methyl 8-(2-(2,5-dimethylphenyl)acetamido)-1,4-dioxaspiro[4.5]decane-8-carboxylate | 907187-56-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 8-(2-(2,5-dimethylphenyl)acetamido)-1,4-dioxaspiro[4.5]decane-8-carboxylate
• 英文别名: Methyl 8-[[2-(2,5-dimethylphenyl)acetyl]amino]-1,4-dioxaspiro[4.5]decane-8-carboxylate
• CAS: 907187-56-8
• 化学式: C₂₀H₂₇NO₅
• 分子量: 361.438
• InChiKey: GSHLRHOIPXYCNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 8-(2-(2,5-dimethylphenyl)acetamido)-1,4-dioxaspiro[4.5]decane-8-carboxylate 在 盐酸 、 potassium tert-butylate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-(2,5-dimethylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione
  参考文献：
  名称：

  Design, Synthesis, and Analysis of the Quantitative Structure–Activity Relationships of 4-Phenyl-acyl-substituted 3-(2,5-Dimethylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione Derivatives

  摘要：

  A series of 4-phenyl-acyl-substituted 3-(2,5-dimethylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione derivatives were designed and synthesized, and their structures were characterized using H-1 NMR (or C-13 NMR), mass spectrometry, and elemental analysis. The bioactivities of the new compounds were evaluated. These compounds exhibited good inhibition activities against bean aphids (Aphis fabae) and carmine spider mite (Tetranychus cinnabarinus), and 4-phenyl acyl esters showed stronger bioactivity than 4-arylesterases and alkyl esters. The results showed that compound 8-I-e, which contains a para-methoxy group on the phenyl acyl, and compound 8-I-m, which contains a para-trifluoromethyl group on the phenyl acyl, displayed potent insecticidal activity against A. fabae and T. cinnabarinus respectively. The insecticidal activity showed a clear structure-activity relationship, confirming the importance of the flexible bridge. The DFT/B3LYP/6-31(d) level method was used to calculate molecular geometries and electronic descriptors. These factors included total energy, charge distribution, and the linear orbital level of the title compounds. Quantitative structure-activity relationship studies were performed on these compounds using quantum-chemical and physicochemical parameters as independent variables and insecticidal activity as a dependent variable. Insecticidal activity was most closely correlated (r > 0.8) with quantum chemical and physicochemical parameters.

  DOI：

  10.1021/jf3002069
• 作为产物：
  描述：

  1-氨基-4-恶环己烷羧酸乙烯 在 氯化亚砜 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.2h， 生成 methyl 8-(2-(2,5-dimethylphenyl)acetamido)-1,4-dioxaspiro[4.5]decane-8-carboxylate
  参考文献：
  名称：

  螺酮缩醇取代的环状酮烯醇

  摘要：

  本发明涉及其中A、B、Q1、Q2、D、G、W、X、Y和Z具有给出定义的式(I)的新的螺酮缩醇取代的环状酮烯醇、制备其的方法和中间体以及其作为杀虫剂和/或杀微生物剂和/或除草剂的用途。本发明还涉及含有螺酮缩醇取代的环状酮烯醇和一种提高栽培植物相容性的化合物的选择性除草剂。

  公开号：

  CN101160049B

文献信息

• 螺酮缩醇取代的环状酮烯醇
  申请人：拜耳知识产权有限责任公司

  公开号：CN101160049B

  公开（公告）日：2016-05-11

  本发明涉及其中A、B、Q1、Q2、D、G、W、X、Y和Z具有给出定义的式(I)的新的螺酮缩醇取代的环状酮烯醇、制备其的方法和中间体以及其作为杀虫剂和/或杀微生物剂和/或除草剂的用途。本发明还涉及含有螺酮缩醇取代的环状酮烯醇和一种提高栽培植物相容性的化合物的选择性除草剂。
• Spiroketal-Substituted Cyclic Ketoenols
  申请人：Bretschneider Thomas

  公开号：US20080305955A1

  公开（公告）日：2008-12-11

  The invention relates to novel spiroketal-substituted cyclic ketoenols of the formula (I) in which A, B, Q 1 , Q 2 , D, G, W, X, Y, and Z are as defined above, to processes and intermediates for their preparation and to their use as pesticides and/or microbicides and/or herbicides. Moreover, the invention relates to selective herbicidal compositions comprising, firstly, spiroketal-substituted cyclic ketoenols and, secondly, a crop plant compatibility-improving compound.
• US7897543B2
  申请人：——

  公开号：US7897543B2

  公开（公告）日：2011-03-01
• Design, Synthesis, and Analysis of the Quantitative Structure–Activity Relationships of 4-Phenyl-acyl-substituted 3-(2,5-Dimethylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione Derivatives
  作者：Jinhao Zhao、Jiangong Zhang、Bingrong Xu、Zongcheng Wang、Jingli Cheng、Guonian Zhu

  DOI：10.1021/jf3002069

  日期：2012.5.16

  A series of 4-phenyl-acyl-substituted 3-(2,5-dimethylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione derivatives were designed and synthesized, and their structures were characterized using H-1 NMR (or C-13 NMR), mass spectrometry, and elemental analysis. The bioactivities of the new compounds were evaluated. These compounds exhibited good inhibition activities against bean aphids (Aphis fabae) and carmine spider mite (Tetranychus cinnabarinus), and 4-phenyl acyl esters showed stronger bioactivity than 4-arylesterases and alkyl esters. The results showed that compound 8-I-e, which contains a para-methoxy group on the phenyl acyl, and compound 8-I-m, which contains a para-trifluoromethyl group on the phenyl acyl, displayed potent insecticidal activity against A. fabae and T. cinnabarinus respectively. The insecticidal activity showed a clear structure-activity relationship, confirming the importance of the flexible bridge. The DFT/B3LYP/6-31(d) level method was used to calculate molecular geometries and electronic descriptors. These factors included total energy, charge distribution, and the linear orbital level of the title compounds. Quantitative structure-activity relationship studies were performed on these compounds using quantum-chemical and physicochemical parameters as independent variables and insecticidal activity as a dependent variable. Insecticidal activity was most closely correlated (r > 0.8) with quantum chemical and physicochemical parameters.