4-phenyltetrahydropyran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-phenyltetrahydropyran-2-one
• 英文别名: 4-phenyltetrahydro-2H-pyran-2-one；4-phenyltetrahydro-2-pyranone；4-Phenyl-tetrahydropyran-2-one；4-phenyloxan-2-one
• 化学式: C₁₁H₁₂O₂
• mdl: MFCD11036263
• 分子量: 176.215
• InChiKey: ONMHULVUDDUGQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenyltetrahydropyran-2-one 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 2.0h， 以75%的产率得到2-hydroxy-4-phenyltetrahydropyran
  参考文献：
  名称：

  The effect of pre-existing stereocenters in the intramolecular asymmetric Stetter reaction

  摘要：

  A series of disubstituted cyclopentanones have been synthesized by the intramolecular Stetter reaction. Racemic substrates containing one chiral center were used, allowing us the opportunity to observe a parallel kinetic resolution in the synthesis of 2,3- and 2,4disubstituted cyclopentanones. The Stetter reaction of 2,5-disubstituted cyclopentanones proved to be substrate controlled, resulting in the selective formation of the cis-diasteroiners with low ee. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.121
• 作为产物：
  描述：

  3-苯基戊二酸单乙酯 在 锂硼氢 、 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 4-phenyltetrahydropyran-2-one
  参考文献：
  名称：

  Enzymatic desymmetrization of 3-arylglutaric acid anhydrides

  摘要：

  Optically active (R)- and (S)-3-arylglutaric acid monoesters 3 were synthesized in quantitative yields and good stereoselectivities by lipase-catalyzed desymmetrization of the corresponding 3-arylglutaric anhydrides 2 with alcohols. It was observed that the stereochemical outcome of the reaction was influenced by the substituents present on the aromatic ring. The influence of the enzyme, alcohol, and solvent was systematically examined. Absolute configurations of the monoesters 3 were assigned by chemical correlation to corresponding lactones 4. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.025

文献信息

• Rhodium-catalysed enantioselective synthesis of 4-arylchroman-2-ones
  作者：Joseph C. Allen、Gabriele Kociok-Köhn、Christopher G. Frost

  DOI：10.1039/c1ob06586f

  日期：——

  The rhodium-catalysed enantioselective 1,4-addition of organoboron reagents to arylidene Meldrum's acids as acceptors, allows convenient access to 4-arylchroman-2-ones with good to excellent levels of enantioselectivity. The use of silyl-protected dioxaborinanes as donors was found to be advantageous to achieving good yields of product under anhydrous conditions.

  铑催化的手性选择性1,4-加成反应：以芳叉型梅尔魏因酸作为受体，有机硼试剂作为供体，方便地合成具有良好至优异手性选择性的4-芳基色满-2-酮。使用硅基保护的二氧硼烷作为供体，在无水条件下有利于实现高产率的产品合成。
• Ti/Ni-Mediated Inter- and Intramolecular Conjugate Addition of Aryl and Alkenyl Halides and Triflates
  作者：Irene R. Márquez、Delia Miguel、Alba Millán、M. Luisa Marcos、Luis Álvarez de Cienfuegos、Araceli G. Campaña、Juan M. Cuerva

  DOI：10.1021/jo402626u

  日期：2014.2.21

  extent, chlorides and triflates to α,β-unsaturated carbonyls at room temperature, without requiring the previous formation of an organometallic nucleophile. The reaction proceeds inter- and intramolecularly with good functional group compatibility, which is key for the development of free protecting group methodologies. Carbo- and heterocycles of five- and six-membered rings are obtained in good yields.

  在这项工作中，我们表明，镍催化剂和Cp 2 TiCl的独特组合可以在室温下直接共轭添加芳基和链烯基碘化物，溴化物，并在较小程度上将氯化物和三氟甲磺酸盐生成α，β-不饱和羰基。 ，而无需事先形成有机金属亲核试剂。该反应在分子间和分子内以良好的官能团相容性进行，这是开发自由保护基方法的关键。五元环和六元环的碳环和杂环以高收率获得。此外，从循环伏安法，UV-vis和HRTEM测量中获得了有关机理的一些见解。
• Aerobic Lactonization of Diols by Biomimetic Oxidation
  作者：Yoshinori Endo、Jan-E. Bäckvall

  DOI：10.1002/chem.201102168

  日期：2011.11.4

  Coming up for air: Highly efficient aerobic lactonization can be carried out by a biomimetic oxidation system based on coupled redox catalysts (ruthenium catalyst and electron transfer mediators). This system leads to a low‐energy electron transfer from diol to molecular oxygen. Various diols were aerobically oxidized to the corresponding five‐ to nine‐membered lactones in good to high yields under

  空气进入：高效的好氧内酯化反应可以通过基于偶合氧化还原催化剂（钌催化剂和电子传递介体）的仿生氧化系统进行。该系统导致低能电子从二醇转移到分子氧。在温和的反应条件下，各种二醇被好氧氧化成相应的五元至九元内酯（见方案）。
• [EN] PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS<br/>[FR] PROCEDE DE PREPARATION DE COMPOSES ENRICHIS EN ENANTIOMERES
  申请人：DSM IP ASSETS BV

  公开号：WO2003099745A1

  公开（公告）日：2003-12-04

  Process for the preparation of enantiomerically enriched compounds with Formula Ar-C(R1)-C(R2)-Z wherein Ar represents an optionally substituted (hetero)aryl group, R1 and R2, each independently, represent H, an alkyl, (hetero)aryl, dialkylamino, amido, thioether, alkoxy or aryloxy group with the proviso that not both R1 and R2 represent H, or R1 and R2 form together with the C-atoms to which they are bound a (hetero)alkyl or (hetero) alkenyl ring and Z represents an electron withdrawing group, in which process a boronic acid derivate of Formula Ar-B(OR3)OR4 or its anhydride, wherein Ar is as described above and R3 and R4, each independently, represent H or an alkyl group, is reacted with an olefinic unsaturated compound with Formula R2 - C = C - (R1)Z, wherein R1, R2 and Z are as described above, in the presence of a transition metal catalyst comprising a transition metal chosen from Cu and group VIII of the Periodic Table and an enantiomerically enriched ligand L, having the Formula (I) where Cn together with the two O-atoms and the P-atom forms a substituted or non-substituted ring with 2-6 C-atoms, R5 and R6 each independently stand for H, an optionally substituted alkyl, aryl, alkaryl, or aralkyl group, or represent the group with Formula (II) wherein Cn1 may have the same meanings as given for Cn and B represents a bridging group, or R5 and R6 may form a heterocyclic ring together with the N-atom to which they are bound.

  制备具有Ar-C(R1)-C(R2)-Z式的对映富集化合物的过程，其中Ar代表可选择取代的(杂)芳基团，R1和R2分别独立地代表H、烷基、(杂)芳基、二烷基氨基、酰胺、硫醚、烷氧基或芳氧基团，但R1和R2不同时代表H，或者R1和R2与它们结合的C原子一起形成(杂)烷基或(杂)烯基环，Z代表一个电子吸引基团，在该过程中，以Formula Ar-B(OR3)OR4或其酐的硼酸衍生物为反应物，其中Ar如上所述，R3和R4分别独立地代表H或烷基团，与Formula R2 - C = C - (R1)Z的烯烃不饱和化合物反应，其中R1、R2和Z如上所述，在Cu和周期表第VIII族的过渡金属选择的过渡金属催化剂存在下，以对映富集的配体L为特征，其具有Formula (I)，其中Cn与两个氧原子和磷原子一起形成具有2-6个C原子的取代或非取代环，R5和R6分别独立地代表H、可选择取代的烷基、芳基、烷芳基或芳基基团，或代表具有Formula (II)的基团，其中Cn1可能具有与Cn相同的含义，B代表一个桥联基团，或者R5和R6可以与它们结合的N原子一起形成一个杂环。
• Organo[2-(hydroxymethyl)phenyl]dimethylsilanes as Mild and Reproducible Agents for Rhodium-Catalyzed 1,4-Addition Reactions
  作者：Yoshiaki Nakao、Jinshui Chen、Hidekazu Imanaka、Tamejiro Hiyama、Yoshitaka Ichikawa、Wei-Liang Duan、Ryo Shintani、Tamio Hayashi

  DOI：10.1021/ja071969r

  日期：2007.7.1

  achievement of the corresponding enantioselective transformations using the tetraorganosilicon reagents, providing the silicon-based approach to optically active ketones and substituted piperidones that serve as synthetic intermediates of pharmaceuticals. A rhodium alkoxide species is suggested to be responsible for a transmetalation step on the basis of the observed kinetic resolution of a racemic chiral phenylsilane

  稳定且可重复使用的四有机硅试剂、烯基-、芳基-和甲硅烷基[2-(羟甲基)苯基]二甲基硅烷，在温和的铑催化下与 α,β-不饱和羰基受体发生 1,4-加成反应。该反应耐受多种官能团，适用于克级合成。手性二烯配体的使用允许使用四有机硅试剂实现相应的对映选择性转化，为用作药物合成中间体的光学活性酮和取代哌啶酮提供基于硅的方法。根据观察到的对映选择性 1 中的外消旋手性苯基硅烷的动力学分辨率，建议铑醇盐物种负责金属转移步骤，