Dimethyl 3-isopropylisoxazole-4,5-dicarboxylate | 134516-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Dimethyl 3-isopropylisoxazole-4,5-dicarboxylate
• 英文别名: dimethyl 3-propan-2-yl-1,2-oxazole-4,5-dicarboxylate
• CAS: 134516-28-2
• 化学式: C₁₀H₁₃NO₅
• 分子量: 227.217
• InChiKey: KSJOCMFYDHYOOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Dimethyl 3-isopropylisoxazole-4,5-dicarboxylate 在 sodium hydroxide 、 氯化亚砜 作用下， 生成
  参考文献：
  名称：

  Synthesis and herbicidal activity of isoxazoledicarboxylic acid derivatives

  摘要：

  AbstractStarting from bulk chemicals, novel isoxazoledicarboxylic acid esters were prepared and converted to the corresponding dicarboxylic acid mono‐amides in a few reaction steps and in high overall yields. Key intermediates for the cycloaddition step were chlorooximinoacetates or amides as nitrile oxide equivalents, prepared in one‐pot reactions from diketene or acetoacetic acid esters. Isoxazoledicarboxylic acid monoamides combined good herbicidal activity with chemical flexibility. They were characterized as inhibitors of photosynthesis. Particularly, they affected the photosynthetic electron transport in photosystem II and the rate of carbon dioxide assimilation. Applied post‐emergence, the new compounds were found to control a broad spectrum of key weeds in corn. Excellent activity was found on Abutilon theophrasti (L.) Medik., Amaranthus retroflexus L., Chenopodium album L., Ipomoea spp., Polygonum persicaria L., Solanum nigrum L. and Xanthium strumarium L. with rates between 0.2 and 0.5 kg ha−1. As a side‐effect, the compounds also showed activity against grass weeds. The compounds are excellent tank‐mix partners, e.g. for sulfonyl‐ureas, to complete the weed spectrum (Chenopodium album L., Solanum nigrum L.) and/or to reduce the risk of developing herbicide‐resistant weeds.

  DOI：

  10.1002/ps.2780440104
• 作为产物：
  描述：

  異丁醛肟 、 1,4-dimethyl but-2-enedioate 在 sodium hypochlorite 作用下， 生成 Dimethyl 3-isopropylisoxazole-4,5-dicarboxylate
  参考文献：
  名称：

  Synthesis and herbicidal activity of isoxazoledicarboxylic acid derivatives

  摘要：

  AbstractStarting from bulk chemicals, novel isoxazoledicarboxylic acid esters were prepared and converted to the corresponding dicarboxylic acid mono‐amides in a few reaction steps and in high overall yields. Key intermediates for the cycloaddition step were chlorooximinoacetates or amides as nitrile oxide equivalents, prepared in one‐pot reactions from diketene or acetoacetic acid esters. Isoxazoledicarboxylic acid monoamides combined good herbicidal activity with chemical flexibility. They were characterized as inhibitors of photosynthesis. Particularly, they affected the photosynthetic electron transport in photosystem II and the rate of carbon dioxide assimilation. Applied post‐emergence, the new compounds were found to control a broad spectrum of key weeds in corn. Excellent activity was found on Abutilon theophrasti (L.) Medik., Amaranthus retroflexus L., Chenopodium album L., Ipomoea spp., Polygonum persicaria L., Solanum nigrum L. and Xanthium strumarium L. with rates between 0.2 and 0.5 kg ha−1. As a side‐effect, the compounds also showed activity against grass weeds. The compounds are excellent tank‐mix partners, e.g. for sulfonyl‐ureas, to complete the weed spectrum (Chenopodium album L., Solanum nigrum L.) and/or to reduce the risk of developing herbicide‐resistant weeds.

  DOI：

  10.1002/ps.2780440104

文献信息

• In Situ Generation of Nitrile Oxides from NaCl–Oxone Oxidation of Various Aldoximes and Their 1,3-Dipolar Cycloaddition
  作者：Guodong Zhao、Lixin Liang、Chi Ho Ethan Wen、Rongbiao Tong

  DOI：10.1021/acs.orglett.8b03829

  日期：2019.1.4

  generation of nitrile oxides through NaCl/Oxone oxidation of aldoximes and their dipolar cycloaddition. The key feature is the use of a green chemistry approach to address the substrate scope of aldoximes: broad scope (aliphatic, aromatic, and alkenyl aldoximes) without production of organic byproducts derived from oxidant and/or catalyst. Importantly, NaCl/Oxone-promoted three-component cycloaddition of aldehyde

  据报道，这是一种新的绿色方案，可通过醛固酮的NaCl / Oxone氧化及其偶极环加成反应有效地原位生成腈氧化物。关键特征是使用绿色化学方法解决了醛肟的底物范围：广泛的范围（脂族，芳族和烯基醛肟），而不会产生衍生自氧化剂和/或催化剂的有机副产物。重要的是，NaCl / Oxone促进了醛，盐酸羟胺和烯烃的三组分环加成反应（63-81％）。
• Cyanoisoxazoles
  申请人：BASF Aktiengesellschaft

  公开号：US05543416A1

  公开（公告）日：1996-08-06

  Cyanoisoxazoles of the formula Ia or Ib ##STR1## where R.sup.1 is hydrogen, alkyl, cycloalkyl, phenyl; R.sup.2 is hydrogen, alkyl, cycloalkyl and R.sup.3 is alkoxy, alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl or phenyl, it being possible for the organic radicals mentioned under R.sup.1, R.sup.2 and R.sup.3 to be substituted in each case. The compounds of the Formula Ia or Ib are useful as herbicides.

  公式Ia或Ib的氰基异噁唑化合物##STR1##其中，R.sup.1为氢，烷基，环烷基，苯基；R.sup.2为氢，烷基，环烷基，R.sup.3为烷氧基，烷基，环烷基，环烯基，烯基，炔基或苯基，R.sup.1，R.sup.2和R.sup.3下所提到的有机基团在每种情况下均可被取代。公式Ia或Ib的化合物可用作除草剂。
• US5473069A
  申请人：——

  公开号：US5473069A

  公开（公告）日：1995-12-05
• US5543416A
  申请人：——

  公开号：US5543416A

  公开（公告）日：1996-08-06