2-(4-chlorobenzyl)-4,5-dihydrothiazole

• 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: 2-(4-chlorobenzyl)-4,5-dihydrothiazole
• 英文别名: 2-[(4-Chlorophenyl)methyl]-4,5-dihydrothiazole；2-[(4-chlorophenyl)methyl]-4,5-dihydro-1,3-thiazole
• 化学式: C₁₀H₁₀ClNS
• 分子量: 211.715
• InChiKey: QSWUAJVHQRYCPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chlorobenzyl)-4,5-dihydrothiazole 在 copper(l) iodide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以45%的产率得到2-(4-氯苯甲酰基)噻唑
  参考文献：
  名称：

  DDQ诱导杂环的脱氢对C ？C双键形成：2-噻唑和2-恶唑的合成

  摘要：

  像牛一样强： 2-噻唑和2-恶唑是通过2-噻唑啉和2-恶唑啉的氧化反应形成的，不需要在C4和C5位置处有取代基。DDQ在此转化过程中起氧化剂的作用，并且不需要金属。该通用步骤显示出良好的官能团耐受性，并以中等至极好的收率提供了各种2-噻唑和2-恶唑。

  DOI：

  10.1002/asia.201300267
• 作为产物：
  描述：

  巯基乙胺 、 对氯苯乙腈 以 乙醇 为溶剂， 以88%的产率得到2-(4-chlorobenzyl)-4,5-dihydrothiazole
  参考文献：
  名称：

  Synthèse, activités anti-parasitaire et anti-fongique d'arylalkyl- et d'arylvinylthiazolines

  摘要：

  Twenty-seven arylalkyl- or arylvinylthiazolines were synthesized and tested in vitro against three genera of nematodes, various yeasts and opportunistic fungi. Vinyl compounds seem to have an interesting filaricidal activity against Molinema dessetae and anti-fungal activity against yeasts.

  DOI：

  10.1016/0223-5234(93)90076-q

文献信息

• A one step synthesis of thiazolines from esters
  作者：Carl A. Busacca、Yong Dong、Earl M. Spinelli

  DOI：10.1016/0040-4039(96)00451-0

  日期：1996.4

  Condensation of the triisobutylaluminum complex of cysteamine HCl with a variety of carboxylic esters furnishes thiazolines in one step. This new method has been applied to chiral α-aminoesters to give α-amino thiazolines of high optical purity, yet N-benzyl protection of the amine is required.

  半胱胺盐酸盐的三异丁基铝络合物与多种羧酸酯的缩合一步即可提供噻唑啉。该新方法已应用于手性α-氨基酯，以得到高光学纯度的α-氨基噻唑啉，但仍需要胺的N-苄基保护。
• Solvent-Free Tandem Synthesis of 2-Thiazolines and 2-Oxazolines Catalyzed by a Copper Catalyst
  作者：Xiangnan Li、Baoyue Zhou、Jin Zhang、Mengyao She、Shujuan An、Haixia Ge、Cong Li、Bing Yin、Jianli Li、Zhen Shi

  DOI：10.1002/ejoc.201101786

  日期：2012.3

  Tandem reactions of nitriles with 2-aminoethanethiol hydrochloride or amino alcohols in the presence of a catalytic amount of cupric methacrylate (CuII2L4, L = methacrylate) were employed to prepare 2-thiazolines and 2-oxazolines under mild reaction conditions. The synthetic procedure showed high selectivity for the synthesis of mono- and bis-thiazolines and oxazolines, and a variety of 2-thiazolines

  在催化量的甲基丙烯酸铜（CuII2L4，L = 甲基丙烯酸酯）存在下，腈与 2-氨基乙硫醇盐酸盐或氨基醇的串联反应用于在温和的反应条件下制备 2-噻唑啉和 2-恶唑啉。该合成方法对单和双噻唑啉和恶唑啉的合成显示出高选择性，并且以良好到极好的收率获得了多种 2-噻唑啉和 2-恶唑啉。
• A straightforward metal-free synthesis of 2-substituted thiazolines in air
  作者：Michael Trose、Faïma Lazreg、Mathieu Lesieur、Catherine S. J. Cazin

  DOI：10.1039/c5gc00286a

  日期：——

  A range of 2-substituted 4,5-dihydrothiazoles was easily synthesised from the reaction of nitriles with cysteamine in the presence of a catalytic amount of NaOH.

  一系列2-取代的4,5-二氢噻唑易于在催化剂量的NaOH存在下，通过腈与半胱氨酸的反应合成。
• DDQ-Induced Dehydrogenation of Heterocycles for CC Double Bond Formation: Synthesis of 2-Thiazoles and 2-Oxazoles
  作者：Xiangnan Li、Cheng Li、Bing Yin、Cong Li、Ping Liu、Jianli Li、Zhen Shi

  DOI：10.1002/asia.201300267

  日期：2013.7

  Strong as an Ox: 2‐Thiazoles and 2‐oxazoles are formed by oxidation of 2‐thiazolines and 2‐oxazolines without requiring substituents at the C4 and C5 positions. DDQ plays an important role as the oxidant in this transformation and metal is unnecessary. This general procedure shows good functional group tolerance and provides a wide variety of 2‐thiazoles and 2‐oxazoles in moderate to excellent yields

  像牛一样强： 2-噻唑和2-恶唑是通过2-噻唑啉和2-恶唑啉的氧化反应形成的，不需要在C4和C5位置处有取代基。DDQ在此转化过程中起氧化剂的作用，并且不需要金属。该通用步骤显示出良好的官能团耐受性，并以中等至极好的收率提供了各种2-噻唑和2-恶唑。
• Synthèse, activités anti-parasitaire et anti-fongique d'arylalkyl- et d'arylvinylthiazolines
  作者：R Caujolle、G Baziard-Mouysset、JD Favrot、M Payard、PR Loiseau、H Amarouch、MD Linas、JP Seguela、PM Loiseau、C Bories、P Gayral

  DOI：10.1016/0223-5234(93)90076-q

  日期：1993.1

  Twenty-seven arylalkyl- or arylvinylthiazolines were synthesized and tested in vitro against three genera of nematodes, various yeasts and opportunistic fungi. Vinyl compounds seem to have an interesting filaricidal activity against Molinema dessetae and anti-fungal activity against yeasts.