4-[Bis(4-methylphenyl)methylidene]-2,6-di(propan-2-yl)cyclohexa-2,5-dien-1-one | 1357059-73-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-[Bis(4-methylphenyl)methylidene]-2,6-di(propan-2-yl)cyclohexa-2,5-dien-1-one
• 英文别名: 4-[bis(4-methylphenyl)methylidene]-2,6-di(propan-2-yl)cyclohexa-2,5-dien-1-one
• CAS: 1357059-73-4
• 化学式: C₂₇H₃₀O
• 分子量: 370.535
• InChiKey: OEOQWHRCLRYJDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4,4'-二甲基二苯甲酮 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 硫酸 、 溶剂黄146 作用下， 以 甲醇 、 苯 为溶剂， 反应 12.0h， 生成 4-[Bis(4-methylphenyl)methylidene]-2,6-di(propan-2-yl)cyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  Chiral and Racemic Tetramorphs of 2,6-Di-t-Butylditolylfuchsone

  摘要：

  The title molecule 4-(alpha,alpha-ditolylmethylene)-2,6-di-t-butyl-1,4-benzoquinone (abbreviated as di-t-butylditolylfuchsone and numbered 2-t-Bu) serendipitously afforded four concomitant polymorphs during routine purification by column chromatography in the same solvent elution fraction. Polymorph I crystallized in chiral space group P2(1). Polymorphs II, III, and IV crystallized in centrosymmetric space groups P2(1)/n, Pbca, and C2/c, respectively. The role of bulky t-Bu groups for crystallization in the chiral space group is discussed for 2,6-ditolyl and 2,6-diphenyl fuchsones, alpha,alpha-Diphenylmethylene-2,6di-t-butyl-1,4-benzoquinone (di-t-butyldiphenylfuchsone, 1-t-Bu) crystallized in P2(1) (one polymorph) and P2(1)/c (two polymorphs) space groups. Unfavorable steric repulsions due to bulky t-Bu groups result in voids in the crystal structures of centrosynametric polymorphs II and III. Phase transformation of racemic structure II to III and finally to chiral polymorph I was monitored by thermal microscopy and differential scanning calorimetry. X-ray diffraction confirmed the phase transformation to be a single-crystal-tosingle-crystal event. The chiral polyrnorph I is the stable modification in the tetramorphic system. Several randomly picked single crystals of 2-t-Bu polymorph I had the same absolute chirality by circular dichroism spectroscopy. A new molecule capable of exhibiting conformational chirality via atropisomerism is identified.

  DOI：

  10.1021/cg201652h

文献信息

• Chiral and Racemic Tetramorphs of 2,6-Di-<i>t</i>-Butylditolylfuchsone
  作者：Naba K. Nath、Sanjay Nilapwar、Ashwini Nangia

  DOI：10.1021/cg201652h

  日期：2012.3.7

  The title molecule 4-(alpha,alpha-ditolylmethylene)-2,6-di-t-butyl-1,4-benzoquinone (abbreviated as di-t-butylditolylfuchsone and numbered 2-t-Bu) serendipitously afforded four concomitant polymorphs during routine purification by column chromatography in the same solvent elution fraction. Polymorph I crystallized in chiral space group P2(1). Polymorphs II, III, and IV crystallized in centrosymmetric space groups P2(1)/n, Pbca, and C2/c, respectively. The role of bulky t-Bu groups for crystallization in the chiral space group is discussed for 2,6-ditolyl and 2,6-diphenyl fuchsones, alpha,alpha-Diphenylmethylene-2,6di-t-butyl-1,4-benzoquinone (di-t-butyldiphenylfuchsone, 1-t-Bu) crystallized in P2(1) (one polymorph) and P2(1)/c (two polymorphs) space groups. Unfavorable steric repulsions due to bulky t-Bu groups result in voids in the crystal structures of centrosynametric polymorphs II and III. Phase transformation of racemic structure II to III and finally to chiral polymorph I was monitored by thermal microscopy and differential scanning calorimetry. X-ray diffraction confirmed the phase transformation to be a single-crystal-tosingle-crystal event. The chiral polyrnorph I is the stable modification in the tetramorphic system. Several randomly picked single crystals of 2-t-Bu polymorph I had the same absolute chirality by circular dichroism spectroscopy. A new molecule capable of exhibiting conformational chirality via atropisomerism is identified.