(R)-2-methylene-4-phenyl-1,3-dioxolane | 103637-53-2

• 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-methylene-4-phenyl-1,3-dioxolane
• 英文别名: (R)-4-Phenyl-2-methylene-1,3-dioxolane；1,3-Dioxolane, 2-methylene-4-phenyl-, (R)-；(4R)-2-methylidene-4-phenyl-1,3-dioxolane
• CAS: 103637-53-2
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: FHTWQMHOTBIHEP-JTQLQIEISA-N

物化性质

• 沸点：
  276.3±40.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-methylene-4-phenyl-1,3-dioxolane 以 氘代二甲亚砜 为溶剂， 反应 2.05h， 生成
  参考文献：
  名称：

  Facial Selectivity in Cycloadditions of a Chiral Ketene Acetal under Microwave Irradiation in Solvent-Free Conditions. Configurational Assignment of the Cycloadducts by NOESY Experiments and Molecular Mechanics Calculations

  摘要：

  (R)-4-Phenyl-2-methylene-1,3-dioxolane (1) undergoes 1,3-dipolar and Diels-Alder cycloadditions under microwave irradiation within 3 min with excellent yields, a simple purification procedure, and an interesting facial selectivity. The stereochemistry of these cycloadducts has been inferred by NOESY experiments and molecular mechanics calculations. X-ray structure determination was required in one case. Thermal isomerization of the cycloadducts was performed affecting only the spiro-carbon. The Diels-Alder adducts in the presence of a slight amount of acid yield the corresponding open chain esters.

  DOI：

  10.1021/jo00118a037
• 作为产物：
  描述：

  (R)-1-苯基-1,2-乙二醇 在 氢氧化钾 、 Dowex 50 (H⁺) 、 四丁基溴化铵 作用下， 反应 2.0h， 生成 (R)-2-methylene-4-phenyl-1,3-dioxolane
  参考文献：
  名称：

  外消旋和对映异构纯环烯酮缩醛的制备

  摘要：

  摘要 环烯酮缩醛已由α-卤代醛二甲基缩醛通过乙缩醛转移和随后在无溶剂条件下的PTC中消除来制备。当使用对映体纯二醇时，没有观察到外消旋化。已经研究了稳定性和储存条件。

  DOI：

  10.1080/00397919308009850

文献信息

• Determination of the Stereochemistry of Four Spirodiastereoisomers by One- and Two-Dimensional NOE Studies
  作者：A. Moreno、A. Díaz-Ortiz、E. Díez-Barra、A. de la Hoz、F. Langa、P. Prieto、T. D. W. Claridge

  DOI：10.1002/(sici)1097-458x(199601)34:1<52::aid-omr829>3.0.co;2-2

  日期：1996.1

  The stereochemistries of four cycloadducts obtained by 1,3‐dipolar reactions were investigated with one‐ and two‐dimensional NMR techniques. Analysis of a series of homonuclear NOE difference spectra and COSY and NOESY spectra recorded in a variety of solvents and at various temperatures allowed the determination of the full stereochemistry of each adduct.

  用一维和二维核磁共振技术研究了通过 1,3-偶极反应获得的四种环加合物的立体化学。在各种溶剂和各种温度下记录的一系列同核 NOE 差异光谱以及 COZY 和 NOESY 光谱的分析允许确定每个加合物的完整立体化学。
• Preparation of Racemic and Enantiomerically Pure Cyclic Ketene Acetals
  作者：A. Díaz-Ortiz、E. Díez-Barra、A. de la Hoz、P. Prieto

  DOI：10.1080/00397919308009850

  日期：1993.7

  Abstract Cyclic ketene acetals have been prepared from a-haloaldehyde dimethylacetals by transacetalization and subsequent elimination in PTC without solvent conditions. No racemization has been observed when an enantiomerically pure diol has been used. Stability and storage conditions have been studied.

  摘要 环烯酮缩醛已由α-卤代醛二甲基缩醛通过乙缩醛转移和随后在无溶剂条件下的PTC中消除来制备。当使用对映体纯二醇时，没有观察到外消旋化。已经研究了稳定性和储存条件。
• Facial Selectivity in Cycloadditions of a Chiral Ketene Acetal under Microwave Irradiation in Solvent-Free Conditions. Configurational Assignment of the Cycloadducts by NOESY Experiments and Molecular Mechanics Calculations
  作者：Angel Diaz-Ortiz、Enrique Diez-Barra、Antonio de la Hoz、Pilar Prieto、Andres Moreno、Fernando Langa、Thierry Prange、Alain Neuman

  DOI：10.1021/jo00118a037

  日期：1995.6

  (R)-4-Phenyl-2-methylene-1,3-dioxolane (1) undergoes 1,3-dipolar and Diels-Alder cycloadditions under microwave irradiation within 3 min with excellent yields, a simple purification procedure, and an interesting facial selectivity. The stereochemistry of these cycloadducts has been inferred by NOESY experiments and molecular mechanics calculations. X-ray structure determination was required in one case. Thermal isomerization of the cycloadducts was performed affecting only the spiro-carbon. The Diels-Alder adducts in the presence of a slight amount of acid yield the corresponding open chain esters.