1-(1,3-difluoro-5,6,7,8-tetrahydro-5,5-dimethyl-2-naphthalenyl)ethanone | 156868-39-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-(1,3-difluoro-5,6,7,8-tetrahydro-5,5-dimethyl-2-naphthalenyl)ethanone
• 英文别名: 1-(1,3-difluoro-5,5-dimethyl-7,8-dihydro-6H-naphthalen-2-yl)ethanone
• CAS: 156868-39-2
• 化学式: C₁₄H₁₆F₂O
• 分子量: 238.277
• InChiKey: OXMMFDJZWKVXQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1,3-difluoro-5,6,7,8-tetrahydro-5,5-dimethyl-2-naphthalenyl)ethanone 在 lithium diisopropyl amide 作用下， 生成 1-[2-(1,3-difluoro-5,5-dimethyl-7,8-dihydro-6H-naphthalen-2-yl)ethynyl]cyclohexan-1-ol
  参考文献：
  名称：

  Synthesis and herbicidal activity of phenylproparginols.

  摘要：

  A three-step/one-pot procedure was developed for preparing herbicidal fluorophenylproparginols from acetophenones by way of an enol phosphate intermediate. Side-by-side testing of 16 of the more active analogs showed that trans-2-methyl-1-[2-(4-methoxy-2,3,5,6-tetrafluorophenyl)ethynyl]cyclohexanol (21c) was the most potent example. On the basis of the biological response data obtained for these first-tier analogs, a physiochemical ''structural space'' was defined. Twenty additional analogs were then targeted for synthesis in an experimental design set up to probe that structural space. Scaled rank sums analysis of herbicidal activity for these second-tier analogs produced a quantitative structure/activity relationship model indicating that 21c bears a substitution pattern that is at or near the optimum for this class of chemistry.

  DOI：

  10.1021/jf00047a043
• 作为产物：
  描述：

  2,4-二氟溴苄 在 吡啶 、 三氯化铝 、 三溴化磷 、 magnesium 、 1,2-二溴乙烷 作用下， 以 1,2-二氯乙烷 、 苯 为溶剂， 反应 102.0h， 生成 1-(1,3-difluoro-5,6,7,8-tetrahydro-5,5-dimethyl-2-naphthalenyl)ethanone
  参考文献：
  名称：

  四氢萘的合成。第二部分

  摘要：

  描述了利用环脱水方法的合成，以制备在芳香环的每个位置上被官能团取代并且在非芳香环的1-位上被多个烷基取代的新型四氢萘。

  DOI：

  10.1016/s0040-4020(01)87011-3

文献信息

• Synthesis and Herbicidal Activity of Substituted Tetrahydronaphthalenes (Part II)
  作者：John J. Parlow、Martin D. Mahoney

  DOI：10.1002/(sici)1096-9063(199603)46:3<227::aid-ps358>3.0.co;2-v

  日期：1996.3

  This paper reports the synthesis and the biological activity of novel tetrahydronaphthalenes with substitution of functional groups at each position of the aromatic ring and substitution of various alkyl groups at the 1-position of the non-aromatic ring. These compounds exhibited pre-emergent herbicidal activity which was determined by the orientation and type of functional groups on the aromatic ring with the 1,1-dimethyl substitution on the non-aromatic ring. The activity tended to be highest for nitro or methyl at the 5- and 7-positions with an amino or ester group at the 6-position and a dimethyl substitution at the 1-position.
• Parlow John J., Clark Robert D., J. Agr. and Food Chem, 42 (1994) N 11, S 2600-2609
  作者：Parlow John J., Clark Robert D.

  DOI：——

  日期：——
• Syntheses of tetrahydronaphthalenes. Part II
  作者：John J. Parlow

  DOI：10.1016/s0040-4020(01)87011-3

  日期：1994.3

  Syntheses utilizing the cyclodehydration method to prepare novel tetrahydronaphthalenes substituted with functional groups at each position of the aromatic ring and various alkyl groups at the 1-position of the non-aromatic ring are described.

  描述了利用环脱水方法的合成，以制备在芳香环的每个位置上被官能团取代并且在非芳香环的1-位上被多个烷基取代的新型四氢萘。
• Synthesis and herbicidal activity of phenylproparginols.
  作者：John J. Parlow、Robert D. Clark

  DOI：10.1021/jf00047a043

  日期：1994.11

  A three-step/one-pot procedure was developed for preparing herbicidal fluorophenylproparginols from acetophenones by way of an enol phosphate intermediate. Side-by-side testing of 16 of the more active analogs showed that trans-2-methyl-1-[2-(4-methoxy-2,3,5,6-tetrafluorophenyl)ethynyl]cyclohexanol (21c) was the most potent example. On the basis of the biological response data obtained for these first-tier analogs, a physiochemical ''structural space'' was defined. Twenty additional analogs were then targeted for synthesis in an experimental design set up to probe that structural space. Scaled rank sums analysis of herbicidal activity for these second-tier analogs produced a quantitative structure/activity relationship model indicating that 21c bears a substitution pattern that is at or near the optimum for this class of chemistry.