3-propyl-1H-isochromene | 26059-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-propyl-1H-isochromene
• 英文别名: 3-n-Propyl-1H-2-benzopyran
• CAS: 26059-44-9
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: MBRRXAFBJUWBGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-碘苄醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 [IrH(2-acetylphenyl)(acetone)(PPh₃)2]SbF₆ 三乙胺 作用下， 以 氯仿 为溶剂， 反应 7.0h， 生成 3-propyl-1H-isochromene
  参考文献：
  名称：

  氢化铱催化分子内炔烃加氢烷氧基化和加氢胺化反应。

  摘要：

  [反应：见正文]氢化铱（III）被证明是空气稳定的活性催化剂，用于分子内加氢烷氧基化和内部炔烃与近亲核试剂的加氢胺化反应。当区域选择性成为一个问题时，环化反应遵循高度选择性的6-endo-dig区域化学。

  DOI：

  10.1021/ol052186i

文献信息

• Triaryl-Like MONO-, BIS-, and TRISKITPHOS Phosphines: Synthesis, Solution NMR Studies, and a Comparison in Gold-Catalyzed Carbon–Heteroatom Bond Forming 5-<i>exo</i>-dig and 6-<i>endo</i>-dig Cyclizations
  作者：Simon Doherty、Julian G. Knight、Daniel O. Perry、Nicholas A. B. Ward、Dror M. Bittner、William McFarlane、Corinne Wills、Michael R. Probert

  DOI：10.1021/acs.organomet.6b00146

  日期：2016.5.9

  A homologous series of triaryl-like KITPHOS-type monophosphines containing one, two, or three bulky 12-phenyl-9,10-dihydro-9,10-ethenoanthracene (KITPHOS) units have been developed, and the influence of increasing steric bulk on their efficacy as ligands in gold(I)-catalyzed carbon-heteroatom bond-forming cyclizations has been investigated. Detailed solution NMR studies on Ph-TRISKITPHOS, its oxide, and the corresponding gold(I) chloride adduct identified a conformational exchange process involving a concerted librational motion of the individual anthracene-derived organic substituents about their P-C bonds. The cessation of this motion at reduced temperatures lowers the molecular symmetry such that the two C6H4 rings in each of the KITPHOS units become inequivalent; a lower energy process involving restricted rotation of the biaryl-like phenyl ring has also been identified. Electrophilic gold(I) complexes of these triaryl-like KITPHOS monophosphines catalyze the 5-exo-dig cycloisomerization of propargyl amides to afford the corresponding methylene oxazolines, which were used in a subsequent tandem carbonyl-ene reaction to afford functionalized 2 -substituted oxazolines. A comparative survey revealed that catalyst efficiency for cycloisomerization decreases in the order MONOKITPHOS = BISKITPHOS > PPh3 > TRISKITPHOS. The optimum system also catalyzes the selective 6-endo-dig cyclization of 2-alkynylbenzyl alcohols, 2-alkynylbenzoic acid, and 2-phenylethynyl benzamides; gratifyingly, in several cases the yields obtained are markedly higher and/or reaction times significantly shorter than those previously reported for related gold catalysts. Moreover, these are the first examples of gold(I)-catalyzed 6-endo-dig cycloisomerizations involving 2-phenylethynyl benzamides and, reassuringly, the optimum gold(I)/MONOKITPHOS systems either rivaled or outperformed existing silver or palladium based catalysts. The steric parameters of this homologous series of phosphines have been quantified and compared with selected triarylphosphines using a combination of Solid -G calculations, to determine the percentage of the metal coordination sphere shielded by the phosphine (the G parameter), and Salerno molecular buried volume calculations (SambVca) to determine the percent buried volume (%V-bur); the corresponding Tolman cone angles have also been determined from correlations.
• Isochromenes and their quinones through cyclisations with bisacetonitriledichloropalladium(II)
  作者：Robin G.F. Giles、Ivan R. Green、C.Peter Taylor

  DOI：10.1016/s0040-4039(99)00899-0

  日期：1999.6

  Bisacetonitriledichloropalladium(II) is found to cyclise ortho-alkenylbenzyl alcohols rapidly to the corresponding isochromenes. The reaction also proceeds rapidly for a 2-allyl-3-hydroxyalkyl-1,4-naphthoquinon when the product is a benzoisochromenequinone. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Gold-Catalyzed Benzylic CH Activation at Room Temperature
  作者：A. Stephen K. Hashmi、Sascha Schäfer、Michael Wölfle、Cesar Diez Gil、Peter Fischer、Antonio Laguna、M. Carmen Blanco、M. Concepción Gimeno

  DOI：10.1002/anie.200701521

  日期：2007.8.13
• Intramolecular Alkyne Hydroalkoxylation and Hydroamination Catalyzed by Iridium Hydrides
  作者：Xingwei Li、Anthony R. Chianese、Tiffany Vogel、Robert H. Crabtree

  DOI：10.1021/ol052186i

  日期：2005.11.1

  [reaction: see text] Iridium(III) hydrides prove to be air-stable active catalysts for intramolecular hydroalkoxylation and hydroamination of internal alkynes with proximate nucleophiles. The cyclization follows highly selective 6-endo-dig regiochemistry when regioselectivity is an issue.

  [反应：见正文]氢化铱（III）被证明是空气稳定的活性催化剂，用于分子内加氢烷氧基化和内部炔烃与近亲核试剂的加氢胺化反应。当区域选择性成为一个问题时，环化反应遵循高度选择性的6-endo-dig区域化学。