1-iodo-8-(4-methoxyphenyl)naphthalene | 1374400-53-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-iodo-8-(4-methoxyphenyl)naphthalene
• CAS: 1374400-53-9
• 化学式: C₁₇H₁₃IO
• 分子量: 360.194
• InChiKey: RGSYJWVCCAJGRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-iodo-8-(4-methoxyphenyl)naphthalene 在 4-甲基苯磺酸吡啶 、 三溴化硼 、 铜 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 6-(8-(2,3,4,5,6-pentafluorophenyl)naphthalen-1-yl)-2,2-diphenyl-2H-chromene
  参考文献：
  名称：

  Through-Space Control of the Persistence of Photogenerated o-Quinonoid Intermediates in Naphthalenes Containing Cofacially Oriented Chromenes and Arenes

  摘要：

  Remarkable modulation of the persistence of the photogenerated colored o-quinonoid intermediates via a through-space interaction has been demonstrated in chromenes 1-4 based on 1,8-diarylnaphthalenes. Polar/pi interaction is shown to stabilize the closed form of 4 to such an extent that photoinduced coloration is virtually invisible, while the same stabilization in the opened form of 2 permits ready coloration with a long-lived o-quinonoid intermediate.

  DOI：

  10.1021/ol300449p
• 作为产物：
  描述：

  1,8-二氨基萘 在 盐酸 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 34.0h， 生成 1-iodo-8-(4-methoxyphenyl)naphthalene
  参考文献：
  名称：

  Through-Space Control of the Persistence of Photogenerated o-Quinonoid Intermediates in Naphthalenes Containing Cofacially Oriented Chromenes and Arenes

  摘要：

  Remarkable modulation of the persistence of the photogenerated colored o-quinonoid intermediates via a through-space interaction has been demonstrated in chromenes 1-4 based on 1,8-diarylnaphthalenes. Polar/pi interaction is shown to stabilize the closed form of 4 to such an extent that photoinduced coloration is virtually invisible, while the same stabilization in the opened form of 2 permits ready coloration with a long-lived o-quinonoid intermediate.

  DOI：

  10.1021/ol300449p

文献信息

• Pd‐Catalyzed Annulation of 1‐Halo‐8‐arylnaphthalenes and Alkynes Leading to Heptagon‐Embedded Aromatic Systems
  作者：Jianming Yan、Md. Shafiqur Rahman、Naohiko Yoshikai

  DOI：10.1002/chem.201805746

  日期：2019.7.17

  A palladium‐catalyzed heptagon‐forming annulation reaction between 1‐halo‐8‐arylnaphthalene and diarylacetylene is reported. The reaction is promoted using a catalytic system comprised of Pd(OAc)2, moderately electron‐deficient triarylphosphine P(4‐ClC6H4)3, and Ag2CO3 to afford benzo[4,5]cyclohepta[1,2,3‐de]naphthalene derivatives in moderate to good yields, in preference to fluoranthene as a competing

  据报道，1-卤代-8-芳基萘与二芳基乙炔之间存在钯催化的七边形环化反应。使用由Pd（OAc）2，中度缺电子的三芳基膦P（4-ClC 6 H 4）3和Ag 2 CO 3组成的催化体系促进反应，得到苯并[4,5]环庚[1,2 ，3-德在中度至良好的产率]萘衍生物，优先于荧蒽作为竞争副产物。也可以实现双重环化，以获取一种新型的嵌入七边形的多环芳烃化合物。