2-(1-phenylvinyl)phenol-d2 | 39477-89-9

• 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: 2-(1-phenylvinyl)phenol-d2
• 英文别名: 2-(1-phenylvinyl-2,2-d₂)phenol
• CAS: 39477-89-9
• 化学式: C₁₄H₁₂O
• 分子量: 198.233
• InChiKey: QYPBOXRMLFPDEQ-DICFDUPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 2-(1-phenylvinyl)phenol-d2 在 carbonyl(pentamethylcyclopentadienyl)cobalt diiodide 、 copper(II) acetate monohydrate 、 silver carbonate 作用下， 以 邻二甲苯 为溶剂， 反应 0.33h， 生成 4-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  Cp*Co(III)-Catalyzed Annulations of 2-Alkenylphenols with CO: Mild Access to Coumarin Derivatives

  摘要：

  Cp*Co(III)-catalyzed annulations of 2-alkenylphenols with CO for the synthesis of coumarin derivatives have been developed. The reaction features mild reaction conditions, broad substrate scope, and good functional group tolerance. Preliminary mechanistic studies were conducted, suggesting that C-H activation is the turnover limiting step. Furthermore, the efficiency of this reaction was demonstrated by the rapid total synthesis of three natural products herniarin, xanthyletin, and seselin.

  DOI：

  10.1021/acs.orglett.5b02728
• 作为产物：
  描述：

  2-(1-苯基乙烯基)苯酚 在 重水 、 sodium acetate 、 palladium diacetate 、 copper(II) acetate monohydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(1-phenylvinyl)phenol-d2
  参考文献：
  名称：

  共轭烯烃实现远距离 CH 键的翻转环金属化：邻烯基苯酚与炔烃的区域选择性成环

  摘要：

  在共轭烯烃的辅助下，揭示了一种区域选择性翻转环金属化，用于在邻烯基酚的两个遥远的 C−H 键上实现炔烃的成环。环化伴随着环化，奖励罕见的三重 C−H 官能化。利用扩展共轭或叔羟基配位的杠杆作用，该反应对于一系列不对称炔烃也是完全区域选择性的。

  DOI：

  10.1002/chem.202303245

文献信息

• Rhodium(<scp>iii</scp>)-catalyzed [5+1] annulation of 2-alkenylphenols with maleimides: access to highly functionalized spirocyclic skeletons
  作者：Anil Kumar、Kandikere Ramaiah Prabhu

  DOI：10.1039/d1cc01758f

  日期：——

  A new edition of [5+1] annulation reaction of maleimides with 2-alkenylphenols has been discovered under a Rh(III)-catalytic system. The process leads to an efficient synthesis of valued spirocyclic scaffolds bearing an oxygen-containing spiro carbon in a single step and shows a broad substrate scope with good functional group tolerance. The synthetic utility has been exemplified by synthesizing highly

  在Rh( III )-催化体系下发现了马来酰亚胺与2-烯基苯酚的[5+1]环化反应的新版本。该过程导致在单个步骤中有效合成带有含氧螺碳的有价值的螺环支架，并显示出具有良好官能团耐受性的广泛底物范围。合成效用已通过合成高度官能化的 2,2-二取代-2 H-色烯骨架和低催化剂负载的克级合成来举例说明。
• Rhodium-Catalyzed Coordination-Assisted Regioselective and Migratory Three-Point Double Annulation of <i>o</i>-Alkenyl Phenols with Tertiary Propargyl Alcohols
  作者：Attunuri Nagireddy、Ramesh Kotipalli、Jagadeesh Babu Nanubolu、Maddi Sridhar Reddy

  DOI：10.1021/acs.orglett.2c01819

  日期：2022.7.22

  disclose herein a Rh(III)-catalyzed migratory three-point double annulation of o-alkenyl phenols with propargyl alcohols for de novo construction of naphtho furan derivatives in a regio- and chemoselective manner. The protocol orchestrates two new rings with four new bonds in one operation without the need for any additive. Necessary labeled and control experiments are conducted to elucidate the reaction

  我们在此公开了 Rh(III) 催化的邻烯基酚与炔丙醇的迁移三点双环化，用于以区域选择性和化学选择性的方式从头构建萘并呋喃衍生物。该协议在一次操作中编排了两个新环和四个新键，而无需任何添加剂。进行必要的标记和对照实验以阐明反应机理。除了形成额外的（呋喃）环外，叔羟基被发现对于通过与铑螯合以形成关键的螺环中间体来控制炔烃的区域选择性插入以及通过不寻常和选择性的烯烃重排来强制扩环都是至关重要的。该协议具有可扩展性，并显示出对天然产物后期功能化的耐受性。
• 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.