5-Chloro-1-hydrazono-2-hydroxy-indan-2-carboxylic acid methyl ester | 144172-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-Chloro-1-hydrazono-2-hydroxy-indan-2-carboxylic acid methyl ester
• 英文别名: Methyl 5-chloro-1-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylate；methyl (3Z)-6-chloro-3-hydrazinylidene-2-hydroxy-1H-indene-2-carboxylate
• CAS: 144172-26-9
• 化学式: C₁₁H₁₁ClN₂O₃
• 分子量: 254.673
• InChiKey: JCVOGCGLEKVMAX-ZROIWOOFSA-N

物化性质

• 沸点：
  410.2±55.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)
• 溶解度：
  二氯甲烷；二甲基亚砜；乙酸乙酯;甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2928000090

反应信息

• 作为产物：
  描述：

  5-氯-1-氧代-2,3-二氢-1H-茚-2-羧酸甲酯 在 溶剂黄146 、 间氯过氧苯甲酸 、 肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 5-Chloro-1-hydrazono-2-hydroxy-indan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  The discovery of indoxacarb: oxadiazines as a new class of pyrazoline-type insecticides

  摘要：

  The evolution of the insecticidal pyrazoline moiety that was originally discovered in 1972 has led to the discovery of a new crop insecticide, indoxacarb, which is the first commercialized pyrazoline-type sodium-channel blocker. Both monocyclic and fused-tricyclic pyrazolines and pyridazines, as well as structurally related semicarbazones were examined prior to the discovery of analogous tricyclic oxadiazines which had similarly high activity as well as favorable environmental dissipation rates and low toxicity to non-target organisms. The eventual leading candidate, DPX-JW062, was originally obtained as a racemic molecule, but a chiral synthesis was developed which produces material that is 50% ee in the insecticidal (+)-S-enantiomer (DPX-MP062, indoxacarb). (C) 2001 Society of Chemical Industry.

  DOI：

  10.1002/1526-4998(200102)57:2<153::aid-ps288>3.0.co;2-o

文献信息

• AN ARTHROPODICIDAL OXADIAZINE INTERMEDIATE
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0819114A1

  公开（公告）日：1998-01-21
• US5602251A
  申请人：——

  公开号：US5602251A

  公开（公告）日：1997-02-11
• [EN] AN ARTHROPODICIDAL OXADIAZINE INTERMEDIATE<br/>[FR] INTERMEDIAIRE D'OXADIAZINE ARTHROPODICIDE
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：WO1996031467A1

  公开（公告）日：1996-10-10

  (EN) Provided is a compound of formula (I). This compound is an intermediate to and is used for preparing the arthropodicidal oxidiazine Compound (II) described in the specification.(FR) L'invention décrit un composé de formule (I). Ce composé est un intermédiaire et est utilisé pour la préparation du composé (II) d'oxadiazine arthropodicide décrit dans la description.
• The discovery of indoxacarb: oxadiazines as a new class of pyrazoline-type insecticides
  作者：Stephen F McCann、Gary D Annis、Rafael Shapiro、David W Piotrowski、George P Lahm、Jeffery K Long、Kevin C Lee、Margaret M Hughes、Brian J Myers、Sandra M Griswold、Bonita M Reeves、Robert W March、Paula L Sharpe、Patrick Lowder、William E Barnette、Keith D Wing

  DOI：10.1002/1526-4998(200102)57:2<153::aid-ps288>3.0.co;2-o

  日期：2001.2

  The evolution of the insecticidal pyrazoline moiety that was originally discovered in 1972 has led to the discovery of a new crop insecticide, indoxacarb, which is the first commercialized pyrazoline-type sodium-channel blocker. Both monocyclic and fused-tricyclic pyrazolines and pyridazines, as well as structurally related semicarbazones were examined prior to the discovery of analogous tricyclic oxadiazines which had similarly high activity as well as favorable environmental dissipation rates and low toxicity to non-target organisms. The eventual leading candidate, DPX-JW062, was originally obtained as a racemic molecule, but a chiral synthesis was developed which produces material that is 50% ee in the insecticidal (+)-S-enantiomer (DPX-MP062, indoxacarb). (C) 2001 Society of Chemical Industry.