(R)-2-<(Phenylmethoxy)methyl>-2,3-dihydro-4H-pyran-4-one

• 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: (R)-2-<(Phenylmethoxy)methyl>-2,3-dihydro-4H-pyran-4-one
• 英文别名: (R)-2-benzyloxymethyl-2,3-dihydro-4H-pyran-4-one；(R)-2-(benzyloxymethyl)-2,3-dihydropyran-4-one；2-benzyloxymethyl-2,3-dihydro-4H-pyran-4-one；(2R)-2-(phenylmethoxymethyl)-2,3-dihydropyran-4-one
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: IRQQAWBBQRVPSH-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苄氧基乙醛 在 titanium(IV) isopropylate 、 S-1,1'-联-2-萘酚 4 A molecular sieve 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 81.17h， 生成 (R)-2-<(Phenylmethoxy)methyl>-2,3-dihydro-4H-pyran-4-one
  参考文献：
  名称：

  Catalytic Enantioselective Synthesis of Dihydropyrones via Formal Hetero Diels-Alder Reactions of "Danishefsky's Diene" with Aldehydes

  摘要：

  DOI：

  10.1021/jo00124a001

文献信息

• A Highly Enantioselective Hetero-Diels−Alder Reaction of Aldehydes with Danishefsky's Diene Catalyzed by Chiral Titanium(IV) 5,5‘,6,6‘,7,7‘,8,8‘-Octahydro-1,1‘-bi-2-naphthol Complexes
  作者：Bin Wang、Xiaoming Feng、Yaozong Huang、Hui Liu、Xin Cui、Yaozhong Jiang

  DOI：10.1021/jo016240u

  日期：2002.4.1

  products with very high enantioselectivity (up to 99% ee) and yield (92%). The hetero-Diels-Alder reaction of other aldehydes with 1 under the catalysis of TiHBOL is a general reaction which proceeds well with very high enantioselectivity and isolated yield for various aldehydes at 0 degrees C to room temperature. Based on the experimental results, the proposed mechanism of the hetero-Diels-Alder reaction

  研究了手性路易斯酸对醛与Danishefsky's diene（1）之间的杂Diels-Alder反应的催化作用。作为苯甲醛和1之间杂Diels-Alder反应的催化剂，已研究了各种不同配体和路易斯酸的组合，并发现容易获得的Ti（IV）-H（8）-BINOL（TiHBOL配合物是反应的非常有效的催化剂，导致产物具有很高的对映选择性（高达99％ee）和产率（92％）。在TiHBOL催化下，其他醛与1的杂Diels-Alder反应是一种常规反应，在0℃至室温下，该反应进行得很好，具有很高的对映选择性并分离出各种醛。根据实验结果，
• SYNTHETIC STUDIES OF ANTITUMOR MACROLIDE LAULIMALIDE: ENANTIOSELECTIVE SYNTHESIS OF THE C3-C14 SEGMENT BY A CATALYTIC HETERO DIELS-ALDER STRATEGY
  作者：Arun K Ghosh、Packiarajan Mathivanan、John Cappiello

  DOI：10.1016/s0040-4039(97)00416-4

  日期：1997.4

  The C3-C14 segment of the novel antitumor agent laulimalide has been constructed enantioselectively by utilizing a catalytic asymmetric hetero Diels-Alder reaction of benzyloxyacetaldehyde and Danishefsky's diene followed by Ferrier rearrangement and asymmetric conjugate reaction as the key steps. © 1997 Elsevier Science Ltd.

  以苄氧基乙醛和Danishefsky二烯的催化不对称杂Diels-Alder反应，然后以Ferrier重排和不对称共轭反应为关键步骤，对映选择性地构建了新型抗肿瘤药物月桂马利特的C 3 -C 14链段。© 1997 爱思唯尔科学有限公司。
• A Diels-Alder Approach to Anthrapyran Antibiotics
  作者：Sylvain Collet、André Guingant、Laura Foulgoc、Drissa Sissouma、Michel Evain

  DOI：10.1055/s-0031-1290529

  日期：2012.3

  A new entry to the synthesis of anthrapyran antibiotics has been accomplished through the synthesis of a 4H-anthra[1,2-b]pyran-4,7,12-trione model. The key step features a Diels-Alder reaction between a substituted 5-vinyl-3,4-dihydro-2H-pyran and naphthoquinone as the dienophile. The resulting tetracyclic adduct is then processed towards the targeted trione in a few steps.

  通过合成 4H-anthra[1,2-b]pyran-4,7,12-trione 模型，已经完成了合成蒽吡喃抗生素的新途径。关键步骤是取代 5-乙烯基-3,4-二氢-2H-吡喃和萘醌作为亲二烯体之间的狄尔斯-阿尔德反应。然后通过几个步骤将所得的四环加合物加工成目标三酮。
• Enantioenriched Dihydropyrones from β-Lactone Templates
  作者：G. Greg Zipp、Mark A. Hilfiker、Scott G. Nelson

  DOI：10.1021/ol025607u

  日期：2002.5.1

  [reaction: see text] Optically active 4-substituted 2-oxetanones provide conduits for preparing 2,3-dihydro-4H-pyrone heterocycles. Enantioenriched beta-lactones are prepared by asymmetric catalytic acyl halide-aldehyde cyclocondensation reactions. Hydrazone anion-mediated beta-lactone ring opening and ensuing cyclization-dehydroamination of the derived beta-ketohydrazone afford the desired dihydropyrones

  [反应：见正文]光学活性的4-取代的2-氧杂环丁酮提供了制备2,3-二氢-4H-吡喃酮杂环的通道。通过不对称催化酰基卤-醛-环缩合反应制备对映体富集的β-内酯。dra阴离子介导的β-内酯开环和随后的β-酮ke的环化-脱氢胺化反应提供了所需的二氢吡喃酮（68-81％）。最佳的内酯开环反应条件使多种旋光的4-取代的-2-氧杂环丁烷成为富对映体的2,3-二氢-4H-吡喃酮的有效前体。
• Preparation and reactions of 2-allyl-5-deoxymannose derivatives
  作者：Twana Saleh、Gérard Rousseau

  DOI：10.1016/s0040-4020(02)00150-3

  日期：2002.4

  Reaction of Danishefsky diene with benzyloxyethanal led to a pyrone which was transformed in 4-6 steps to different 5-deoxymannose derivatives, useful intermediates for the synthesis of natural product such as hemibrevetoxin. (C) 2002 Elsevier Science Ltd. All rights reserved.