1-(but-3-yn-1-yloxy)-2-iodobenzene | 155304-06-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(but-3-yn-1-yloxy)-2-iodobenzene
• 英文别名: 1-But-3-ynoxy-2-iodobenzene
• CAS: 155304-06-6
• 化学式: C₁₀H₉IO
• 分子量: 272.085
• InChiKey: GFMGXCGUIXUMTK-UHFFFAOYSA-N

物化性质

• 沸点：
  308.6±27.0 °C(Predicted)
• 密度：
  1.611±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(but-3-yn-1-yloxy)-2-iodobenzene 在 nickel dichloride chromium dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以52%的产率得到4-methylenechromane
  参考文献：
  名称：

  Chromium(II)-mediated nickel(II)-catalysed cyclisations of (iodoaryl)-substituted alkynes and alkynals

  摘要：

  The Chromium(II)-mediated Nickel(II)-catalysed cyclisations of (iodoaryl)-substituted alkynes 1, 2 and 7 and (iodoaryl)-substituted alkynals 9 and 10 to give the products 5, 6, 8, 11 and 12 respectively is described.

  DOI：

  10.1016/s0040-4039(00)76769-4
• 作为产物：
  描述：

  2-碘苯酚 、 对甲苯磺酸 3-丁炔酯 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以25%的产率得到1-(but-3-yn-1-yloxy)-2-iodobenzene
  参考文献：
  名称：

  Diastereoselective intramolecular SmI₂–H₂O–amine mediated couplings

  摘要：

  SmI2–H2O–胺混合物已被证明对分子内偶联反应有效，能在O-环己烯基碘苯酚衍生物偶联成杂环时提供高达100%的非对映选择性。

  DOI：

  10.1039/b305428d

文献信息

• Facile Construction of [6,6]-, [6,7]-, [6,8]-, and [6,9]Ring-Fused Triazole Frameworks by Copper-Catalyzed, Tandem, One-Pot, Click and Intramolecular Arylation Reactions: Elaboration to Fused Pentacyclic Derivatives
  作者：M. Nagarjuna Reddy、K. C. Kumara Swamy

  DOI：10.1002/ejoc.201101816

  日期：2012.4

  A sequential copper-catalyzed, one-pot, click reaction–intramolecular direct arylation, which involves two mechanistically distinct reactions (atom-economical click reaction and direct arylation of 1,2,3-triazole), to generate [6,6]-, [6,7]-, [6,8]-, and [6,9]ring-fused triazoles is reported. Furthermore, a unique divergence of reactivity between the fused triazoles prepared from 2-bromobenzyl azide

  连续铜催化、一锅、点击反应-分子内直接芳基化，涉及两个机械上不同的反应（原子经济点击反应和 1,2,3-三唑的直接芳基化），以生成 [6,6]- 、[6,7]-、[6,8]- 和 [6,9] 环稠合三唑被报道。此外，观察到由 2-溴苄基叠氮化物和 2-溴苯基叠氮化物制备的稠合三唑之间反应性的独特差异，导致前者形成稠合五环杂环，后者形成 C-C 偶联、联苯稠合三环产物在 Pd 催化下。所有关键产品均已通过单晶 X 射线晶体学表征。
• Synthesis of E- and Z-substituted methylene-3,4-dihydro-2H-1-benzopyrans by regio- and stereocontrolled palladium-catalyzed intramolecular cyclization
  作者：Olivier Barberan、Mouâd Alami、Jean-Daniel Brion

  DOI：10.1016/s0040-4039(01)00241-6

  日期：2001.4

  A stereocontrolled synthetic approach to E- and Z-substituted methylene-3,4-dihydro-2H-1-benzopyrans 5 is described from acyclic derivatives using as a key step the palladium-catalyzed intramolecular cyclic carbopalladation of iodoalkynes 4 followed by a carbonylation or a hydride ion capture process.

  从无环衍生物描述了E和Z取代的亚甲基-3,4-二氢-2 H -1-苯并吡喃5的立体控制合成方法，该方法使用钯催化的碘代炔烃4的分子内碳环缩合作为关键步骤，然后进行羰基化或氢化物离子捕获过程。
• Alkyne–azide cycloaddition catalyzed by a dinuclear copper(I) complex
  作者：Hong-Bin Chen、Nawodi Abeyrathna、Yi Liao

  DOI：10.1016/j.tetlet.2014.10.029

  日期：2014.11

  A novel dinuclear copper complex Cu-2(1)(pip)(2) was used as a catalyst for alkyne-azide cycloaddition (CuAAC) reaction. High yields (95-99%) were obtained for various substrates at a low loading of 0.2 mol %. The unique structure, high stability of the dinuclear structure in solution, and easy preparation make this complex not only a high-efficiency catalyst but also a model for understanding the mechanism of the CuAAC reaction. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of novel N-glycoside derivatives via CuSCN-catalyzed reactions and their SGLT2 inhibition activities
  作者：Shao-Tao Bai、De-Cai Xiong、Youhong Niu、Yan-Fen Wu、Xin-Shan Ye

  DOI：10.1016/j.tet.2015.05.108

  日期：2015.7

  A convenient approach to the synthesis of novel triazole-N-glycoside derivatives was developed via CuSCN-catalyzed click reaction and Ullmann-type coupling reaction for the first time. The SGLT2 inhibitory activities of these synthetic N-glycosides were evaluated, and some compounds showed moderate SGLT2 inhibition activities at 100 nM. The results could benefit the discovery of new SGLT2 inhibitors for the treatment of diabetes. (C) 2015 Elsevier Ltd. All rights reserved.
• Hodgson David M., Wells Christopher, Tetrahedron Lett, 35 (1994) N 10, S 1601-1604
  作者：Hodgson David M., Wells Christopher

  DOI：——

  日期：——