1-chloropiperidine-2,6-dione | 82621-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-chloropiperidine-2,6-dione
• 英文别名: N-chloroglutarimide
• CAS: 82621-82-7
• 化学式: C₅H₆ClNO₂
• 分子量: 147.561
• InChiKey: ADFIFDHDLIZVFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-chloropiperidine-2,6-dione 在 水 作用下， 生成 戊二酰亚胺
  参考文献：
  名称：

  The Return of the Succinimidyl Radical.

  摘要：

  The aqueous kinetics of the succinimidyl radical. S-. has been re-examined in the presence of oxidizable substrates and oxygen. The results indicate a rapid equilibrium between S-. and its ring-opened analogue, the beta B-(isocyanatocarbonyl)ethyl radical, PI.. The equilibrium constant K-1, is ca, 10, with k(1) approximate to 10(7) s(-1) and k(-1) approximate to 10(6) s(-1). The glutarimidyl radical, G(.), was produced by one-electron reduction of N-chloroglutarimide, GCI. The rate constants of several oxidation and hydrogen abstraction reactions with S-. and G(.) have been determined. Furthermore. halogen abstraction reactions from haloimides by some selected alkyl radicals were also scrutinised. Most striking is the finding that the 2-cyanoethyl radical abstracts Br from SBr ca. 25 times slower than does the ethyl radical. This demonstrates a strong beta-effect and rationalises a relatively slow Br abstraction rate by PI. from SBr. While the closure rate of the PI. radical appears to be solvent-insensitive, the ring opening rate of S-., k(1), is estimated to be ca. 100 times faster in, e.g., CH2Cl2, than in water. This suggests hydrogen-bonded stabilisation of S-..

  DOI：

  10.3891/acta.chem.scand.52-0062
• 作为产物：
  描述：

  戊二酰亚胺 在 三氯异氰尿酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以63%的产率得到1-chloropiperidine-2,6-dione
  参考文献：
  名称：

  通过分子间自由基加成到AIBN衍生物的腈基上来合成Am衍生物

  摘要：

  据报道，通过将氮中心自由基分子间加成到腈中来合成am衍生物。进行了实验研究和密度泛函理论计算以探讨该反应的机理。结果表明，烷基腈通过吸引氯原子而被激活，随后被以氮为中心的自由基所攻击，从而导致腈在分子间的自由基加成到idine上。

  DOI：

  10.1055/a-1344-6175

文献信息

• TETRAZOLINONE COMPOUND AND USE OF SAME
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20160081339A1

  公开（公告）日：2016-03-24

  A tetrazolinone compound of formula (1): wherein R 1 and R 2 each independently represents a hydrogen atom, etc.; R 3 represents a C1-C6 alkyl group, etc.; R 4 , R 5 , and R 6 each independently represents a hydrogen atom, etc.; A represents a C6-C16 aryl group optionally having one or more atoms or groups selected from Group P, etc.; Q represents the following group Q1, etc.; and X represents an oxygen atom or a sulfur atom, has excellent control activity against pests.

  一种化学式（1）所示的四唑酮化合物： 其中R1和R2分别独立表示氢原子，等等； R3表示C1-C6烷基，等等；R4、R5和R6分别独立表示氢原子，等等；A表示一个C6-C16芳基，可选地具有来自P族等组的一个或多个原子或基团；Q表示以下Q1组等；以及 X表示氧原子或硫原子，对害虫具有出色的控制活性。
• [EN] TETRAZOLINONE COMPOUNDS AND ITS USE AS PESTICIDES<br/>[FR] COMPOSÉS DE TÉTRAZOLINONE ET LEUR UTILISATION EN TANT QUE PESTICIDES
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2013162072A1

  公开（公告）日：2013-10-31

  The present invention provides a compound having an excellent efficacy for controlling pests. A tetrazolinone compound of a formula (1): [wherein R1 represents an C6-C16 aryl group, an C1-C12 alkyl group, or a C3-C12 cycloalkyl group, etc., which each optionally be substituted; R2, R3, R4 and R5 represent independently of each other a hydrogen atom, a halogen atom or an C1-C3 alkyl group, etc.; R6 represents an C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, a C1-C6 haloalkyl group, an C2-C6 alkenyl group, an C1-C6 alkoxy group, or a C1-C6 haloalkoxy group, etc.; R7, R8 and R9 represent independently of each other a hydrogen atom, a halogen atom, or an C1-C4 alkyl group, etc.; X represents an oxygen atom or a sulfur atom; and R10 represents an C1-C6 alkyl group, etc.] shows an excellent controlling efficacy on pests.

  本发明提供了一种具有优异杀虫效果的化合物。公式（1）的四唑酮化合物：[其中R1代表C6-C16芳基、C1-C12烷基或C3-C12环烷基等，每个都可以选择性地被取代；R2、R3、R4和R5分别独立地代表氢原子、卤素原子或C1-C3烷基等；R6代表C1-C6烷基、C3-C6环烷基、卤素原子、C1-C6卤代烷基、C2-C6烯基、C1-C6烷氧基或C1-C6卤代烷氧基等；R7、R8和R9分别独立地代表氢原子、卤素原子或C1-C4烷基等；X代表氧原子或硫原子；R10代表C1-C6烷基等]在杀虫方面表现出优异的控制效果。
• Cyclisation of ω-(isocyanatocarbonyl)alkyl radicals: acyclic precursors of imidyl radicals
  作者：Parveen Kaushal、Brian P. Roberts

  DOI：10.1039/p29890001559

  日期：——

  2,2-dimethylsuccinimidyl radical which subsequently undergoes rin opening to yield Me2ĊCH2C(O)NCO (15). The overall rearrangement of (14) to (15) represents 1,2-shift of the –C(O)NCO group via an intermediate imidyl radical. The glutarimidyl radical is forme by 1,6-endo cyclisation of H2ĊCH2CH2C(O)NCO. It is proposed that the rapid cyclisation of ω-isocyanatoalkyl radicals provides strong evidence

  由N-卤代亚胺的光解或卤素原子的提取生成的亚胺基自由基在Bu 2 t C CH 2的有效捕集下得到了相对持久的加合物，这已通过es光谱学进行了研究。溴原子抽象从BRCH 2 CH 2 C（O）NCO（2）得到ħ 2 CCH 2 C（O）NCO（1），其经历快速1,5-内切环化，得到琥珀酰亚胺基团。已使用esr光谱结合Bu 2 t C CH 2的自旋阱对这种环化进行了研究。和BU吨Ñ O.为（环化率系数1）已被估计为3.7×10 6小号-1在环己烷328ķ从（之间的自由基链式反应的产物的分析2）的triethylgermane。ESR和产物的分析研究表明，ħ 2 CCME 2 C（O）NCO（14）cyclises，MOR速度比（1），得到2,2- dimethylsuccinimidyl基团，其随后经历RIN开口，得到我2 CCH 2 Ç （O）NCO（15）。（14）至（15）的整体重排
• TETRAZOLINONE COMPOUNDS AND APPLICATIONS THEREOF
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20160150787A1

  公开（公告）日：2016-06-02

  A tetrazolinone compound represented by formula (1): wherein Q represents a 6-membered aromatic heterocyclic group optionally having one or more atoms or groups selected from Group P 1 , provided that a heteroatom constituting the heterocyclic group is a nitrogen atom, and the number of nitrogen atom is 1, 2, or 3; R 1 , R 2 , R 3 , and R 11 each represents a C1-C6 alkyl group optionally having one or more atoms or groups selected from Group P 2 ; R 4 and R 5 each represents a hydrogen atom, etc.; R 6 represents a C1-C6 alkyl group optionally having one or more halogen atoms, etc.; R 7 , R 8 , and R 9 each represents a hydrogen atom, etc.; and X represents an oxygen atom or a sulfur atom, has excellent control activity against pests.

  一种由式（1）表示的四唑酮化合物：其中Q代表一个6元芳香杂环基，可选地具有来自P1组的一个或多个原子或基团，前提是构成杂环基的杂原子为氮原子，且氮原子的数量为1、2或3；R1、R2、R3和R11分别代表一个C1-C6烷基基团，可选地具有来自P2组的一个或多个原子或基团；R4和R5各代表一个氢原子，等等；R6代表一个C1-C6烷基基团，可选地具有一个或多个卤原子，等等；R7、R8和R9各代表一个氢原子，等等；X代表一个氧原子或硫原子，对害虫具有出色的控制活性。
• [EN] TETRAZOLINONE COMPOUNDS AND ITS USE<br/>[FR] COMPOSÉS DE TÉTRAZOLINONE ET LEUR UTILISATION
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2013162077A1

  公开（公告）日：2013-10-31

  The present invention provides a compound having an excellent efficacy for controlling pests. A tetrazolinone compound of a formula (1): [wherein, R1 represents an C6-C16 aryl group, an C1-C12 alkyl group, a C3-C12 cycloalkyl group or an adamantyl group, etc., which each optionally be substituted; R2 represents a hydrogen atom, an C1-C12 alkyl group, or a halogen atom, etc.; R4 and R5 represent independently of each other a hydrogen atom or an C1-C3 alkyl group, etc.; R6, R7, R8 and R9 represent independently of each other a hydrogen atom, a halogen atom, an C1-C12 alkyl group, a C1-C12 haloalkyl group, an C2-C12 alkenyl group, a C3-C12 cycloalkyl group, an C1-C12 alkoxy group or a C1-C12 haloalkoxy group, etc.; X and Y represent independently of each other a sulfur atom or an oxygen atom; Q represents an oxygen atom or a sulfur atom; and R10 represents an C1-C6 alkyl group, etc.] shows an excellent controlling efficacy on pests.

  本发明提供了一种具有优异杀虫效果的化合物。式（1）中的四氮杂酮化合物：[其中，R1代表一个C6-C16芳基，一个C1-C12烷基，一个C3-C12环烷基或一个金刚烷基等，每个都可以选择性地被取代；R2代表一个氢原子，一个C1-C12烷基或一个卤素原子等；R4和R5分别独立地代表一个氢原子或一个C1-C3烷基等；R6、R7、R8和R9分别独立地代表一个氢原子，一个卤素原子，一个C1-C12烷基，一个C1-C12卤代烷基，一个C2-C12烯基，一个C3-C12环烷基，一个C1-C12烷氧基或一个C1-C12卤代烷氧基等；X和Y分别独立地代表一个硫原子或一个氧原子；Q代表一个氧原子或一个硫原子；R10代表一个C1-C6烷基等]对害虫有极佳的控制效果。