5-benzyl-2,2,5-trimethyl-1,3-dioxane-4,6-dione | 83540-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-benzyl-2,2,5-trimethyl-1,3-dioxane-4,6-dione
• 英文别名: 5-Methyl-5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxane
• CAS: 83540-59-4
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: YDBUGCWLOOQMEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-benzyl-2,2,5-trimethyl-1,3-dioxane-4,6-dione 在 (+)-(2S,8aS)-(camphorylsulfonyl)oxaziridine 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.67h， 生成 (R)-Menthyl (2R)-2-hydroxy-2-methyl-3-phenylpropionate
  参考文献：
  名称：

  Enantioselective Synthesis of 2-Methyl-2-hydroxy-.gamma.-butyrolactone and Its Application in the Asymmetric Synthesis of Frontalin and Mevalonolactone

  摘要：

  The asymmetric hydroxylation of the enolates of fully substituted acyclic ester 8 and lactone 10 with (camphorylsulfonyl)oxaziridines 1a-c was studied. The stereoselectivities of the tertiary alpha-hydroxy carbonyl products were highly dependent on the enolate structure, the oxidizing reagents, and the reaction conditions. While high diastereoselectivity (up to 94%) was obtained for enolates of fully substituted menthol ester 8 with substoichiometric amounts of oxaziridine 1a, the yields were unsatisfactory. On the other hand, the enantioselective alpha-hydroxylation of the sodium enolate of 2-methyl-gamma-butyrolactone (10) with [(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine (1c) afforded alpha-hydroxy lactone 11a in 70% yield and 84% ee. The enantiomeric excess was improved to > 93% ee by crystallization of the corresponding benzoyl ester 11c. The utility of both enantiomers of 11c were demonstrated in the formal asymmetric syntheses of the pheromone, (1S,5R)-(-)-frontalin (13) and in the asymmetric synthesis of (R)-(-)-mevalonolactone (20).

  DOI：

  10.1021/jo00124a030
• 作为产物：
  描述：

  5-亚苄基-2,2-二甲基-1,3-二恶烷-4,6-二酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 5-benzyl-2,2,5-trimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  One Pot Synthesis of Monoalkylated and Mixed, Dialkylated Meldrum's Acid Derivatives

  摘要：

  A simple one pot method, involving sequential Knoevenagel condensation of Meldrum's acid with aromatic aldehydes, conjugate reduction of ylidene Meldrum's acid using sodium borohydride followed by alkylation, to prepare mixed dialkylated derivatives of Meldrum's acid is described.

  DOI：

  10.1081/scc-120027234

文献信息

• Multicomponent decarboxylative allylations
  作者：Yamuna Ariyarathna、Jon A. Tunge

  DOI：10.1039/c4cc07253g

  日期：——

  The reaction of Meldrum's acid, pyrrolide, and allyl carbonates allows a multicomponent decarboxylative coupling to form allylated acyl pyrroles. This strategy is made possible by the in situ formation of β-oxo carboxylates from Meldrum's acid. Subsequent decarboxylative enolate formation and electrophilic allylation complete the reaction. Addition of benzylidene malononitriles as good Michael acceptors allow a 4-component interceptive decarboxylative allylation.

  梅氏酸、吡咯烷和烯丙基碳酸酯的反应可以通过多组分脱羧偶联生成烯丙基酰基吡咯。这种策略是通过原位形成梅氏酸的β-氧代羧酸盐而实现的。随后形成的脱羧烯醇和亲电烯丙基化完成了反应。加入亚苄基丙二腈作为良好的迈克尔受体，可以进行 4 组分互作脱羧烯丙基化反应。
• Selective Reductions of Cyclic 1,3-Diesters by Using SmI₂and H₂O
  作者：Karl D. Collins、Juliana M. Oliveira、Giuditta Guazzelli、Brice Sautier、Sara De Grazia、Hiroshi Matsubara、Madeleine Helliwell、David J. Procter

  DOI：10.1002/chem.201000632

  日期：2010.9.3

  SmI2/H2O reduces cyclic 1,3‐diesters to 3‐hydroxyacids with no over reduction. Furthermore, the reagent system is selective for cyclic 1,3‐diesters over acyclic 1,3‐diesters, and esters. Radicals formed by one‐electron reduction of the ester carbonyl group have been exploited in intramolecular additions to alkenes. The ketal unit and the reaction temperature have a marked impact on the diastereoselectivity

  SmI 2 / H 2 O可以将环状1,3-二酯还原为3-羟基酸，且不会过度还原。此外，该试剂系统对环状1,3-二酯的选择要高于非环状1,3-二酯和酯的选择。通过单电子还原酯羰基形成的自由基已在分子内加成烯烃中得到利用。缩酮单元和反应温度对环化的非对映选择性具有显着影响。当起始环二酯中存在两个烯烃并导致形成两个具有良好立体控制性的环和四个立体中心时，可能会发生级联级联反应。
• ADHESIVE RESIN COMPOSITION, LAMINATE, AND SELF-STRIPPING METHOD
  申请人：MITSUI CHEMICALS TOHCELLO, INC.,

  公开号：US20140322474A1

  公开（公告）日：2014-10-30

  An adhesive resin composition of the present invention includes an expandable sticky polymer having a structure derived from a Meldrum's acid derivative, or a Meldrum's acid derivative represented by the following general formula (1) and an adhesive resin.

  本发明的粘合树脂组合物包括一种可膨胀的黏性聚合物，其结构源自Meldrum酸衍生物，或由以下通式（1）表示的Meldrum酸衍生物和粘合树脂组成。
• ADHESIVE RESIN COMPOSITION, LAMINATE BODY, AND SELF-PEELING METHOD
  申请人：Mitsui Chemicals Tohcello Co., Ltd.

  公开号：EP2792725A1

  公开（公告）日：2014-10-22

  An adhesive resin composition of the present invention includes an expandable sticky polymer having a structure derived from a Meldrum's acid derivative, or a Meldrum's acid derivative represented by the following general formula (1) and an adhesive resin.

  本发明的粘合剂树脂组合物包括一种可膨胀的粘性聚合物，其结构来源于梅尔德伦酸衍生物，或由以下通式（1）表示的梅尔德伦酸衍生物和一种粘合剂树脂。
• Synthesis of Isopropylidene Dialkylmalonates under Phase-Transfer Catalyzed Conditions
  作者：CHENG-CHU Chan、XIAN Huang

  DOI：10.1055/s-1982-29829

  日期：——