ethyl 4-hydroxy-4,4-diphenylbut-2-ynoate | 202350-95-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 4-hydroxy-4,4-diphenylbut-2-ynoate
• CAS: 202350-95-6
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: JCAOWQZVTBVSDX-UHFFFAOYSA-N

物化性质

• 沸点：
  461.7±45.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-4,4-diphenylbut-2-ynoate 在 4-二甲氨基吡啶 、 cis-dichlorobis(triphenylphosphine)platinum(II) 、 亚碘酰苯 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Pt-Catalyzed Pentannulations from In Situ Generated Metallo−Carbenoids Utilizing Propargylic Esters

  摘要：

  A highly selective and efficient Pt-catalyzed pentannulation reaction beginning from propargylic esters is described. The key to this reaction is the use of a PtCl2(PPh3)2/PhIO catalyst combination that allows the in situ generation of Pt-carbenoid intermediates, which lead to good yields (61-84%) of the desired pentannulated compounds.

  DOI：

  10.1021/ja053192c
• 作为产物：
  描述：

  4,4,4-triethoxy-1,1-diphenylbut-2-yn-1-ol 生成 ethyl 4-hydroxy-4,4-diphenylbut-2-ynoate
  参考文献：
  名称：

  BOCHE, G.;BIGALKE, J., TETRAHEDRON LETT., 1984, 25, N 9, 955-958

  摘要：

  DOI：

文献信息

• Cobalt‐Catalyzed Regioselective [4+2] Annulation/Lactonization of Benzamides with 4‐Hydroxy‐2‐Alkynoates under Aerobic Conditions
  作者：Nachimuthu Muniraj、Anil Kumar、Kandikere Ramaiah Prabhu

  DOI：10.1002/adsc.201901119

  日期：2020.1.7

  A cobalt‐catalyzed regioselective [4+2] annulation/lactonization reaction of benzamides with 4‐hydroxy‐2‐alkynoates is reported. This reaction utilizes air as an oxidant rather than metal salts. The method is operationally simple, mild, and sustainable. This protocol exhibits a broad substrate scope and compatible with a variety of functional groups furnishing the corresponding 1,4‐dihydrofuro[3,4‐c]isoquinoline‐3

  据报道，苯甲酰胺与4-羟基-2-链烷酸酯发生钴催化的区域选择性[4 + 2]环化/内酯化反应。该反应利用空气而不是金属盐作为氧化剂。该方法操作简单，温和且可持续。该方案具有广泛的底物范围，并与提供相应的1,4-二氢呋喃[3,4- c ]异喹啉-3,5-二酮衍生物的各种官能团兼容，具有良好的产率和较高的区域选择性。
• Reactions of alkyl 4-hydroxybut-2-ynoates with arenes under superelectrophilic activation with triflic acid or HUSY zeolite: Alternative propargylation or allenylation of arenes, and synthesis of furan-2-ones
  作者：Natalia A. Devleshova、Stanislav V. Lozovskiy、Aleksander V. Vasilyev

  DOI：10.1016/j.tet.2019.130517

  日期：2019.9

  respectively. Reactions of these species with arenes at C4 lead to products of arene propargylation, alternatively, reactions at C2 result in allenylation of arenes, followed by further transformation into furan-2-ones. Using quantum chemical calculations by the DFT method, it has been shown that the reactivity of such propargyl-allenyl cations is mainly explained by orbital factors. Plausible reaction mechanism

  烷基-4-芳基的反应（或4,4-二芳基）-4-羟基丁-2- ynOAtes [氩（H或Ar'）（OH）C 4 -C 3 ≡C 2 -CO 2 ALK]与芳烃下三氟甲基磺酸TfOH或HUSY沸石的作用导致形成两种主要化合物：芳基取代的呋喃-2-酮或富电子芳烃的炔丙基化产物。在这些转换键的反应性中间体相应的起始butynOAtes中，Ar（H或Ar'）（的O，O-双质子形式+ OH 2）C 4 -C 3 ≡C 2 - C（= O + H）（OAlk） ，其脱水会产生介晶的炔丙基-烯丙基阳离子Ar（H或Ar'）（OH）4 C+ -C 3 ≡C 2 -C（= O + H）（OAlk）↔的Ar（H或Ar'）（OH） 4 C = C 3  =  2 Ç + -C（= O + H）（OAlk），在碳C4和C2上分别具有两个亲电中心。这些物质与芳烃在C4的反应会导致芳烃的炔丙基化产物，或者，在C2的反应会
• Manganese‐Catalysed C−H Activation: A Regioselective C−H Alkenylation of Indoles and other (hetero)aromatics with 4‐Hydroxy‐2‐Alkynoates Leading to Concomitant Lactonization
  作者：Anil Kumar、Nachimuthu Muniraj、Kandikere Ramaiah Prabhu

  DOI：10.1002/adsc.201900678

  日期：2019.11.5

  A manganese‐catalyzed C−H bond alkenylation of indoles at C2‐position with 4‐hydroxy‐2‐alkynoates leading to concomitant lactonization under removable directing group strategy has been disclosed. This lactonization strategy exhibits regioselectivity, a broad substrate scope, and a good functional group tolerance furnishing the products in low to high yields. The regioselectivity is guided by the electronic

  已经公开了锰在4-位-2-羟基的链烷酸酯在C2-位的吲哚的锰催化的CH键链烯基化，从而在可移动的导向基团策略下导致伴随的内酯化。这种内酯化策略显示出区域选择性，广泛的底物范围和良好的官能团耐受性，从而以低到高收率提供了产品。区域选择性受酯基团的电子效应以及4-羟基-2-链烷酸酯的C4位的空间体积的影响。反应后，直接除去了导向基团以获得不含NH的吲哚。
• Regioselective annulation of propargyl alcohols with ambident-enols: A Ca(II)-catalyzed trisubstituted benzochromene synthesis
  作者：Srinivasarao Yaragorla、Abhishek Pareek、Ravikrishna Dada

  DOI：10.1016/j.tetlet.2017.10.077

  日期：2017.12

  cyclization between propargyl alcohols and ambident enols such as naphthols, 4-hydroxy coumarin, cyclohexane-1,3-dione, 5,5-dimethylcyclohexane-1,3-dione is described using Ca(OTf)2 under solvent free conditions. The reaction proceeds through a cascade annulation which involves an etherification, Claisen type rearrangement, allene formation and endocyclization. Further, we extended this method to the synthesis

  使用Ca（OTf）2在以下条件下描述了炔丙醇与环境烯醇（例如萘酚，4-羟基香豆素，环己烷-1,3-二酮，5,5-二甲基环己烷-1,3-二酮）之间的高度区域选择性，6-内环化。无溶剂条件。反应通过级联反应进行，该级联反应涉及醚化，克莱森（Claisen）型重排，丙二烯形成和内环化。此外，我们将该方法扩展到碘衍生物的合成，并证明了交叉偶联反应的反应性。
• Rhodium(III)-Catalyzed C–H Activation: A Cascade Approach for the Regioselective Synthesis of Fused Heterocyclic Lactone Scaffolds
  作者：Anil Kumar、Kandikere Ramaiah Prabhu

  DOI：10.1021/acs.joc.9b03266

  日期：2020.3.6

  A Rh(III)-catalyzed cascade C-H activation; regioselective [4 + 2] oxidative annulation; and lactonization of aromatic acids, anhydrides, and acrylic acid derivatives with 4-hydroxy-2-alkynoates have been disclosed. This strategy leads to fused heterocyclic lactone scaffolds in a single step with moderate functional group tolerance and excellent site selectivity. Besides, in one step, an antipode of

  Rh（III）催化的级联CH活化；区域选择性[4 + 2]氧化环化；已经公开了芳族酸，酸酐和丙烯酸衍生物与4-羟基-2-链烷酸酯的内酯化反应。这种策略可以一步合成具有稠合的杂环内酯支架，具有中等的官能团耐受性和出色的位点选择性。此外，一步合成了含有三环异香豆素骨架的头孢菌中间体天然产物的对映体。