(-)-2,2-Dimethyl-6-(3-benzyloxy-2-hydroxypropyl)-1,3-dioxin-4-one | 139210-88-1

• 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: (-)-2,2-Dimethyl-6-(3-benzyloxy-2-hydroxypropyl)-1,3-dioxin-4-one
• 英文别名: 6-(2-hydroxy-3-phenylmethoxypropyl)-2,2-dimethyl-1,3-dioxin-4-one
• CAS: 139210-88-1
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: HGWXIOIQMSBZOU-UHFFFAOYSA-N

物化性质

• 沸点：
  470.1±45.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-2,2-Dimethyl-6-(3-benzyloxy-2-hydroxypropyl)-1,3-dioxin-4-one 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以84%的产率得到6-((benzyloxy)methyl)-dihydro-3H-pyran-2,4-dione
  参考文献：
  名称：

  Two lactone formation reactions from 1,3-dioxin-4-ones having hydroxyalkyl group at the 6-position: Difference in ring opening and closure

  摘要：

  Two methods (A: ring opening to acylketenes followed by intramolecular ketene trapping and B: methoxide-mediated ring opening followed by cyclization of the hydroxy esters thus formed) have become available for the synthesis of lactones and/or cyclic ethers from 1,3-dioxin-4-ones having 1-approximately 4-hydroxyalkyl group at the 6-position. Mechanism and scope of both methods have been clarified.

  DOI：

  10.1016/s0040-4020(01)86522-4
• 作为产物：
  描述：

  2,2,6-三甲基-4H-1,3-二英-4-酮 在 六甲基磷酰三胺 、 sodium tetrahydroborate 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (-)-2,2-Dimethyl-6-(3-benzyloxy-2-hydroxypropyl)-1,3-dioxin-4-one
  参考文献：
  名称：

  Two lactone formation reactions from 1,3-dioxin-4-ones having hydroxyalkyl group at the 6-position: Difference in ring opening and closure

  摘要：

  Two methods (A: ring opening to acylketenes followed by intramolecular ketene trapping and B: methoxide-mediated ring opening followed by cyclization of the hydroxy esters thus formed) have become available for the synthesis of lactones and/or cyclic ethers from 1,3-dioxin-4-ones having 1-approximately 4-hydroxyalkyl group at the 6-position. Mechanism and scope of both methods have been clarified.

  DOI：

  10.1016/s0040-4020(01)86522-4

文献信息

• Assembly of Four Diverse Heterocyclic Libraries Enabled by Prins Cyclization, Au-Catalyzed Enyne Cycloisomerization, and Automated Amide Synthesis
  作者：Jiayue Cui、David I. Chai、Christopher Miller、Jason Hao、Christopher Thomas、JingQi Wang、Karl A. Scheidt、Sergey A. Kozmin

  DOI：10.1021/jo301061r

  日期：2012.9.7

  simple one-flask operation starting with readily available amines, ketoesters, and unsaturated anhydrides. The use of tetrahydropyran-containing ketoesters, which were rapidly assembled by our Prins cyclization protocol, enabled efficient fusion of pyran and piperidinone cores. A newly developed Au(I)-catalyzed cycloisomerization of alkyne-containing enamides further expanded heterocyclic diversity by

  我们描述了有效组装四个新杂环库的统一合成策略。合成开始于创建一系列结构不同的吡咯烷酮或哌啶酮。此类化合物是从容易获得的胺、酮酯和不饱和酸酐开始的简单单瓶操作中获得的。使用由我们的 Prins 环化方案快速组装的含四氢吡喃的酮酯，能够有效地融合吡喃和哌啶酮核心。新开发的 Au(I) 催化的含炔烯酰胺的环异构化通过提供快速进入广泛的双环和三环二酰胺进一步扩展了杂环的多样性。
• Optically active 2,2-dimethyl-1,3-dioxin-4-ones and method for preparing
  申请人：Chisso Corporation

  公开号：US05256800A1

  公开（公告）日：1993-10-26

  There are provided novel and optically active 2,2-dimethyl-1,3-dioxin-4-ones which are useful as starting materials for physiologically active compounds, functional materials or the like. Furthermore, a method for preparing an optically active compound comprises reacting a racemic 1,3-dioxin-4-one with vinylacetate in the presence of lipase to resolve the racemic compound into optically active compound represented by the formula (3) ##STR1## and an optically active compound represented by the formula (4) ##STR2## which is an antipode of the compound represented by the formula (3).

  提供了一种新型的光学活性2,2-二甲基-1,3-二氧杂环丁酮，可用作生理活性化合物、功能材料等的起始材料。此外，一种制备光学活性化合物的方法包括在脂肪酶存在下，将外消旋1,3-二氧杂环丁酮与醋酸乙烯基反应，将外消旋化合物分解成代表公式（3）的光学活性化合物和代表公式（4）的光学活性化合物，后者是代表公式（3）化合物的对映异构体。
• Optically active 1,3-dioxin-4-ones
  申请人：CHISSO CORPORATION

  公开号：EP0500364A1

  公开（公告）日：1992-08-26

  Optically active 1,3-dioxin-4-ones have the formula : wherein n is a value of 1 to 3 ; X is a hydrogen atom, a benzyloxy group, a chlorine atom or N3 ; Y is a hydrogen atom or an acetyl group ; the symbol * represents an asymmetric carbon atom ; and the substituent chain is present at the 5- or 6-position ; provided that when n is 1 and X is a benzyloxy group, a chlorine atom or N3, the substituent is present at the 6-position ; when n is 2 and X is a hydrogen atom the substituent is present at the 5-position ; and when n is 3 and X is a hydrogen atom, the substituent is present at the 6-position. Various methods for the preparation are disclosed.

  具有光学活性的 1,3-二恶英-4-酮的化学式为 ： 其中 n 的值为 1 至 3；X 为氢原子、苄氧基、氯原子或 N3；Y 为氢原子或乙酰基；符号 * 代表不对称碳原子；取代基链存在于 5 位或 6 位；当 n 为 1 时，X 为苄氧基、氯原子或 N3，取代基存在于 6 位；当 n 为 2 时，X 为氢原子，取代基存在于 5 位；当 n 为 3 时，X 为氢原子，取代基存在于 6 位。 已公开的制备方法有多种。
• US5256800A
  申请人：——

  公开号：US5256800A

  公开（公告）日：1993-10-26
• US5292891A
  申请人：——

  公开号：US5292891A

  公开（公告）日：1994-03-08