(R,R)-(+)-4,5-di(4-methylphenyl)-1,3-dioxolanone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R,R)-(+)-4,5-di(4-methylphenyl)-1,3-dioxolanone
• 英文别名: (4R,5R)-4,5-bis(4-methylphenyl)-1,3-dioxolan-2-one
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: NRLUPESZZQCNQH-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,4'-二甲基-反-二苯乙烯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (R,R)-(+)-4,5-di(4-methylphenyl)-1,3-dioxolanone
  参考文献：
  名称：

  Induction of Cholesteric Mesophases by Simple Cyclic Derivatives of p,p‘-Disubstituted 1,2-Diphenylethane-1,2-diols:  Importance of Shape and Polarizability Effects

  摘要：

  A systematic study of the cholesteric induction in nematic solvents (MBBA and E7) by some cyclic derivatives of unsubstituted and p,p'-disubstituted-1,2-diphenylethane-1, shows that the values of the twisting power are significantly dependent on the nature of the link connecting the two oxygen atoms and on the nature of the p,p'-substituents. This result has been interpreted considering that the nature of the bridge affects the overall molecular shape and the p,p'-substituents affect both the molecular polarizability and shape. This investigation points out that the polarizability of the solute and the solvent is the main parameter in determining the value of the twisting power while electrostatic arene-arene interactions contribute to a less extent. It has been also observed that solutes having the same structure and the same absolute configuration can induce cholesteric helix of opposite sign depending on the substituent on the aromatic ring. This finding indicates that configurational assignments by cholesteric induction are reliable only if high values of twisting power are measured.

  DOI：

  10.1021/jo990038y

文献信息

• Novel cyclization of dimeric dianions of anils or aldehydes with triphosgene: A safe and efficient synthesis of substituted imidazolidin-2-ones and 4,5-diaryl-1,3-dioxolan-2-ones
  作者：Zhifang Li、Yongmin Zhang

  DOI：10.1002/hc.10065

  日期：——

  The reaction of Schiff bases or aldehydes with samarium diiodide in dry THF, followed by addition of triphosgene, gives substituted imidazolidin-2-ones and 4,5-diaryl–1,3-dioxolan-2-ones, respectively, in moderate to good yields under mild conditions. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:46–49, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10065

  席夫碱或醛与二碘化钐在干燥的 THF 中反应，然后加入三光气，分别得到取代的咪唑啉-2-酮和 4,5-二芳基-1,3-二氧戊环-2-酮，中等至良好温和条件下的产量。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:46–49, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10065
• Induction of Cholesteric Mesophases by Simple Cyclic Derivatives of <i>p,p</i><i>‘</i>-Disubstituted 1,2-Diphenylethane-1,2-diols:  Importance of Shape and Polarizability Effects
  作者：Stefano Superchi、Maria Irene Donnoli、Gloria Proni、Gian Piero Spada、Carlo Rosini

  DOI：10.1021/jo990038y

  日期：1999.6.1

  A systematic study of the cholesteric induction in nematic solvents (MBBA and E7) by some cyclic derivatives of unsubstituted and p,p'-disubstituted-1,2-diphenylethane-1, shows that the values of the twisting power are significantly dependent on the nature of the link connecting the two oxygen atoms and on the nature of the p,p'-substituents. This result has been interpreted considering that the nature of the bridge affects the overall molecular shape and the p,p'-substituents affect both the molecular polarizability and shape. This investigation points out that the polarizability of the solute and the solvent is the main parameter in determining the value of the twisting power while electrostatic arene-arene interactions contribute to a less extent. It has been also observed that solutes having the same structure and the same absolute configuration can induce cholesteric helix of opposite sign depending on the substituent on the aromatic ring. This finding indicates that configurational assignments by cholesteric induction are reliable only if high values of twisting power are measured.