m-Methoxythiobenzoesaeure-O-methylester | 28145-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: m-Methoxythiobenzoesaeure-O-methylester
• 英文别名: O-methyl 3-methoxybenzothioate；O-methyl 3-methoxythiobenzoate；O-methyl 3-methoxybenzenecarbothioate
• CAS: 28145-40-6
• 化学式: C₉H₁₀O₂S
• 分子量: 182.243
• InChiKey: VTAZHYXWKUQCFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  m-Methoxythiobenzoesaeure-O-methylester 在 氘代吡啶 、 氧气 、 tetraphenylporphyrin 作用下， 以 1-萘乙酮 、 氘代氯仿 为溶剂， 反应 2.0h， 生成 3-甲氧基苯甲酸甲酯
  参考文献：
  名称：

  Fenchyl取代的1,2-二氧杂环丁烷可替代金刚烷基衍生物用于生物分析

  摘要：

  报道了含螺甲醚基取代基的1,2-二氧杂环丁烷的化学发光参数和热稳定性的合成和研究。通过相应的烯烃的光氧合反应合成了三个芬基取代的1,2-二氧杂环丁烷，这些烯烃是通过易得的（-）-芬酮的巴顿-凯洛格烯化反应制得的。芬基取代的1,2-二氧杂环丁烷显示出与相应的螺金刚烷基取代的衍生物相似的热稳定性，尽管在单分子分解方面比后一种衍生物稍不稳定，后者在多种化学发光中被广泛用作标记免疫测定。氟化物诱导的一种可触发的1,1,2-二氟苯醚衍生物的分解显示出与相应的金刚烷基取代的衍生物相似的动力学参数。在1％范围内的化学发光量子产率也与其他广泛使用的化学发光系统的鲁米诺反应相似。这些结果表明，在生物分析应用中，芬基取代的1，2-二氧杂环丁烷可以潜在地用作便宜的替代品来替代相应的螺金刚烷衍生物。

  DOI：

  10.1016/j.jphotochem.2010.12.001
• 作为产物：
  描述：

  3-甲氧基苯甲酸甲酯 在 劳森试剂 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 12.0h， 以84%的产率得到m-Methoxythiobenzoesaeure-O-methylester
  参考文献：
  名称：

  Synthesis of some fenchyl-substituted alkenes and enol-ethers containing 3-oxyphenyl substituents by the Barton-Kellogg reaction

  摘要：

  The synthesis of one fenchyl-substituted alkene and two enol-ethers, containing 3-oxyphenyl substituents by the Barton-Kellogg reaction is described. The tri-substituted aromatic fenchyl-alkene 1a was prepared in 53% yield from thiofenchone and a diazoanisole; whereas enol-ethers 1b and 1c were obtained (95 and 75% yield, respectively) using an inverse approach based on diazofenchone and aromatic thionoesters. A mixture of Z and E isomers was obtained in all cases; isomer attribution and quantification has been carried out by analysis of NMR spectroscopic data assisted by theoretical calculations (E/Z ratio: 1a = 0.72, 1b = 2.2, 1c = 1.8). Reaction proceeds with low stereoselectivity leading to the preferential formation of diastereoisomeric olefins and enol-ethers where the aromatic substituent resides at the side of the two fenchyl methyl groups.

  DOI：

  10.1590/s0103-50532010001000014

文献信息

• Compounds for treating and preventing cognitive diseases and depression
  申请人：Hoffmann-La Roche Inc.

  公开号：US05011849A1

  公开（公告）日：1991-04-30

  Ethylenediamine monoamides of the formula R--CO--NH--CH.sub.2 --CH.sub.2 --NH.sub.2 I wherein R is one of groups ##STR1## in which R.sup.1 is phenyl monohalophenyl, monolower-alkylphenyl, monolower-alkoxypheynl, monotrifluoromethylphenyl, monocyanophenyl or monoaryl-lower-alkoxyphenyl, dihalophenyl, furyl, thienyl or monohalothienyl, R.sup.2 is hydrogen, halogen or amino, R.sup.3, R.sup.5 and R.sup.7 each are phenyl, monohalophenyl, dihalophenyl, thienyl, furyl or monohalofuryl, R.sup.4 and R.sup.6 each are hydrogen or amino and R.sup.8 is hydrogen or lower-alkyl, as well as their pharmaceutically usable acid addition salts are disclosed. The compounds have monoamine oxidase inhibiting properties with low toxicity and are useful for the treatment of depressive states and cognitive disorders.

  公开了具有单胺氧化酶抑制性能且具有低毒性的乙二胺单酰胺化合物，其化学式为R--CO--NH--CH.sub.2 --CH.sub.2 --NH.sub.2，其中R是下列基团之一：##STR1## 其中R.sup.1为苯基、单卤苯基、单较低烷基苯基、单较低烷氧基苯基、单三氟甲基苯基、单氰基苯基或单芳基-较低烷氧基苯基、双卤苯基、呋喃基、噻吩基或单卤噻吩基，R.sup.2为氢、卤素或氨基，R.sup.3、R.sup.5和R.sup.7各自为苯基、单卤苯基、双卤苯基、噻吩基、呋喃基或单卤呋喃基，R.sup.4和R.sup.6各自为氢或氨基，R.sup.8为氢或较低烷基，以及它们的药用可用酸盐。这些化合物具有单胺氧化酶抑制性能，低毒性，可用于治疗抑郁状态和认知障碍。
• Synthesis of some fenchyl-substituted alkenes and enol-ethers containing 3-oxyphenyl substituents by the Barton-Kellogg reaction
  作者：Luiz Francisco M. L. Ciscato、Erick L. Bastos、Fernando H. Bartoloni、Wolfgang Günther、Dieter Weiss、Rainer Beckert、Wilhelm Josef Baader

  DOI：10.1590/s0103-50532010001000014

  日期：——

  The synthesis of one fenchyl-substituted alkene and two enol-ethers, containing 3-oxyphenyl substituents by the Barton-Kellogg reaction is described. The tri-substituted aromatic fenchyl-alkene 1a was prepared in 53% yield from thiofenchone and a diazoanisole; whereas enol-ethers 1b and 1c were obtained (95 and 75% yield, respectively) using an inverse approach based on diazofenchone and aromatic thionoesters. A mixture of Z and E isomers was obtained in all cases; isomer attribution and quantification has been carried out by analysis of NMR spectroscopic data assisted by theoretical calculations (E/Z ratio: 1a = 0.72, 1b = 2.2, 1c = 1.8). Reaction proceeds with low stereoselectivity leading to the preferential formation of diastereoisomeric olefins and enol-ethers where the aromatic substituent resides at the side of the two fenchyl methyl groups.
• Fenchyl substituted 1,2-dioxetanes as an alternative to adamantyl derivatives for bioanalytical applications
  作者：Luiz Francisco M.L. Ciscato、Dieter Weiss、Rainer Beckert、Wilhelm J. Baader

  DOI：10.1016/j.jphotochem.2010.12.001

  日期：2011.2

  and study of the chemiluminescence parameters and thermal stability of 1,2-dioxetanes containing a spirofenchyl substituent are reported. Three fenchyl-substituted 1,2-dioxetanes were synthesized by photooxygenation of the corresponding alkenes, obtained by Barton–Kellogg olefination of the readily available (−)-fenchone. The fenchyl-substituted 1,2-dioxetanes showed thermal stabilities similar to those

  报道了含螺甲醚基取代基的1,2-二氧杂环丁烷的化学发光参数和热稳定性的合成和研究。通过相应的烯烃的光氧合反应合成了三个芬基取代的1,2-二氧杂环丁烷，这些烯烃是通过易得的（-）-芬酮的巴顿-凯洛格烯化反应制得的。芬基取代的1,2-二氧杂环丁烷显示出与相应的螺金刚烷基取代的衍生物相似的热稳定性，尽管在单分子分解方面比后一种衍生物稍不稳定，后者在多种化学发光中被广泛用作标记免疫测定。氟化物诱导的一种可触发的1,1,2-二氟苯醚衍生物的分解显示出与相应的金刚烷基取代的衍生物相似的动力学参数。在1％范围内的化学发光量子产率也与其他广泛使用的化学发光系统的鲁米诺反应相似。这些结果表明，在生物分析应用中，芬基取代的1，2-二氧杂环丁烷可以潜在地用作便宜的替代品来替代相应的螺金刚烷衍生物。