5,5'-dibutyl-3,3'-bisisoxazole | 100875-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5,5'-dibutyl-3,3'-bisisoxazole
• 英文别名: 5,5'-dibutyl-3,3'-biisoxazole；5,5'-dibutyl-[3,3']biisoxazolyl；5-Butyl-3-(5-butyl-1,2-oxazol-3-yl)-1,2-oxazole；5-butyl-3-(5-butyl-1,2-oxazol-3-yl)-1,2-oxazole
• CAS: 100875-78-3
• 化学式: C₁₄H₂₀N₂O₂
• 分子量: 248.325
• InChiKey: ZQXWQGTUPUHLGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  五羰基溴铼(I) 、 5,5'-dibutyl-3,3'-bisisoxazole 以 甲苯 为溶剂， 反应 3.0h， 以82%的产率得到[Re(CO)3(5,5'dibutyl-3,3'bisisoxazole)Br]
  参考文献：
  名称：

  A Click Chemistry Approach to 5,5′-Disubstituted-3,3′-Bisisoxazoles from Dichloroglyoxime and Alkynes: Luminescent Organometallic Iridium and Rhenium Bisisoxazole Complexes

  摘要：

  5,5'-Disubstituted-3,3'-bisisoxazoles are prepared in one step by the dropwise addition of aqueous potassium hydrogen carbonate to a mixture of dichloroglyoxime and terminal alkynes. The reaction exhibits a striking preference for the 5,5'-disubstituted 3,3'-bisisoxazole over the 4,5'-regioisomer. Organometallic iridium and rhenium bisisoxazole complexes are luminescent with emission wavelengths varying depending upon the identity of the 5,5'-substituent (phenyl, butyl).

  DOI：

  10.1021/jo4008755
• 作为产物：
  描述：

  1-己炔 、 二氯乙二肟 在 potassium hydrogencarbonate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 3.75h， 以77%的产率得到5,5'-dibutyl-3,3'-bisisoxazole
  参考文献：
  名称：

  A Click Chemistry Approach to 5,5′-Disubstituted-3,3′-Bisisoxazoles from Dichloroglyoxime and Alkynes: Luminescent Organometallic Iridium and Rhenium Bisisoxazole Complexes

  摘要：

  5,5'-Disubstituted-3,3'-bisisoxazoles are prepared in one step by the dropwise addition of aqueous potassium hydrogen carbonate to a mixture of dichloroglyoxime and terminal alkynes. The reaction exhibits a striking preference for the 5,5'-disubstituted 3,3'-bisisoxazole over the 4,5'-regioisomer. Organometallic iridium and rhenium bisisoxazole complexes are luminescent with emission wavelengths varying depending upon the identity of the 5,5'-substituent (phenyl, butyl).

  DOI：

  10.1021/jo4008755

文献信息

• Insights into the reaction paths of copper(i) acetylides with dichloroglyoxime leading to 3,3′-biisoxazoles
  作者：M. A. Topchiy、G. K. Sterligov、A. A. Ageshina、S. A. Rzhevskiy、L. I. Minaeva、M. S. Nechaev、A. F. Asachenko

  DOI：10.1007/s11172-022-3437-y

  日期：2022.3

  Base-free reaction of dichloroglyoxime with copper(i) acetylides gave 3,3′-biisoxazoles via a nucleophilic substitution of the chlorine atom of dichloroglyoxime with the acetylene moiety followed by cyclization of the intermediate formed. The effects of the solvent on the product yields were studied. In the case of substituted copper acetylides, 5,5′-disubstituted 3,3′-biisoxazoles were obtained in the yields from moderate to high and high regioselectivity.

  二氯乙二肟与铜(i)乙酰化物发生无碱反应，通过二氯乙二肟的氯原子与乙炔基团发生亲核取代反应，然后形成的中间体发生环化反应，生成 3,3′-双异噁唑。研究了溶剂对产物产量的影响。在取代铜乙酰化物的情况下，得到了 5,5′-二取代的 3,3′-联异噁唑，产率从中等到高不等，并且具有很高的区域选择性。
• Quilico et al., Gazzetta Chimica Italiana, 1957, vol. 87, p. 638,646
  作者：Quilico et al.

  DOI：——

  日期：——
• A Click Chemistry Approach to 5,5′-Disubstituted-3,3′-Bisisoxazoles from Dichloroglyoxime and Alkynes: Luminescent Organometallic Iridium and Rhenium Bisisoxazole Complexes
  作者：Phillip L. van der Peet、Timothy U. Connell、Christian Gunawan、Jonathan M. White、Paul S. Donnelly、Spencer J. Williams

  DOI：10.1021/jo4008755

  日期：2013.7.19

  5,5'-Disubstituted-3,3'-bisisoxazoles are prepared in one step by the dropwise addition of aqueous potassium hydrogen carbonate to a mixture of dichloroglyoxime and terminal alkynes. The reaction exhibits a striking preference for the 5,5'-disubstituted 3,3'-bisisoxazole over the 4,5'-regioisomer. Organometallic iridium and rhenium bisisoxazole complexes are luminescent with emission wavelengths varying depending upon the identity of the 5,5'-substituent (phenyl, butyl).