3-chlorobenzyne | 85683-73-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 3-chlorobenzyne
• 英文别名: 3-Chlor-dehydrobenzol；Chlorobenzyne；1-chlorocyclohexa-1,3-dien-5-yne
• CAS: 85683-73-4
• 化学式: C₆H₃Cl
• 分子量: 110.543
• InChiKey: SXMSDFCHAGYKLG-UHFFFAOYSA-N

物化性质

• 沸点：
  143.8±29.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,6-dichlorophenyllithium 以 四氢呋喃 、 甲苯 为溶剂， 生成 3-chlorobenzyne
  参考文献：
  名称：

  Structural and Rate Studies of the Formation of Substituted Benzynes

  摘要：

  The key elimination step for the formation of 3-substituted and 3,6-disubstituted benzynes from 2-haloaryllithiums displays a pronounced solvent-dependent regioselectivity. All 2-haloaryllithiums with electron withdrawing groups in the 6 position are shown by Li-6 and C-13 NMR spectroscopic studies to be monomers in THF. DFT computational studies implicate trisolvates. Rate studies reveal that LiF eliminates via monomer-based pathways requiring THF dissociation whereas LiCl eliminates via nondissociative pathways. Elimination to form 3-chloro- and 3-fluorobenzyne from 2-chloro-6-fluorophenyllithium displays a pronounced solvent-dependent regioselectivity that is traced to competing solvent-dissociative and nondissociative dissociative pathways for the elimination of LiCl and LiF, respectively.

  DOI：

  10.1021/ja0754655

文献信息

• Formation of Benzynes from 2,6-Dihaloaryllithiums:  Mechanistic Basis of the Regioselectivity
  作者：Antonio Ramírez、John Candler、Crystal G. Bashore、Michael C. Wirtz、Jotham W. Coe、David B. Collum

  DOI：10.1021/ja044899m

  日期：2004.11.1

  The key elimination step for the formation of 3-chloro- and 3-fluorobenzyne from 2-chloro-6-fluorophenyllithium displays a pronounced solvent-dependent regioselectivity. 6Li and 13C NMR spectroscopic studies on 2-chloro-6-fluorophenyllithium reveal a single monomeric aryllithium, suggested by DFT computational studies to be a trisolvate. Rate studies indicate that the elimination of LiCl and LiF proceeds

  从 2-氯-6-氟苯基锂形成 3-氯-和 3-氟苄的关键消除步骤显示出明显的溶剂依赖性区域选择性。2-氯-6-氟苯基锂的 6Li 和 13C NMR 光谱研究揭示了单一单体芳基锂，DFT 计算研究表明它是一种三溶剂化物。速率研究表明 LiCl 和 LiF 的消除分别通过三溶剂化和二溶剂化单体进行。
• 1-Oxohydrocarbyl-substituted azacyclohexanes compositions used as acid catalyst
  申请人：WHITBY RESEARCH, Inc.

  公开号：EP0582065A1

  公开（公告）日：1994-02-09

  This invention provides a process for the conversion of a reactant into a reaction product in the presence of an acid catalyst which comprises contacting said reactant with an acid catalyst comprising a compound represented by the general formula wherein X may represent sulfur, oxygen or nitrogen; a and b may be 0 or 1, c may be 0,1 or 2, except that when X is oxygen, a, b and c are O, when X is nitrogen c is 0 and only one of a or b is 1, and when X is sulfur a and b are 0; A is a branched or a straight chain, divalent aliphatic radical having from 0 to 2 double bonds; R' is selected from the group consisting of H, a lower alkyl group having from 1 to 4 carbon atoms, phenyl, lower alkyl or halogen substituted phenyl, acetamido, halogen, piperidinyl, lower alkyl or halogen substituted piperidinyl, carbalkoxy, carboxamide, and alkanoyl; and R is hydrogen or a lower alkyl group having from 1 to 4 carbon atoms, wherein R'' is H or halogen, and salts thereof, and Z is selected from the group consisting of anions of strong acids.

  本发明提供了一种在酸催化剂存在下将反应物转化为反应产物的工艺，该工艺包括将所述反应物与酸催化剂接触，酸催化剂由通式所代表的化合物组成。 其中 X 可以代表硫、氧或氮；a 和 b 可以是 0 或 1，c 可以是 0、1 或 2，但当 X 是氧时，a、b 和 c 是 O，当 X 是氮时，c 是 0，a 或 b 中只有一个是 1，当 X 是硫时，a 和 b 是 0；A 是支链或直链二价脂族基，具有 0 至 2 个双键；R'选自由 H、具有 1 至 4 个碳原子的低级烷基、苯基、低级烷基或卤素取代的苯基、乙酰氨基、卤素、哌啶基、低级烷基或卤素取代的哌啶基、碳烷氧基、羧酰胺和烷酰基组成的组；以及 R 为氢或具有 1 至 4 个碳原子的低级烷基、 其中 R''是氢或卤素，以及它们的盐，Z 选自强酸阴离子组成的组。
• Method for improved plant pest control
  申请人：Whitby Research Incorporated

  公开号：EP0077078B1

  公开（公告）日：1986-10-15
• COMPOSITIONS COMPRISING 1-SUBSTITUTED AZACYCLOALKANES AND THEIR USES
  申请人：Whitby Research Incorporated

  公开号：EP0257063A1

  公开（公告）日：1988-03-02
• EP0257063A4
  申请人：——

  公开号：EP0257063A4

  公开（公告）日：1989-04-24