3,5,8-triphenyl-3H-naphtho[2,3-c]furan-1-one | 936699-28-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3,5,8-triphenyl-3H-naphtho[2,3-c]furan-1-one
• 英文别名: 1,5,8-triphenyl-1H-benzo[f][2]benzofuran-3-one
• CAS: 936699-28-4
• 化学式: C₃₀H₂₀O₂
• 分子量: 412.488
• InChiKey: ITCDLWSKJQLLQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 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：

  3,5,8-triphenyl-3H-naphtho[2,3-c]furan-1-one 、 phenylmagnesium bromide 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以67%的产率得到1,3,5,8-tetraphenyl-1,3-dihydro-naphtho[2,3-c]furan-1-ol
  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 sodium hydroxide 、 sodium tetrahydroborate 、 三氯化铝 、 二异丁基氢化铝 、 对甲苯磺酸 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 锌 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 、 xylene 为溶剂， 反应 311.17h， 生成 3,5,8-triphenyl-3H-naphtho[2,3-c]furan-1-one
  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

• 4,7-Diphenylisobenzofuran:  A Useful Intermediate for the Construction of Phenyl-Substituted Acenes
  作者：James Eric Rainbolt、Glen P. Miller

  DOI：10.1021/jo062675b

  日期：2007.4.1

  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.