(2R)-2,3-dihydro-2-n-propyl-4H-pyran-4-one | 941314-01-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R)-2,3-dihydro-2-n-propyl-4H-pyran-4-one
• 英文别名: (R)-2,3-dihydro-2-propyl-4H-pyran-4-one；(S)-2,3-dihydro-2-n-propyl-4H-pyran-4-one；(2R)-2-propyl-2,3-dihydropyran-4-one
• CAS: 941314-01-8
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: INSHCENXEBIIHU-MRVPVSSYSA-N

物化性质

• 沸点：
  198.0±15.0 °C(predicted)
• 密度：
  0.991±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-甲氧基-3-三甲基硅氧基-1,3-丁二烯 在 chiral oxazaborolidine 1 三氟乙酸 作用下， 以 乙醚 为溶剂， 反应 15.0h， 生成 (2R)-2,3-dihydro-2-n-propyl-4H-pyran-4-one
  参考文献：
  名称：

  Enantioselective Mukaiyama-aldol and aldol-dihydropyrone annulation reactions catalyzed by a tryptophan-derived oxazaborolidine

  摘要：

  The (S)-tryptophan derived catalyst 1, has been used to effect enantioselective Mukaiyama-aldol and aldol-dihydropyrone annulation reactions of trimethylsilyloxy olefins and, dienes.

  DOI：

  10.1016/s0040-4039(00)60892-4

文献信息

• Methods of performing cycloadditions, reaction mixtures, and methods of performing asymmetric catalytic reactions
  申请人：The University of Chicago

  公开号：US07230125B1

  公开（公告）日：2007-06-12

  Methods of performing cycloadditions are described that include (a) combining a first reactant and a second reactant in a hydrogen bonding solvent to form a reaction mixture; and (b) reacting the first reactant and the second reactant to form a cycloadduct. Methods of performing asymmetric catalytic reactions are also described that include (a) combining a first reactant, a second reactant, and a catalytic amount of a chiral hydrogen-bond donor in a solvent to form a reaction mixture; and (b) reacting the first reactant and the second reactant to form an enantiomeric excess of a reaction product. Reaction mixtures corresponding to these methods are also described.

  描述了进行环加成的方法，包括(a)在氢键合剂溶剂中将第一反应物和第二反应物组合以形成反应混合物；以及(b)使第一反应物和第二反应物发生反应以形成环加成物。还描述了进行不对称催化反应的方法，包括(a)在溶剂中将第一反应物、第二反应物和手性氢键供体的催化剂量组合以形成反应混合物；以及(b)使第一反应物和第二反应物发生反应以形成反应产物的对映体过量。还描述了与这些方法相对应的反应混合物。
• Axially Chiral Biaryl Diols Catalyze Highly Enantioselective Hetero-Diels−Alder Reactions through Hydrogen Bonding
  作者：Aditya K. Unni、Norito Takenaka、Hisashi Yamamoto、Viresh H. Rawal

  DOI：10.1021/ja044076x

  日期：2005.2.1

  Axially chiral 1,1'-biaryl-2,2'-dimethanol (3, BAMOL) family of diols are highly effective catalysts for enantioselective hetero-Diels-Alder reactions between aminosiloxydiene 1 and a wide variety of unactivated aldehydes. The reactions proceed in useful yields and excellent enantioselectivities. The diols function in the same capacity as Lewis acids, by activating the aldehyde carbonyl group through

  轴向手性 1,1'-联芳基-2,2'-二甲醇 (3, BAMOL) 二醇家族是氨基甲硅烷氧基二烯 1 和多种未活化醛之间的对映选择性杂 Diels-Alder 反应的高效催化剂。反应以有用的产率和优异的对映选择性进行。二醇的功能与路易斯酸相同，通过氢键活化醛羰基。
• Planar-Chiral Bis-silanols and Diols as H-Bonding Asymmetric Organocatalysts
  作者：Christine Beemelmanns、Ralph Husmann、Daniel K. Whelligan、Salih Özçubukçu、Carsten Bolm

  DOI：10.1002/ejoc.201200548

  日期：2012.6

  enantiopure planar-chiral bis-silanols and bis-carbinols were obtained in good yields. The catalytic activities of the bis-silanols were analyzed by monitoring HDA reactions between Rawal's diene and aldehydes by in situ IR spectroscopy and comparing the resulting data with those obtained in catalyses with the corresponding bis-carbinol derivatives. The results show for the first time that planar-chiral bis-silanols

  描述了平面手性双硅烷醇 3a-d 的成功开发及其在异狄尔斯-阿尔德 (HDA) 反应中作为不对称有机催化剂的应用。通过将市售的甲硅烷基亲电试剂添加到二锂化的 [2.2] 对环芳烷衍生物中，然后进行硅烷氧化，可以轻松制备所有前体。通过向双甲氧基羰基衍生物 6 添加合适的格氏试剂制备了类似的双甲醇 7a-c。外消旋和对映纯平面手性双硅烷醇和双甲醇均以良好的收率获得。双硅烷醇的催化活性是通过原位红外光谱监测拉瓦尔二烯和醛之间的 HDA 反应并将所得数据与相应双甲醇衍生物在催化中获得的数据进行比较来分析的。
• Chiral rare earth organophosphates as homogeneous Lewis acid catalysts for the highly enantioselective hetero-Diels–Alder reactions
  作者：Hiroshi Furuno、Tetsuji Hayano、Takeshi Kambara、Yuichi Sugimoto、Takeshi Hanamoto、Yumiko Tanaka、Yong Zhi Jin、Takumi Kagawa、Junji Inanaga

  DOI：10.1016/j.tet.2003.06.011

  日期：2003.12

  Various trivalent rare earth-chiral phosphate complexes [(R)-l-RE, (R)-3-RE, and (R)-4-Ce] were prepared and evaluated as a Lewis acid catalyst for the asymmetric hetero-Diels-Alder reaction of aldehydes with the Danishefsky's diene. Some of them effectively promoted the reaction at room temperature in the presence or absence of achiral additives under homogeneous conditions to afford the corresponding cycloadducts with high ee's (up to 99% ee). During these reactions, remarkably high asymmetric amplifications (positive nonlinear effects) were observed as the first example in the metal ion-chiral ligand 1:3 catalytic system. A scandium catalyst bearing the H-8-BNP ligand, (R)-3-Sc, could be recovered after the reaction and successfully reused for the next round of reactions. In addition, the hetero-Diels-Alder reaction of alpha-keto esters was effectively catalyzed by the ytterbium complex, (R)-l-Yb, without any additives thus producing the asymmetric quaternary carbon in excellent enantioselectivities (up to > 99% ee). (C) 2003 Elsevier Ltd. All rights reserved.
• PATERSON, IAN;OSBORNE, SIMON, TETRAHEDRON LETT., 31,(1990) N5, C. 2213-2216
  作者：PATERSON, IAN、OSBORNE, SIMON

  DOI：——

  日期：——