1-(3,5-dimethoxyphenyl)-3-phenylprop-2-yn-1-ol | 1034136-14-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(3,5-dimethoxyphenyl)-3-phenylprop-2-yn-1-ol
• CAS: 1034136-14-5
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: RGDGRWCUWARBCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  443.2±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,5-dimethoxyphenyl)-3-phenylprop-2-yn-1-ol 在 caesium carbonate 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-(3,5-dimethoxybenzoyl)-1'-methyl-2-phenylspiro[cyclopent[2]ene-1,3'-indoline]-2',4-dione
  参考文献：
  名称：

  通过Aryne和Alkyne掺入制备环氧吲哚的螺环成环反应：取代了取代基的，无过渡金属的单罐方式进入螺旋螺并吲哚

  摘要：

  已经概念化并实施了“通过底物设计控制产品”策略，以利用芳烃和活化炔烃插入到羟吲哚中的潜力，以快速有效地在操作简单，单罐，过渡金属中提供药效学的茚满和环戊环化螺并吲哚支架。 -免费协议。

  DOI：

  10.1021/acs.orglett.7b01233
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 、 苯乙炔 在 Ti(2,3-dihydro-2,2-dimethyl-7-benzofuran-O)4 diethylzinc 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 24.0h， 以66%的产率得到1-(3,5-dimethoxyphenyl)-3-phenylprop-2-yn-1-ol
  参考文献：
  名称：

  Titanium and zirconium benzofuranoxides. Crystal structures and catalytic properties

  摘要：

  Ti(OiPr)4 或 Zr(OEt)4 与 4 当量的 2,3-二氢-2,2-二甲基-7-苯并呋喃醇 (ddbfoH) 在甲苯中反应生成中性配合物，这些配合物在固态时为 [Ti(μ-ddbfo)2(ddbfo)6] 和 [Zr(ddbfo)3(EtOH)(μ-EtO)]2 组成的二聚体。前者也可以通过 TiCl4 与 ddbfoH 的直接反应方便合成。这种耐空气的芳氧化合物被发现能够启动乳酸内酯的活性开环聚合，从而获得分子量分布窄的聚酯。同时，它还催化末端炔烃与芳基醛的加成反应。

  DOI：

  10.1039/b715048b

文献信息

• Diastereoselective Synthesis of Chromeno[3,2-<i>d</i>]isoxazoles via Brønsted Acid Catalyzed Tandem 1,6-Addition/Double Annulations of <i>o</i>-Hydroxyl Propargylic Alcohols
  作者：Zhu Li、Pei-Xu Zhang、Zhao-Zhao Li、Xing-Lu Zhang、Hong-Yuan Cao、Yu-Ning Gao、Ming Bian、Hui-Yu Chen、Zhen-Jiang Liu

  DOI：10.1021/acs.orglett.2c02830

  日期：2022.9.23

  A Brønsted acid catalyzed tandem process to access densely functionalized chromeno[3,2-d]isoxazoles with good to excellent yields and diastereoselectivities was disclosed. The procedure is proposed to involve a 1,6-conjugate addition/electrophilic addition/double annulations process of alkynyl o-quinone methides (o-AQMs) in situ generated from o-hydroxyl propargylic alcohols with nitrones. Mild conditions

  公开了一种布朗斯台德酸催化的串联工艺，用于获得致密官能化的铬烯基 [3,2- d ] 异恶唑，具有良好至优异的产率和非对映选择性。该程序拟涉及 1,6-共轭加成/亲电加成/双环化炔基邻苯二酚甲基化物 (o -AQMs) 的过程，原位由邻羟基炔丙醇和硝酮生成。温和的条件、良好的官能团相容性、易于放大反应和进一步的产品转化展示了其潜在的应用。
• Silver Trifluoromethanesulfonate-Catalyzed Annulation of Propargylic Alcohols with 3-Methyleneisoindolin-1-one
  作者：Xue-Song Li、Ya-Ping Han、Dan-tong Xu、Ming Li、Wan-Xu Wei、Yong-Min Liang

  DOI：10.1021/acs.joc.9b02533

  日期：2020.2.21

  A silver-catalyzed formal [3 + 3] annulation of 3-methyleneisoindolin-1-one with alkynol for the synthesis of 1,5-dihydroindolizin-3(2H)-one derivatives is disclosed. The protocol allows practical synthesis of N-heterocyclic scaffolds with a broad scope of functional groups and could be efficiently scaled up to gram scale, which incarnates a potential application of this methodology. In addition, a range of chlorine anion substitution of alkenes can be constructed by adjusting the structure of the alkynol substrates with the use of TMSCl.
• Tandem C-2 Functionalization–Intramolecular Azide–Alkyne 1,3-Dipolar Cycloaddition Reaction: A Convenient Route to Highly Diversified 9<i>H</i>-Benzo[<i>b</i>]pyrrolo[1,2-<i>g</i>][1,2,3]triazolo[1,5-<i>d</i>][1,4]diazepines
  作者：Mohd. Kamil Hussain、Mohd. Imran Ansari、Ruchir Kant、Kanchan Hajela

  DOI：10.1021/ol403420z

  日期：2014.1.17

  An efficient diversity-oriented synthetic approach to annulated 9H-benzo[b]pyrrolo[1,2-g][1,2,3]triazolo[1,5-d][1,4]diazepines has been developed using a R Sc(OTf)(3)-catalyzed two-component tandem C-2 functionalization intramolecular azide-alkyne 1,3-dipolar cycloaddition reaction. The reaction shows high substrate tolerance and provides a library of fused heterocycles that may. lead to novel biologically active compounds or drug lead molecules.
• One-Pot Synthesis of <i>N</i>-Fused Benzimidazo-β-carbolines through Sequential Propargylation/<i>aza</i>-Cycloisomerization Approach
  作者：Chada Raji Reddy、Karna Nair、Ejjirotu Srinivasu、Muppidi Subbarao、René Grée

  DOI：10.1021/acs.joc.3c02702

  日期：2024.2.16
• [EN] METHOD FOR IN-SITU FORMATION OF METATHESIS CATALYSTS<br/>[FR] PROCÉDÉ POUR LA FORMATION IN SITU DE CATALYSEURS DE MÉTATHÈSE
  申请人：SCHRODI YANN

  公开号：WO2011119778A2

  公开（公告）日：2011-09-29

  Synthetic methods for the in-situ formation of olefin metathesis catalysts are disclosed, as well as the use of such catalysts in metathesis reactions of olefins and olefin compounds. In one aspect, a method is provided for synthesizing an organometallic compound of the formula (I); comprising contacting a precursor compound of the formula (X1X2MLjL1kL3m)i with an acetylenic compound of the formula comprising a chelating moiety, optionally, in the presence of a neutral electron donor, wherein M is a Group 8 transition metal, L, L1, L2, and L3 are neutral electron donors, X1 and X2 are anionic ligands,j is 1, 2, or 3; k is zero, 1, or 2; m is zero or 1; n is 1 or 2; and i is an integer; with the proviso that k is zero when the precursor compound is contacted with the acetylenic compound in the presence of the neutral electron donor, and R1 and R2 are independently selected from hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, and functional groups, wherein R1 and R2 are linked and together form one or more cyclic groups, R2 and L2 are linked and together form one or more cyclic groups, and any other two or more of X1, X2, L1, L2, L3, R1, and R2 can be taken together to form one or more cyclic groups. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial and fine chemicals chemistry.