1,2,4-triphenylspiro[4,5]deca-1,3,7,9-tetraen-6-one | 1610359-50-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2,4-triphenylspiro[4,5]deca-1,3,7,9-tetraen-6-one
• 英文别名: 1,3,4-Triphenylspiro[4.5]deca-1,3,6,8-tetraen-10-one；1,3,4-triphenylspiro[4.5]deca-1,3,6,8-tetraen-10-one
• CAS: 1610359-50-6
• 化学式: C₂₈H₂₀O
• 分子量: 372.466
• InChiKey: HIKHIDGQQUUZJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-羟基二苯甲酮 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 73.0h， 生成 1,2,4-triphenylspiro[4,5]deca-1,3,7,9-tetraen-6-one
  参考文献：
  名称：

  Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes

  摘要：

  Appropriately substituted 2-alkenylphenols undergo a mild formal [3C+2C] cycloaddition with alkynes when treated with a Rh(III) catalyst and an oxidant. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety and the dearomatization of the phenol ring, provides a versatile and efficient approach to highly appealing spirocyclic skeletons and occurs with high selectivity.

  DOI：

  10.1021/ja5034952

文献信息

• Synthesis of Spirocyclic Enones by Rhodium-Catalyzed Dearomatizing Oxidative Annulation of 2-Alkenylphenols with Alkynes and Enynes
  作者：Szymon Kujawa、Daniel Best、David J. Burns、Hon Wai Lam

  DOI：10.1002/chem.201403454

  日期：2014.7.7

  The dearomatizing oxidative annulation of 2‐alkenylphenols with alkynes and enynes proceeds with high yields and regioselectivities under RhIII catalysis. These reactions are successful using Cu(OAc)2 or air as the stoichiometric oxidant, and provide spirocyclic enones, the basic ring system of which appears in several natural products. Application of this process to the preparation of a highly functionalized

  在Rh III催化下，2-炔基苯酚与炔烃和烯炔的脱芳烃氧化环化反应具有很高的收率和区域选择性。这些反应使用Cu（OAc）2或空气作为化学计量的氧化剂成功完成，并提供了螺环烯酮，其基本环系统出现在几种天然产物中。还证明了该方法在制备高度官能化的四环化合物中的应用。
• Nickel-Catalyzed Ring-Opening of Benzofurans for the Divergent Synthesis of <i>ortho</i>-Functionalized Phenol Derivatives
  作者：Changhui Lu、Yueping Lin、Minyan Wang、Jiaming Zhou、Shuo Wang、Huanfeng Jiang、Kai Kang、Liangbin Huang

  DOI：10.1021/acscatal.2c04442

  日期：2023.2.17

  The ring-opening reaction of benzofuran is a highly desirable, yet underdeveloped transformation for the construction of valuable phenol derivatives. Herein, we report a nickel-catalyzed ring-opening transformation of benzofuran with silanes, giving ortho-alkene-, branched/linear alkyl silane-, and alkenyl silane-substituted phenol derivatives selectively. Control experiments and DFT calculations supported

  苯并呋喃的开环反应是一种非常理想但尚未开发的转化，用于构建有价值的苯酚衍生物。在此，我们报道了镍催化的苯并呋喃与硅烷的开环转化，选择性地得到邻-烯烃-、支链/直链烷基硅烷-和烯基硅烷-取代的苯酚衍生物。对照实验和 DFT 计算支持 Ni-H 插入和 β-O 消除以实现苯并呋喃的正式 C-O 键活化，而不是通过将镍 (0) 直接氧化加成到苯并呋喃的 C-O 键中。通过 Ni(I)–H 或 Ni(I)–[Si] 中间体发生进一步的区域选择性氢化硅烷化或脱氢硅烷化，形成邻位-支链/直链烷基硅烷或烯基硅烷取代的苯酚衍生物。
• Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes
  作者：Andrés Seoane、Noelia Casanova、Noelia Quiñones、José L. Mascareñas、Moisés Gulías

  DOI：10.1021/ja5034952

  日期：2014.5.28

  Appropriately substituted 2-alkenylphenols undergo a mild formal [3C+2C] cycloaddition with alkynes when treated with a Rh(III) catalyst and an oxidant. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety and the dearomatization of the phenol ring, provides a versatile and efficient approach to highly appealing spirocyclic skeletons and occurs with high selectivity.