MON8 | 1031269-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: MON8
• 英文别名: monesin 1-naphthylmethyl ester
• CAS: 1031269-33-6
• 化学式: C₄₇H₇₀O₁₁
• 分子量: 811.066
• InChiKey: JEBSBTJTEMCJSP-REWYTJJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  58.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  142.37
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  MON8 、 lithium perchlorate 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Structure of 1-naphthylmethyl ester of monensin A complexes with monovalent metal cations

  摘要：

  A new 1-naphthylmethyl ester of monensin A (MON8) has been synthesized and its capability of complex formation with Li+, Na+ and K+ cations has been studied by mass spectrometry, spectroscopic and PM5 semiempirical methods. ESI mass spectrometry indicates that MON8 forms complexes of exclusively 1:1 stoichiometry with these cations. The fragmentation pathways of MON8 complexes are discussed. The FT-IR spectra of MON8 complexes with Li+ and Na+ cations indicate an equilibrium between two complex structures, in which the carbonyl ester group is either involved or not involved in the complexation process, whereby the equilibrium is shifted towards the latter structure. The structures of the MON8 complexes with Li+, Na+ and K+ cations are stabilized by intramolecular hydrogen bonds in which the OH groups are always involved. The structures are visualized using PM5 semiempirical method and discussed in detail. We show that MON8-Na+ complex has a pseudo-crown ring structure which increases the affinity of MON8 to this cation. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2008.11.046
• 作为产物：
  描述：

  monensin A sodium salt 、 (氯甲基)萘 在 硫酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 5.0h， 以272 mg的产率得到MON8
  参考文献：
  名称：

  Structure of 1-naphthylmethyl ester of monensin A complexes with monovalent metal cations

  摘要：

  A new 1-naphthylmethyl ester of monensin A (MON8) has been synthesized and its capability of complex formation with Li+, Na+ and K+ cations has been studied by mass spectrometry, spectroscopic and PM5 semiempirical methods. ESI mass spectrometry indicates that MON8 forms complexes of exclusively 1:1 stoichiometry with these cations. The fragmentation pathways of MON8 complexes are discussed. The FT-IR spectra of MON8 complexes with Li+ and Na+ cations indicate an equilibrium between two complex structures, in which the carbonyl ester group is either involved or not involved in the complexation process, whereby the equilibrium is shifted towards the latter structure. The structures of the MON8 complexes with Li+, Na+ and K+ cations are stabilized by intramolecular hydrogen bonds in which the OH groups are always involved. The structures are visualized using PM5 semiempirical method and discussed in detail. We show that MON8-Na+ complex has a pseudo-crown ring structure which increases the affinity of MON8 to this cation. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2008.11.046

文献信息

• Synthesis and antimicrobial properties of Monensin A esters
  作者：Adam Huczyński、Joanna Stefańska、Piotr Przybylski、Bogumil Brzezinski、Franz Bartl

  DOI：10.1016/j.bmcl.2008.03.038

  日期：2008.4

  The esters (2-10) of the ionophore antibiotic Monensin (1) were synthesized by four different methods, which are discussed in detail. These new esters were characterized by various spectroscopic techniques and subsequently tested in the face of their antimicrobial properties. Three derivatives (3, 8 and 10) showed activity against Gram-positive bacteria. Additionally derivative (10) exhibited a relatively low antifungal activity against Candida in contrast to Monensin A. (c) 2008 Elsevier Ltd. All rights reserved.