1-Phenyl-3-(tert-butoxy)-1-propyne

• 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-Phenyl-3-(tert-butoxy)-1-propyne
• 英文别名: 3-tert-butoxy-1-phenyl-1-propyne；(3-Tert-butoxy-1-propynyl)benzene；3-[(2-methylpropan-2-yl)oxy]prop-1-ynylbenzene
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: TZCNMQHDEPWQEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  甲基叔丁基醚 、 phenylethynyl trifluoromethyl sulfone 在 偶氮二异丁腈 作用下， 反应 2.0h， 以87%的产率得到1-Phenyl-3-(tert-butoxy)-1-propyne
  参考文献：
  名称：

  Alkynylation of C−H Bonds via Reaction with Acetylenic Triflones¹

  摘要：

  DOI：

  10.1021/ja953518p

文献信息

• A Simple and Powerful tert-Butylation of Carboxylic Acids and Alcohols
  作者：Kosuke Namba、Chie Ogasa、Kimika Kayano

  DOI：10.1055/a-2161-9689

  日期：2024.1

  A simple and safe tert-butylation reaction was developed. Treatment of various free amino acids with 1.1 equivalents of bis(trifluoromethanesulfonyl)imide in tert-butyl acetate directly afforded tert-butyl esters with free amino groups quickly and in good yields. In addition, various carboxylic acids and alcohols without amino groups were converted into tert-butyl esters and ethers, respectively, in

  开发了一种简单且安全的叔丁基化反应。用1.1当量的双(三氟甲磺酰基)亚胺的乙酸叔丁酯溶液处理各种游离氨基酸，可以快速且高收率地直接得到具有游离氨基的叔丁酯。此外，在少量催化量的双(三氟甲磺酰基)亚胺存在下，各种不含氨基的羧酸和醇分别以高产率转化为叔丁基酯和醚。与传统方法相比，游离氨基酸、羧酸和醇的所有叔丁基化反应进行得更快并且产率更高。
• Silver Ion-assisted Solvolysis of 2,2-Dibromo-1-phenylcyclopropanecarboxylic Acid: Solvent-dependent Competition between Decarboxylation and Ring Closure.
  作者：Leiv K. Sydnes、Rajesh Mungaroo、John S. Svendsen、Jacek Stawinski

  DOI：10.3891/acta.chem.scand.52-1392

  日期：——

  The solvolysis of the title compound has been studied in several alcohols (methanol, 2,2,2-trifluoroethanol, isopropyl alcohol, tert-butyl alcohol and 1,I,1,3,3,3-hexafluoro-2-propanol [HFP]) in the presence of an excess of sliver trifluoroacetate. In all solvents the corresponding butenolide, 4-bromo-3-phenyl-2(SH)-furanone, was a major or the predominant product. Another product formed in all solvents but HFP was (Z)-4-alkoxy-3-bromo-2-phenyl-2-butenoic acid, which resulted from solvent attack on intermediate allylic cations. Furthermore, both 3-alkoxy-1-phenyl-1-propyne and 3-alkoxy-1-phenyl-1-propanone were formed except when reactions were performed in HFP; their formation involved decarboxylation and their total yield was 15-40%.
• Synthesis of aryl- and vinylacetylene derivatives by copper-catalyzed reaction of aryl and vinyl iodides with terminal alkynes
  作者：Kazumi Okuro、Makoto Furuune、Masahiro Enna、Masahiro Miura、Masakatsu Nomura

  DOI：10.1021/jo00069a040

  日期：1993.8

  The coupling reaction of aryl iodides with terminal alkynes by using a catalyst system of CuI-PPhs in the presence of K2CO3 as base gives the corresponding arylated alkynes in excellent yields. Addition of PPh3 is essential for the reaction to proceed catalytically. Vinyl iodides also react smoothly with the alkynes to give enyne compounds with retention of the configurations. While DMF and DMSO can be used as solvents, DMSO is found to be effective for the reaction with aliphatic terminal alkynes. A reaction mechanism involving initial formation of copper acetylide species coordinated by PPh3 followed by reaction of aryl and vinyl iodides is proposed.
• A New Method of Synthesis for Propargylic Amines and Ethers via Benzotriazole Derivatives Using Sodium Dialkynyldiethylaluminates
  作者：Jin Hee Ahn、Meyoung Ju Joung、Nung Min Yoon、Daniela C. Oniciu、Alan R. Katritzky

  DOI：10.1021/jo9814750

  日期：1999.1.1

  1-(alpha-Aminoalkyl)benzotriazoles react with sodium dialkynyldiethylaluminates to give propargylic amines in excellent yields, including unsubstituted N,N-dialkyl propargylamines, which are difficult to obtain from Lithium acetylide. The reaction of alpha-benzotriazolyl alkyl ethers and sodium dialkynyldiethylaluminate in the presence of zinc iodide also gives propargylic ethers in excellent yields. Unsubstituted propargyl ethers are prepared via the desilylation of trimethylsilylpropargyl ethers.