1-(2,6-dimethylphenyl)-3-phenylprop-2-yn-1-ol | 1184872-65-8

• 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-(2,6-dimethylphenyl)-3-phenylprop-2-yn-1-ol
• CAS: 1184872-65-8
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: CVQFOXMESVEBHE-UHFFFAOYSA-N

物化性质

• 沸点：
  398.5±42.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2,6-dimethylphenyl)-3-phenylprop-2-yn-1-ol 、 均三甲苯 在 gold(III) bromide 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 0.25h， 以81%的产率得到C₂₆H₂₆
  参考文献：
  名称：

  炔丙基醇和芳基亲核试剂的可调金催化反应

  摘要：

  研究了 1,3-二芳基炔丙醇与芳基亲核试剂的可调谐金 (III) 催化转化。通过适当的反应条件（时间、温度、催化剂、底物、亲核试剂、溶剂），开发了高选择性和可调节的合成方法，用于一锅形成三芳基-丙二烯、二芳基-茚或四芳基-烯丙基目标产物。在 NXS (X=Br, I) 的存在下，也以一锅法获得了适用于进一步 Pd 催化反应的相应 2-卤代茚。

  DOI：

  10.1002/open.202200030
• 作为产物：
  描述：

  苯基乙炔基三甲基硅烷 、 2,6-二甲基苯甲醛 在 P(PhCH₂NCH₂CH₂)3N 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以96%的产率得到1-(2,6-dimethylphenyl)-3-phenylprop-2-yn-1-ol
  参考文献：
  名称：

  P(PhCH₂NCH₂CH₂)₃N: An Efficient Lewis Base Catalyst for the Synthesis of Propargylic Alcohols and Morita−Baylis−Hillman Adducts via Aldehyde Alkynylation

  摘要：

  Proazaphosphatrane P(PhCH2NCH2CH2)(3)N (1a) is an efficient catalyst for the addition of aryl trimethylsilyl alkynes to a variety of aromatic, aliphatic, and heterocyclic aldehydes in THF at room temperature. The reaction conditions are mild and employ a low catalyst loading (ca. 5 mol %). Only propargylic alcohols were isolated in good to excellent isolated yields when electron-rich, electron-neutral, heterocyclic, and aliphatic aldehydes were employed, whereas beta-branched Morita-Baylis-Hillman (MBH) type adducts were isolated with electron-deficient aromatic aldehydes after conventional acid hydrolysis of the TMS ether products. Alkynes containing heterocyclic and aromatic groups bearing electron-withdrawing or -donating substituents underwent clean addition to cyclohexanecarboxaldehyde and to electron-rich aromatic aldehydes to give propargylic alcohols in excellent isolated yields. beta-Branched Morita-Baylis-Hillman (MBH) type adducts were isolated when electron-deficient aromatic aldehydes were employed. Reaction pathways to both types of products are proposed.

  DOI：

  10.1021/jo9012332

文献信息

• Visible Light-Induced Reductive Alkynylation of Aldehydes by Umpolung Approach
  作者：Ibuki Tanaka、Masaya Sawamura、Yohei Shimizu

  DOI：10.1021/acs.orglett.1c03927

  日期：2022.1.21

  irradiation. Ketyl radicals, generated by single-electron reduction of aldehydes through proton-coupled electron transfer (PCET), reacted with electrophilic alkynylsulfones. Sterically demanding bulky aldehydes reacted smoothly under the Umpolung reaction conditions. Moreover, the alkynylation proceeded chemoselectively with an aryl aldehyde group in the presence of other carbonyl groups including an aliphatic

  通过 Umpolung 方法对醛进行还原性炔基化是在蓝色 LED 照射下使用光氧化还原催化剂开发的。通过质子耦合电子转移 (PCET) 醛的单电子还原产生的酮基自由基与亲电子炔基砜反应。空间要求高的大体积醛在 Umpolung 反应条件下反应平稳。此外，在包括脂肪族醛基在内的其他羰基存在下，炔基化与芳基醛基化学选择性地进行。
• Regio- and Diastereoselective Radical Dimerization Reactions for the Construction of Benzo[<i>f</i>]isoindole Dimers
  作者：Chuanchuan Wang、Jingyi Lin、Haiyang Huang、Changqing Ye、Hongli Bao

  DOI：10.1021/acs.orglett.4c00587

  日期：2024.4.5

  This study presents a novel approach for synthesizing benzo[f]isoindole dimers, which involves cascade cyclization and oxidative radical dimerization. Our method allows for the formation of up to five carbon–carbon bonds in a single reaction, exhibiting remarkable diastereoselectivity and regioselectivity. The mechanism and regioselectivity were investigated through a combination of experiments and

  本研究提出了一种合成苯并[ f ]异吲哚二聚体的新方法，涉及级联环化和氧化自由基二聚化。我们的方法允许在单个反应中形成多达五个碳-碳键，表现出显着的非对映选择性和区域选择性。通过实验和计算相结合的方式研究了其机理和区域选择性。
• P(PhCH₂NCH₂CH₂)₃N: An Efficient Lewis Base Catalyst for the Synthesis of Propargylic Alcohols and Morita−Baylis−Hillman Adducts via Aldehyde Alkynylation
  作者：Kuldeep Wadhwa、Venkat Reddy Chintareddy、John G. Verkade

  DOI：10.1021/jo9012332

  日期：2009.9.4

  Proazaphosphatrane P(PhCH2NCH2CH2)(3)N (1a) is an efficient catalyst for the addition of aryl trimethylsilyl alkynes to a variety of aromatic, aliphatic, and heterocyclic aldehydes in THF at room temperature. The reaction conditions are mild and employ a low catalyst loading (ca. 5 mol %). Only propargylic alcohols were isolated in good to excellent isolated yields when electron-rich, electron-neutral, heterocyclic, and aliphatic aldehydes were employed, whereas beta-branched Morita-Baylis-Hillman (MBH) type adducts were isolated with electron-deficient aromatic aldehydes after conventional acid hydrolysis of the TMS ether products. Alkynes containing heterocyclic and aromatic groups bearing electron-withdrawing or -donating substituents underwent clean addition to cyclohexanecarboxaldehyde and to electron-rich aromatic aldehydes to give propargylic alcohols in excellent isolated yields. beta-Branched Morita-Baylis-Hillman (MBH) type adducts were isolated when electron-deficient aromatic aldehydes were employed. Reaction pathways to both types of products are proposed.
• Tunable Gold‐catalyzed Reactions of Propargyl Alcohols and Aryl Nucleophiles
  作者：Helgi Freyr Jónsson、Thomas Nordbø Solvi、Sondre Lomeland、Ann Christin Reiersølmoen、Anne Fiksdahl

  DOI：10.1002/open.202200030

  日期：2022.5

  alcohols with aryl nucleophiles were studied. Highly selective and tunable synthetic methods were developed for one-pot formation of either triaryl-allenes, diaryl-indenes or tetraaryl-allyl target products by appropriate reaction conditions (time, temperature, catalyst, substrate, nucleophile, solvent). Corresponding 2-halo-indenes, appropriate for further Pd-catalyzed reactions, were also obtained

  研究了 1,3-二芳基炔丙醇与芳基亲核试剂的可调谐金 (III) 催化转化。通过适当的反应条件（时间、温度、催化剂、底物、亲核试剂、溶剂），开发了高选择性和可调节的合成方法，用于一锅形成三芳基-丙二烯、二芳基-茚或四芳基-烯丙基目标产物。在 NXS (X=Br, I) 的存在下，也以一锅法获得了适用于进一步 Pd 催化反应的相应 2-卤代茚。