methyl (+/-)-2-(3-hydroxybut-1-yn-1-yl)benzoate | 152771-69-2

• 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: methyl (+/-)-2-(3-hydroxybut-1-yn-1-yl)benzoate
• 英文别名: methyl 2-(3-hydroxybut-1-yn-1-yl)benzoate；Methyl o-(3-hydroxy-1-butynyl)benzoate；methyl 2-(3-hydroxybut-1-ynyl)benzoate
• CAS: 152771-69-2
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: OZQRJGKBWOPJKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  341.3±27.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (+/-)-2-(3-hydroxybut-1-yn-1-yl)benzoate 在 potassium trimethylsilonate 、 氯甲酸甲酯 作用下， 以 乙醚 为溶剂， 反应 20.0h， 生成 o-(3-Hydroxy-1-butynyl)-α-diazoacetophenone
  参考文献：
  名称：

  A comparative study of the decomposition of o-alkynyl-substituted aryl diazo ketones. Synthesis of polysubstituted .beta.-naphthols via arylketene intermediates

  摘要：

  The photochemical, thermal, and rhodium-catalyzed decomposition reactions of several closely related o-alkynyl or o-alkenyl alpha-diazoaceto- and propiophenone derivatives have been studied. The reaction outcome is markedly dependent upon the reaction conditions employed for nitrogen extrusion. Thermolysis or photolysis of o-alkynyl alpha-diazopropiophenone derivatives yields polysubstituted beta-naphthols. These products are derived from Wolff rearrangement of the initially formed carbene to give an aryl ketene which undergoes intramolecular cyclization onto the o-alkynyl substituent. In direct contrast to the thermal and photochemical results, Rh(II)-catalyzed decomposition yields products derived from direct attack of a rhodium carbenoid onto the tethered pi-system producing a vinyl carbenoid intermediate. Further reaction of the cyclized carbenoid with the starting diazo compound furnishes a vinyl indenone which undergoes a rapid intramolecular Diels-Alder reaction to produce a novel dimer whose structure was elucidated by an X-ray crystal analysis. Replacement of the methyl group on the diazo center with a sterically less demanding hydrogen atom was also found to play an important role in controlling the outcome of the Rh(II)-catalyzed reaction.

  DOI：

  10.1021/jo00075a045
• 作为产物：
  描述：

  2-碘苯甲酸甲酯 、 3-丁炔-2-醇 在 copper(l) iodide 、 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 反应 10.0h， 以81%的产率得到methyl (+/-)-2-(3-hydroxybut-1-yn-1-yl)benzoate
  参考文献：
  名称：

  Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins

  摘要：

  一种范围广泛的磷酰基吲哚化合物通过一锅法从官能化丙炔醇和适当的P(III)前体经过碱介导的反应制备而成。该反应通过亚烯基磷氧化物的中间体进行。类似地，磷酰基异香豆素通过三氟乙酸介导的反应从亚烯基磷氧化物制备而成；后者也充当溶剂。有趣的是，在存在潮湿的三氟乙酸的情况下，除了磷酰基异香豆素外，还获得了无磷异香豆素。关键产品通过单晶X射线衍射进行了表征。

  DOI：

  10.3762/bjoc.10.99

文献信息

• [EN] ISOCHROMENE DERIVATIVES AS PHOSPHOINOSITIDE 3-KINASES INHIBITORS<br/>[FR] DÉRIVÉS D'ISOCHROMÈNE UTILES EN TANT QU'INHIBITEURS DES PHOSPHOINOSITIDE 3-KINASES
  申请人：CHIESI FARMA SPA

  公开号：WO2015091685A1

  公开（公告）日：2015-06-25

  The invention relates to compounds inhibiting phosphoinositide 3-kinases (PI3K), to pharmaceutical compositions comprising them and therapeutic use thereofin the treatment of disorders associated with PI3K enzymes.

  本发明涉及抑制磷脂酰肌醇3-激酶（PI3K）的化合物，包括含有它们的药物组合物以及它们在治疗与PI3K酶相关疾病的用途。
• ISOCHROMENE DERIVATIVES AS PHOSHOINOSITIDE 3-KINASES INHIBITORS
  申请人：CHIESI FARMACEUTICI S.p.A.

  公开号：US20150166549A1

  公开（公告）日：2015-06-18

  Compounds of formula (I) described herein are useful for inhibiting phosphoinositide 3-kinases (PI3K) and the treatment of disorders associated with PI3K enzymes.

  根据此处描述的公式(I)的化合物对于抑制磷脂酰肌醇3-激酶（PI3K）以及治疗与PI3K酶相关联的疾病是有用的。
• Cobalt-Catalyzed Reductive Coupling of Activated Alkenes with Alkynes
  作者：Hong-Tai Chang、Thiruvellore Thatai Jayanth、Chun-Chih Wang、Chien-Hong Cheng

  DOI：10.1021/ja073604c

  日期：2007.10.1

  Cobalt complex/Zn systems effectively catalyze the reductive coupling of activated alkenes with alkynes in the presence of water to give substituted alkenes with very high regio- and stereoselectivity in excellent yields. While the intermolecular reaction of acrylates, acrylonitriles, and vinyl sulfones with alkynes takes place in the presence of CoI2(PPh3)2/Zn, the reaction of enones and enals with

  钴络合物/锌系统在水存在下有效地催化活化烯烃与炔烃的还原偶联，以优异的产率得到具有非常高的区域选择性和立体选择性的取代烯烃。虽然丙烯酸酯、丙烯腈和乙烯基砜与炔烃的分子间反应发生在 CoI2(PPh3)2/Zn 存在下，但烯酮和烯醛与炔烃的反应需要使用 CoI2(dppe)/Zn/ZnI2 系统. 活化的烯烃（烯酮、烯醛、丙烯酸酯和丙烯腈）与炔烃的分子内还原偶联也有效。此外，使用该方法制备了多种环内酯和内酰胺。基于在 D2O 存在下进行的氘标记实验，提出了可能的机制途径。
• Synthesis of 4-Selanyl- and 4-Tellanyl-1<i>H</i>-isochromen-1-ones Promoted by Diorganyl Dichalcogenides and Oxone
  作者：Helen A. Goulart、José S. S. Neto、Angelita M. Barcellos、Krigor B. Silva、Maiara C. de Moraes、Raquel G. Jacob、Eder J. Lenardão、Thiago Barcellos、Gelson Perin

  DOI：10.1021/acs.joc.1c00271

  日期：2021.10.15

  A new method was developed for the synthesis of 4-chalcogenyl-1H-isochromen-1-ones through the 6-endo-dig electrophilic cyclization of 2-alkynylaryl esters and diorganyl dichalcogenides under ultrasound irradiation. The reactions were performed under mild conditions, using Oxone as a green oxidant to promote the cleavage of the chalcogen–chalcogen bond in diorganyl diselenides and ditellurides to generate

  开发了一种通过2-炔基芳基酯和二有机基二硫属元素化物在超声辐照下 6- endo - dig亲电环化反应合成 4-chalcogenyl- 1H - isochromen -ones的新方法。该反应在温和的条件下进行，使用 Oxone 作为绿色氧化剂来促进二有机二硒化物和二碲化物中硫属元素 - 硫属元素键的断裂，从而原位生成亲电子物质。30-70 分钟后，总共有 25 种化合物被选择性地获得，产率从良好到极好（74-95%）。该程序扩展到制备 5 H-硒酚[3,2 - c ] isochromen -5-ones。此外，首次将 4-chalcogenyl-1 H-isochromen-1-ones 被用作硫化反应中的底物，在无溶剂条件下使用劳森试剂和微波辐射，仅在 15 分钟内就以高达 99% 的产率获得了硫代衍生物。
• Regio- and Stereospecific Copper-Catalyzed Substitution Reaction of Propargylic Ammonium Salts with Aryl Grignard Reagents
  作者：Manuel Guisán-Ceinos、Victor Martín-Heras、Mariola Tortosa

  DOI：10.1021/jacs.7b05273

  日期：2017.6.28

  We have developed a copper-catalyzed substitution reaction of propargylic ammonium salts with aryl Grignard reagents. The reaction is stereospecific and α-regioselective and proceeds with exceptional functional group tolerance. Conveniently, a stable, inexpensive, and commercially available copper salt is used and no added ligand is required.

  我们已经开发了芳基格氏试剂与炔丙基铵盐的铜催化取代反应。该反应是立体特异性的和α-区域选择性的，并且以优异的官能团耐受性进行。方便地，使用稳定，便宜且可商购的铜盐，并且不需要添加的配体。