(2,2-dimethyl-1,3-dioxolane-4-yl)methyl n-pentanoate | 20620-18-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2,2-dimethyl-1,3-dioxolane-4-yl)methyl n-pentanoate
• 英文别名: (RS)-1,2-O-isopropylidene glycerol valerate；(2,2-dimethyl-1,3-dioxolan-4-yl)methyl pentanoate；(RS)-1,2-O-isopropylidene glycerol pentanoate；(+/-)-2,2-dimethyl-4-valeryloximethyl-[1,3]dioxolane；(+/-)-2,2-Dimethyl-4-valeryloxymethyl-[1,3]dioxolan
• CAS: 20620-18-2
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: ISFHESIXABVYJU-UHFFFAOYSA-N

物化性质

• 沸点：
  266.2±20.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二十二酸 、 (2,2-dimethyl-1,3-dioxolane-4-yl)methyl n-pentanoate 在 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以60%的产率得到1-Valeroyl-2,3-dibenenoyl-rac-glycerol
  参考文献：
  名称：

  New Synthetic Strategies Toward Pure Two-Component Triglycerides

  摘要：

  纯双组分甘油三酯是通过新的合成策略制备的，这些策略涉及甘油醛酸酯的酰基水解裂解。

  DOI：

  10.1055/s-1999-2936
• 作为产物：
  描述：

  丙酮缩甘油 生成 (2,2-dimethyl-1,3-dioxolane-4-yl)methyl n-pentanoate
  参考文献：
  名称：

  Martin; Santos, Anales de la Real Sociedad Espanola de Fisica y Quimica, 1953, vol. 49, p. 723,726

  摘要：

  DOI：

文献信息

• Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group**
  作者：Guillaume Force、Anna Perfetto、Robert J. Mayer、Ilaria Ciofini、David Lebœuf

  DOI：10.1002/anie.202105882

  日期：2021.9

  towards their synthesis, notably from seco-acids, a macrolactonization promoter system that is effective, selective, flexible, readily available, and, insofar as possible, compatible with manifold functional groups is still lacking. Herein, we describe a strategy that relies on the formation of a mixed anhydride incorporating a pentafluorophenyl group which, due to its high electronic activation enables

  大环内酯是一类特殊的天然和合成产品，在精细化学品和制药行业有着广泛的应用。尽管在合成方面取得了所有进展，特别是从seco-酸，一种有效的、选择性的、灵活的、容易获得的并且尽可能与多种官能团相容的大环内酯化促进剂系统仍然缺乏。在这里，我们描述了一种策略，该策略依赖于形成包含五氟苯基的混合酸酐，由于其高电子活化，可以方便地获得具有广泛多功能性的大环内酯、大二内酯和酯。进行动力学研究和 DFT 计算以合理化五氟苯基在大环内酯化反应中的反应性。
• Direct Macrolactonization of Seco Acids via Hafnium(IV) Catalysis
  作者：Mylène de Léséleuc、Shawn K. Collins

  DOI：10.1021/acscatal.5b00082

  日期：2015.3.6

  Efficient direct macrolactonization of seco acids can be catalyzed by Hf(OTf)4 in high yields, forming water as the sole byproduct. The Hf(OTf)4 catalyst possesses unique reactivity characteristics relative to other Lewis acids, as it promotes macrolactonization over hydrolysis even in the presence of excess water. In addition to forming a variety of macrolactones and benzolactones (55–90%), intermolecular

  Hf（OTf）4可以高产率催化山梨酸的高效直接大环内酯化，形成水作为唯一的副产物。Hf（OTf）4相对于其他路易斯酸，该催化剂具有独特的反应特性，因为即使在存在过量水的情况下，它也比水解作用促进大内酯化。除了形成各种大分子内酯和苯并内酯（55-90％）外，羧酸和醇的分子间直接酯化也是可能的，并证明了与常见的氨基甲酸酯，甲硅烷基醚，烷氧基甲基醚和乙缩醛保护基的相容性。开发的所有大环内酯化和酯化方法都是操作简单的“一锅法”反应，可利用市售催化剂，而无需缓慢添加或共沸技术。
• Solvent system and compositions therewith
  申请人：RHODIA POLIAMIDA E ESPECIALIDADES LTDA

  公开号：US10239116B2

  公开（公告）日：2019-03-26

  The present invention relates to a solvent system characterized by the fact that is comprises one or more dioxolane-derived esters of formula I where R1, R2 and R3 are the same or different, selected from hydrogen, alkyl, alkenyl and phenyl, and n is an integer between 1 and 5.

  本发明涉及一种溶剂体系，其特征在于该体系包含一种或多种式 I 的二氧戊环衍生酯 其中 R1、R2 和 R3 相同或不同，选自氢、烷基、烯基和苯基，n 为 1 至 5 之间的整数。
• Lipase-mediated desymmetrization of glycerol with aromatic and aliphatic anhydrides
  作者：Daniela I. Batovska、Shuichirou Tsubota、Yasuo Kato、Yasuhisa Asano、Makoto Ubukata

  DOI：10.1016/j.tetasy.2004.09.033

  日期：2004.11

  Chirazyme L-2 (Candida antarctica) catalyzed esterification of glycerol with aromatic and aliphatic anhydrides in 1,4-dioxane is described. All the aromatic monoacylglycerols (MAGs) were produced as (R)-enantiomers, while aliphatic MAGs were obtained either as racemic mixtures or the (S)-enantiomers. The influence of substituted aromatic rings, chain length, and presence of a conjugated double bond in the acyl donor moiety on the enantiotopic selectivity as well as the efficiency of the enzyme was studied. (C) 2004 Elsevier Ltd. All rights reserved.
• Enhanced enantioselectivity of Bacillus coagulans in the hydrolysis of 1,2-O-isopropylidene glycerol esters by thermal knock-out of undesired enzymes
  作者：Diego Romano、Francesco Falcioni、Diego Mora、Francesco Molinari、Andreas Buthe、Marion Ansorge-Schumacher

  DOI：10.1016/j.tetasy.2004.12.021

  日期：2005.2

  The enantioselective hydrolysis of different (RS)-1,2-O-isopropylidene glycerol esters has been achieved with whole cells of Bacillus coagulans NCIMB 9365 furnishing the (S)-alcohol as the major enantiomer. The reaction is catalysed by a thermostable cell-bound carboxylesterase and improvement of the enantioselectivity has been achieved by heat treatment of the whole cells, which causes the knock-outs a non-enantioselective competing enzyme. Thermally-treated cells hydrolysed (RS)-1,2-O-isopropylidene glycerol esters with high enantioselectivity, the highest enantiomeric ratio (80-100) being observed for the benzoate. The biocatalyst displayed good stability and could be re-used after filtration for 12 cycles before showing significant loss of activity; repeated biotransformation batches allowed the recovery of 9.55 g/L of enantiomerically pure (S)-isopropylideneglycerol benzoate starting from 24.0 g/L of the racemic mixture. (C) 2005 Elsevier Ltd. All rights reserved.