1-Chloromethyl-2-ethynyl-benzene | 10601-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Chloromethyl-2-ethynyl-benzene
• 英文别名: 1-(Chloromethyl)-2-ethynylbenzene
• CAS: 10601-96-4
• 化学式: C₉H₇Cl
• mdl: MFCD19233645
• 分子量: 150.608
• InChiKey: MDIHSTDASYVJAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-Chloromethyl-2-ethynyl-benzene 、 三甲基铝 在 二氯二茂锆 、 水 、 碘 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 4.5h， 以76%的产率得到(1E)-2-(2'-ethylphenyl)-1-iodopropene
  参考文献：
  名称：

  Zirconium-catalyzed methylalumination of heterosubstituted arylethynes: Factors affecting the regio-, stereo-, and chemoselectivities

  摘要：

  The Zr-catalyzed methylalumination of heterosubstituted arylethynes containing O, S, Cl, and Si can proceed in high yields (>70%) and in a highly regio-and stereoselective manner (>= 98-99%), although SO2Ph, Br, and Cl in a benzylic position present serious chemoselectivity-related problems. The low regioselectivity of 60% initially observed with o-ethynylphenol (1a) has been elevated to >= 98% through the use of either a catalytic amount of Zr(ebi)Cl-2 or Zr(2-Me-Ind)(2)Cl-2 or, more conveniently, the stoichiometric amount of ZrCp2Cl2, ZrCp2MeCl, or ZrCp2Me2 in conjunction with the use of a deficient amount (0.9 molar equiv.) of I-2 for subsequent iodinolysis. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.05.052
• 作为产物：
  描述：

  2-乙炔苯甲醇 在 氯化亚砜 作用下， 生成 1-Chloromethyl-2-ethynyl-benzene
  参考文献：
  名称：

  Synthesis and Solvolysis of o-, m-, and p-Ethynylbenzyl Chloride and Closely Related Structures. The Electronic Nature of the Acetylene Group¹

  摘要：

  DOI：

  10.1021/jo01346a032

文献信息

• Coating compositions, hydrophilic films, and hydrophilic film-coated articles
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：EP0857770B1

  公开（公告）日：2004-09-22
• Synthesis and Solvolysis of o-, m-, and p-Ethynylbenzyl Chloride and Closely Related Structures. The Electronic Nature of the Acetylene Group¹
  作者：John A. Landgrebe、Ronald H. Rynbrandt

  DOI：10.1021/jo01346a032

  日期：1966.8
• Zirconium-catalyzed methylalumination of heterosubstituted arylethynes: Factors affecting the regio-, stereo-, and chemoselectivities
  作者：Guangwei Wang、Gangguo Zhu、Ei-ichi Negishi

  DOI：10.1016/j.jorganchem.2007.05.052

  日期：2007.10

  The Zr-catalyzed methylalumination of heterosubstituted arylethynes containing O, S, Cl, and Si can proceed in high yields (>70%) and in a highly regio-and stereoselective manner (>= 98-99%), although SO2Ph, Br, and Cl in a benzylic position present serious chemoselectivity-related problems. The low regioselectivity of 60% initially observed with o-ethynylphenol (1a) has been elevated to >= 98% through the use of either a catalytic amount of Zr(ebi)Cl-2 or Zr(2-Me-Ind)(2)Cl-2 or, more conveniently, the stoichiometric amount of ZrCp2Cl2, ZrCp2MeCl, or ZrCp2Me2 in conjunction with the use of a deficient amount (0.9 molar equiv.) of I-2 for subsequent iodinolysis. (C) 2007 Elsevier B.V. All rights reserved.