chloromethyl 2-naphthoate | 49598-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: chloromethyl 2-naphthoate
• 英文别名: Chloromethyl naphthalene-2-carboxylate；chloromethyl naphthalene-2-carboxylate
• CAS: 49598-76-7
• 化学式: C₁₂H₉ClO₂
• 分子量: 220.655
• InChiKey: VEPKRNCULSKWAV-UHFFFAOYSA-N

物化性质

• 沸点：
  372.0±25.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  chloromethyl 2-naphthoate 在 Amberlite IRA-400 Cl(-) exchange resin 、 sodium iodide 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 2-<(hydroxyimino)methyl>-3-methyl-2-<(2'-naphthoyloxy)methyl>imidazolium chloride
  参考文献：
  名称：

  Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 2. Preparation and in vitro and in vivo evaluaton of 1-(alkoxymethyl)-2-[(hydroxyimino)methyl]-3-methylimidazolium halides for reactivation of organophosphorus-inhibited acetylcholinesterases

  摘要：

  A series of structurally related mono- and bis-1,3-disubstituted 2-[(hydroxyimino)methyl]imidazolium halides were evaluated in vitro for their ability to reactivate electric eel, bovine, and human erythrocyte (RBC) acetylcholinesterases (AChE) inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP) and 3,3-dimethyl-2-butyl methyl-phosphonofluoridate (soman, GD). All new compounds were characterized for (hydroxyimino)methyl acid dissociation constant, nucleophilicity, octanol-buffer partition coefficient, reversible AChE inhibition, and kinetics of reactivation of EPMP-inhibited AChEs. For GD-inhibited AChEs, maximal reactivation was used to compare compounds since rapid phosphonyl enzyme dealkylation "aging" complicated interpretation of kinetic constants. For comparison, we also evaluated three known pyridinium therapeutics, 2-PAM, HI-6, and toxogonin. In vivo evaluation in mice revealed that when selected imidazolium compounds were coadministered with atropine sulfate, they were effective in providing lifesaving protection against both GD and EPMP challenges. This was a major accomplishment in the search for effective anticholinesterase therapeutics--the synthesis and preliminary evaluation of the first new monoquaternary soman antidotes with potencies superior to 2-PAM. Significantly, there was an apparent inverse relationship between in vitro and in vivo results; the most potent in vivo compounds proved to be the poorest in vitro reactivators. These results suggested that an alternative and possibly novel antidotal mechanism of protective action may be applicable for the imidazolium aldoximes. Selected compounds were also evaluated for their inhibition of AChE phosphorylation by GD and antimuscarinic and antinicotinic receptor blocking effects.

  DOI：

  10.1021/jm00122a034
• 作为产物：
  描述：

  二氯甲烷 、 2-萘甲醛 在 叔丁基过氧化氢 、 sodium azide 、 四丁基碘化铵 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以79%的产率得到chloromethyl 2-naphthoate
  参考文献：
  名称：

  一种羧酸酯类化合物的合成方法

  摘要：

  本发明提供一种如式(1)、式(2)或式(3)所示的酯类化合物的合成方法，所述方法为：将醛类化合物、叠氮化钠、四丁基碘化铵和卤代化合物溶于溶剂中，或将醛类化合物、叠氮化钠、四丁基碘化铵直接溶于卤代化合物中，在90‑100℃下反应1～12h，反应结束后，反应液经后处理得到式(1)所示的化合物。本发明反应条件温和，无需强酸强碱以及金属参与，合成方法简单高效、产率高、底物适用范围广且具有放大生产的潜力，具有较大的潜在经济价值。

  公开号：

  CN106588644B

文献信息

• [EN] RODENTICIDAL NORBORMIDE ANALOGUES<br/>[FR] ANALOGUES DE NORBORMIDE RODENTICIDE
  申请人：LANDCARE RES NEW ZEALAND LTD

  公开号：WO2013133726A1

  公开（公告）日：2013-09-12

  The present invention relates to norbormide analogues having rodenticidal activity; rodenticidal compositions comprising the analogues; uses of the analogues as rodenticides; uses of the analogues in the manufacture of rodenticidal compositions; and methods for controlling rodents using the compositions.

  本发明涉及具有杀鼠活性的诺波酰胺类似物；包括这些类似物的杀鼠组合物；将这些类似物用作杀鼠剂的用途；将这些类似物用于制造杀鼠组合物的用途；以及使用这些组合物控制啮齿动物的方法。
• Design and synthesis of prodrugs of the rat selective toxicant norbormide
  作者：David Rennison、Olivia Laita、Sergio Bova、Maurizio Cavalli、Brian Hopkins、Darwin S. Linthicum、Margaret A. Brimble

  DOI：10.1016/j.bmc.2012.05.014

  日期：2012.7

  Norbormide [5-(α-hydroxy-α-2-pyridylbenzyl)-7-(α-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide] (NRB), an existing but infrequently used rodenticide, is known to be uniquely toxic to rats but relatively harmless to other rodents and mammals. However, one major drawback of NRB as a viable rodenticide relates to an evolutionary aversion developed by the rat leading to sub-lethal dosing due to

  已知存在但很少使用的杀虫剂降冰片[5-（α-羟基-α-2-吡啶基苄基）-7-（α-2-吡啶基苄基）-5-降冰片烯-2,3-二甲酰亚胺]（NRB）对大鼠有独特的毒性，但对其他啮齿动物和哺乳动物则无害。然而，作为一种有效的灭鼠剂，NRB的一个主要缺点与大鼠产生的进化厌恶有关，这是由于其令人不快的“味觉”或起效迅速而导致亚致死剂量的。为了“掩盖”这种急性反应，准备了一系列NRB前药。描述了它们的合成和生物学评估（体外血管收缩活性，体外水解和酶稳定性以及体内致死性/适口性）。化合物19 在症状发作方面表现出最有前途的表现，随后被证明对大鼠而言更可口。
• Enantioselective Synthesis of Biaryl Atropisomers via Pd/Norbornene-Catalyzed Three-Component Cross-Couplings
  作者：Linlin Ding、Xianwei Sui、Zhenhua Gu

  DOI：10.1021/acscatal.8b01037

  日期：2018.6.1

  Three-component cross-coupling cocatalyzed by palladium and norbornene is reported for the synthesis of biaryl atropisomers. This domino reaction gave optimal yield and enantioselectivity with a P,C-type ligand bearing axial chirality and P chiral center. The process showed advantages over traditional cross-coupling because of its step economy and its compatibility with readily available ortho-substituted

  据报道，钯和降冰片烯共催化的三组分交叉偶联用于联芳基阻转异构体的合成。与具有轴向手性和P手性中心的P，C型配体一起，该多米诺反应产生了最佳的收率和对映选择性。该方法显示出优于传统的交叉偶联的优点，因为它的步骤经济性以及与容易获得的邻取代的芳基卤化物的相容性，因此可以代替连续的三取代的芳基卤化物使用邻位取代的芳基卤化物。
• RODENTICIDAL NORBORMIDE ANALOGUES
  申请人：Landcare Research New Zealand Limited

  公开号：US20150025113A1

  公开（公告）日：2015-01-22

  The present invention relates to norbormide analogues having rodenticidal activity; rodenticidal compositions comprising the analogues; uses of the analogues as rodenticides; uses of the analogues in the manufacture of rodenticidal compositions; and methods for controlling rodents using the compositions.

  本发明涉及具有杀鼠活性的诺博酰胺类似物；包含该类似物的杀鼠组合物；将该类似物用作杀鼠剂的用途；将该类似物用于制造杀鼠组合物的用途；以及使用该组合物控制啮齿动物的方法。
• Rodenticidal norbormide analogues
  申请人：Landcare Research New Zealand Limited

  公开号：US09198420B2

  公开（公告）日：2015-12-01

  The present invention relates to norbormide analogs having rodenticidal activity; rodenticidal compositions comprising the analogs; uses of the analogs as rodenticides; uses of the analogs in the manufacture of rodenticidal compositions; and methods for controlling rodents using the compositions.

  本发明涉及具有杀鼠活性的诺博酰胺类似物；包含该类似物的杀鼠组合物；将该类似物用作杀鼠剂的用途；将该类似物用于制造杀鼠组合物的用途；以及使用该组合物控制啮齿动物的方法。