2-(3-methoxyphenyl)but-3-yn-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-methoxyphenyl)but-3-yn-2-ol
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: VWGIQOFAUAAUGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyphenyl)but-3-yn-2-ol 在 硫酸 、 mercury(II) oxide 作用下， 生成 3-hydroxy-3-(3-methoxyphenyl)butan-2-one
  参考文献：
  名称：

  Analogues of Acifran:  Agonists of the High and Low Affinity Niacin Receptors, GPR109a and GPR109b

  摘要：

  Recently identified GPCRs, GPR109a and GPR109b, the high and low affinity receptors for niacin, may represent good targets for the development of HDL elevating drugs for the treatment of atherosclerosis. Acifran, an agonist of both receptors, has been tested in human subjects, yet until recently very few analogs had been reported. We describe a series of acifran analogs prepared using newly developed synthetic pathways and evaluated as agonists for GPR109a and GPR109b, resulting in identification of compounds with improved activity at these receptors.

  DOI：

  10.1021/jm070022x
• 作为产物：
  描述：

  在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以3.99 g的产率得到2-(3-methoxyphenyl)but-3-yn-2-ol
  参考文献：
  名称：

  碳阳离子的配位诱导立体控制：外消旋叔醇的不对称还原脱氧

  摘要：

  引发对碳正离子的面部控制的固有困难限制了它们作为不对称催化中间体的效用。我们现在已经表明，涉及底物与手性过渡金属催化剂的可逆配位的对接策略可用于实现对中间叔碳正离子的高度立体选择性亲核攻击。这种方法已被实施以实现叔醇的对映选择性还原脱氧的第一个例子。通过应用新型 Hantzsch 酯类似物作为方便的氢化物来源，这种还原具有高对映性（高达 96% ee）和区域选择性（高达 >50:1 rr）。深入的机理研究支持通过关键的丙二烯部分与铱金属中心配位的叔碳正离子的参与。

  DOI：

  10.1021/jacs.9b00862

文献信息

• Platinum Catalysed Hydrostannylation of Terminal Alkynes; Highly Selective Synthesis of Vinyl Stannanes
  作者：Dean D. Roberts、Mark G. McLaughlin

  DOI：10.1002/adsc.202300379

  日期：2023.5.23

  β-(E)-vinyl stannane. The catalyst system is able to provide the corresponding vinyl stannane in selectivities which surpasses that which is typically afforded under palladium catalysis. Additionally, a telescoped hydrometallation/cross-coupling sequence has been developed, allowing for application of the vinyl stannanes without excessive manipulation or purification of the intermediate stannane.

  我们首次研究了铂络合物在末端炔烃氢化锡基化中的应用。筛选了一系列铂络合物，事实证明 PtCl 2 /XPhos 为 β-(E)-乙烯基锡烷提供了最佳选择性。该催化剂体系能够以超过通常在钯催化下提供的选择性提供相应的乙烯基锡烷。此外，还开发了一种伸缩式加氢金属化/交叉偶联序列，允许在不过度操作或纯化中间体锡烷的情况下应用乙烯基锡烷。
• Radical Hydro-Fluorosulfonylation of Propargylic Alcohols via Electron Donor–Acceptor Photoactivation
  作者：Yingyin Zhang、Qingyuan Feng、Yu Zheng、Yanju Lu、Saihu Liao、Shenlin Huang

  DOI：10.1021/acs.orglett.4c00010

  日期：2024.2.23

  photoactivation of the electron donor–acceptor (EDA) complex. The reaction avoids the requirement for photocatalysts, bases, hydrogen donor reagents, any other additives, and harsh conditions, enabling the facile synthesis of various functionalized γ-hydroxy (E)-alkenylsulfonyl fluorides. These multifunctional sulfonyl fluorides can be further diversified, providing access to various privileged molecules

  基于电子供体-受体 (EDA) 复合物的光活化，提出了使用 FSO 2 Cl 进行炔丙醇的自由基氢氟磺酰化。该反应不需要光催化剂、碱、供氢试剂、任何其他添加剂和苛刻的条件，从而能够轻松合成各种官能化的γ-羟基( E )-烯基磺酰氟。这些多功能磺酰氟可以进一步多样化，提供各种具有生物相关性的特殊分子。
• Rh(III)-Catalyzed [4 + 1] Annulation of Benzamides with Vinyl Cyclic Carbonates for the Synthesis of Isoindolinones
  作者：Xiang Li、Hang Cheng、Jianghao Shao、Guodong Zhang、Shuilong Zhang

  DOI：10.1021/acs.orglett.3c03899

  日期：2024.2.23

  A Rh(III)-catalyzed C–H bond activation and subsequent [4+1] annulation of benzamides with vinyl cyclic carbonates have been developed for the synthesis of isoindolinones, in which the electron-rich alkenes could serve as one-carbon units. This reaction proceeds smoothly with high regioselectivity under oxidant- and silver-free conditions and exhibits broad substrate scope and functional group tolerance

  Rh(III) 催化的 C-H 键活化和随后苯甲酰胺与乙烯基环状碳酸酯的 [4+1] 环化已被开发用于合成异吲哚啉酮，其中富电子的烯烃可以作为一碳单元。该反应在无氧化剂和无银条件下以高区域选择性顺利进行，并表现出广泛的底物范围和官能团耐受性，包括一些生物活性材料。产品的放大反应和衍生化进一步证明了这种转化的潜在合成效用。
• Improved synthesis of tertiary propargyl alcohols by the Favorskii reaction of alkyl aryl (hetaryl) ketones with acetylene
  作者：E. Yu. Shmidt、I. A. Bidusenko、N. I. Protsuk、A. I. Mikhaleva、B. A. Trofimov

  DOI：10.1134/s1070428013010028

  日期：2013.1

  Alkyl aryl (hetaryl) ketones react with acetylene under atmospheric pressure in the superbasic system KOH-EtOH-H2O-DMSO at 10-15A degrees C (2 h) to give the corresponding tertiary propargyl alcohols in up to 91% yield. The procedure requires no large excess of KOH and low-boiling inflammable solvents, produces few wastes, and is safe and convenient on the laboratory scale; there are no limitations for its large-scale application. DOI: 10.1134/S1070428013010028
• A peculiar transition-metal-free cyclodimerization of propargylic alcohols to vinyl bicyclic ketals
  作者：Boris A. Trofimov、Elena Yu. Schmidt、Ivan A. Bidusenko、Igor’ A. Ushakov、Nadezhda I. Protsuk、Nadezhda V. Zorina、Albina I. Mikhaleva

  DOI：10.1016/j.tet.2011.11.050

  日期：2012.1

  Propargylic alcohols, alkylaryl(hetaryl)ethynyl carbinols, under transition-metal-free conditions (KOH/DMSO, 70-80 degrees C, 10-15 min) unexpectedly undergo stereoselective cyclodimerization to 7-methylene-6,8-dioxabicyclo[3.2.1]octanes having the scaffold of known insect pheromones and marine toxins. Under acetylenic pressure the yields of bicyclic ketals reach 80%. In all the cases, the cyclodimers are formed exclusively as one diastereomer. (C) 2011 Elsevier Ltd. All rights reserved.