4,7-diphenylphthalide | 54537-52-9

• 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: 4,7-diphenylphthalide
• 英文别名: 4,7-diphenyl-3H-isobenzofuran-1-one；4,7-Diphenyl-1(3H)-isobenzofuranone；4,7-diphenyl-3H-2-benzofuran-1-one
• CAS: 54537-52-9
• 化学式: C₂₀H₁₄O₂
• 分子量: 286.33
• InChiKey: BTXPAHHZLQYADL-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C
• 沸点：
  556.5±50.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,7-diphenylphthalide 在 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 97.17h， 生成 5,8-diphenylnaphthalene-2,3-dicarboxylic anhydride
  参考文献：
  名称：

  4,7-Diphenylisobenzofuran:  A Useful Intermediate for the Construction of Phenyl-Substituted Acenes

  摘要：

  The formation and subsequent reactivity of previously unknown 4,7-diphenylisobenzofuran, 5, is reported. The Diels-Alder reaction between 5 and p-benzoquinone in boiling glacial acetic acid yields an unprecedented exo,exo anti dual cycloaddition product, 16b, in excellent yield and with 100% diastereoselectivity. Differences between the reactivities of 5 and the more common 1,3-diphenylisobenzofuran are highlighted. Reactive 5 is utilized to form new three-, four-, and five-ring acenes, and the latter compound is reacted with [60]fullerene to produce new [60]fullerene-acene adducts.

  DOI：

  10.1021/jo062675b
• 作为产物：
  描述：

  1,4-二苯基-1,3丁二烯 在 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 锌 作用下， 以 甲苯 、 xylene 为溶剂， 反应 50.0h， 生成 4,7-diphenylphthalide
  参考文献：
  名称：

  4,7-Diphenylisobenzofuran:  A Useful Intermediate for the Construction of Phenyl-Substituted Acenes

  摘要：

  The formation and subsequent reactivity of previously unknown 4,7-diphenylisobenzofuran, 5, is reported. The Diels-Alder reaction between 5 and p-benzoquinone in boiling glacial acetic acid yields an unprecedented exo,exo anti dual cycloaddition product, 16b, in excellent yield and with 100% diastereoselectivity. Differences between the reactivities of 5 and the more common 1,3-diphenylisobenzofuran are highlighted. Reactive 5 is utilized to form new three-, four-, and five-ring acenes, and the latter compound is reacted with [60]fullerene to produce new [60]fullerene-acene adducts.

  DOI：

  10.1021/jo062675b

文献信息

• Ring-chain tautomerism as a factor in the reaction between Grignard reagents and substituted phthalides
  作者：J.G. Smith、R.T. Wikman

  DOI：10.1016/s0040-4020(01)97419-8

  日期：1974.1

  With phthalide two equivalents of Grignard reagent react rapidly in a reaction which could not be controlled to give stepwise addition. In contrast, 3,3- and 4,7-disubstituted phthalides react with only one equivalent of organometallic reagent. The primary addition product formed from one equivalent each of phthalide and Grignard reagent exists in a ring-chain tautomerism whose position is controlled

  与邻苯二甲酰亚胺一起，当量的格氏试剂的两个当量在无法控制的逐步反应中迅速反应。相反，3，3-和4，7-二取代的邻苯二甲酸酯仅与一当量的有机金属试剂反应。由一当量的邻苯二甲酸酯和格氏试剂形成的一次加成产物存在于环链互变异构中，其位置由邻苯二甲酰胺中存在的取代基与格氏试剂引入的烷基之间的相互作用控制。对于取代的邻苯二甲酸酯，这些相互作用阻止了主要加成产物的开环，因此第二当量的格氏试剂不发生反应。在不存在取代基的情况下，发生开环和第二当量的反应。
• Furan-2(3H)- and -2(5H)-ones. Part 8.1 Conformation and di-π-methane reactivity of the 4,7-disubstituted tetrahydroisobenzofuran-1-one system: a mechanistic and exploratory study
  作者：Osamu Muraoka、Genzoh Tanabe、Emi Yamamoto、Masaru Ono、Toshie Minematsu、Takayoshi Kimura

  DOI：10.1039/a702108i

  日期：——

  that the molecular energy difference between the planar structure and the boat conformation is small enough for a boat–planar–boat conversion. On the basis of the calculations, the di-π-methane rearrangement of the compounds 14 and 15 is supposed to proceed via the boat conformation with a pseudoaxial phenyl substituent. An X-ray structure determination of the two diphenyl substrates cis- and trans-14

  的光照射顺式-和反式-4,7-二苯基- 1,3,4,7四氢异苯并呋喃-1-酮的顺式-和反式-14和其4-甲基类似物顺式-和反式-15，得到相应的二- π -甲烷重排产物27、28和24，产率中等。MM2计算顺式和反式-4,7-二苯基底物顺式和反式-14表明，这两种化合物的平面结构都是最稳定的，并且该平面结构与船形之间的分子能差很小，足以进行船-平面-船转换。基于这些计算，化合物14和15的二-π-甲烷重排被认为是通过具有伪轴向苯基取代基的舟状构型进行的。两个联苯底物顺式和反式-14的X射线结构测定为预测顺式和反式二取代的四氢异苯并呋喃酮的最佳结构的计算有效性提供了有力的支持。