 11 nM，5-HT 2A
• JPS5513203A
  申请人：——

  公开号：JPS5513203A

  公开（公告）日：1980-01-30
• US4840663A
  申请人：——

  公开号：US4840663A

  公开（公告）日：1989-06-20
• US5217525A
  申请人：——

  公开号：US5217525A

  公开（公告）日：1993-06-08