2-methoxy-4,5-diphenylphenol | 96250-86-1

• 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: 2-methoxy-4,5-diphenylphenol
• CAS: 96250-86-1
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: NRDIEIJSIHCVHU-UHFFFAOYSA-N

物化性质

• 熔点：
  146-148 °C(Solv: dichloromethane (75-09-2); methanol (67-56-1))
• 沸点：
  403.3±45.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxy-4,5-diphenylphenol 在 苯亚硒酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以61%的产率得到4,5-diphenyl-1,2-benzoquinone
  参考文献：
  名称：

  天然存在的三联苯醌的结构研究。

  摘要：

  合成了两个三联苯醌，用于对天然存在的生物活性三联苯醌的结构研究。Suzuki-Miyaura偶联并随后氧化生成的取代苯酚，合成了3-甲氧基-5,6-二苯基环己-3,5-二烯1,2-二酮，这是我们对NMR光谱分析提出的一种可能的结构，尽管与天然产品不同。从市售的2,5-二苯基-1,4-苯醌分三步合成了最近分离出的3-甲氧基-2,5-二苯基环己-2,5-二烯-1,4-二酮，总收率良好，并且它的NMR谱图与天然产物的谱图相同。

  DOI：

  10.1271/bbb.130199
• 作为产物：
  描述：

  2-methoxy-4,4-diphenylcyclohexa-2,5-dien-1-one 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以63%的产率得到2-methoxy-4,5-diphenylphenol
  参考文献：
  名称：

  Electronic and Steric Effects in the Dienone-Phenol Rearrangement of 2-Hydroxy- and 2-Alkoxycyclohexa-2,5-dien-1-ones

  摘要：

  A series of 4,4,6-trisubstituted-2-hydroxy- and -2-alkoxycyclohexa-2,5-dien-1-ones (7 and 8) were prepared, where the substituent at C-6 was H, CH3, Ph, tert-butyl, or Oft. In the acid-catalyzed dienone-phenol rearrangement of 7 and 8, the C-4 substituent migrates regioselectively to C-5, completely shunning the enol double bond, even though the substituents at C-6 are substantially larger than the OH or OMe groups situated at C-2. The C-5 regioselectivity in hydroxy dienones 7a-f and 8a,b, as well as the decreased rate of reaction in the case of dienone 7g, can be simply rationalized by considering the relative electron density at C-3 vs C-5 in the protonated form of ? or 8. Our results clearly indicate that the regioselectivity of the dienone-phenol rearrangement in these enolic systems is completely controlled by the electronic factors, which far outweigh any steric considerations.

  DOI：

  10.1021/jo00086a038

文献信息

• Matoba, Katsuhide; Kawagoshi, Fujiko; Yamazaki, Takao, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 12, p. 4721 - 4725
  作者：Matoba, Katsuhide、Kawagoshi, Fujiko、Yamazaki, Takao

  DOI：——

  日期：——
• Matoba, Katsuhide; Kawagoshi, Fujiko; Tanabe, Minoko, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 9, p. 3709 - 3714
  作者：Matoba, Katsuhide、Kawagoshi, Fujiko、Tanabe, Minoko、Yamazaki, Takao

  DOI：——

  日期：——
• MATOBA, KATSUHIDE;KAWAGOSHI, FUJIKO;TANABE, MINAKO;YAMAZAKI, TAKAO, CHEM. AND PHARM. BULL., 1985, 33, N 9, 3709-3714
  作者：MATOBA, KATSUHIDE、KAWAGOSHI, FUJIKO、TANABE, MINAKO、YAMAZAKI, TAKAO

  DOI：——

  日期：——
• Structural Study on a Naturally Occurring Terphenyl Quinone
  作者：Atsuo NAKAZAKI、Wen-Yu HUANG、Kazushi KOGA、Boon-ek YINGYONGNARONGKUL、Jutatip BOONSOMBAT、Yusuke SAWAYAMA、Takashi TSUJIMOTO、Toshio NISHIKAWA

  DOI：10.1271/bbb.130199

  日期：2013.7.23

  Two terphenyl quinones were synthesized for a structural study on a naturally occurring biologically active terphenyl quinone. 3-Methoxy-5,6-diphenylcyclohexa-3,5-dien-1,2-dione, a possible structure proposed by our analysis of the NMR spectra, was synthesized by Suzuki-Miyaura coupling and subsequent oxidation of the resulting substituted phenol, although not being identical to the natural product

  合成了两个三联苯醌，用于对天然存在的生物活性三联苯醌的结构研究。Suzuki-Miyaura偶联并随后氧化生成的取代苯酚，合成了3-甲氧基-5,6-二苯基环己-3,5-二烯1,2-二酮，这是我们对NMR光谱分析提出的一种可能的结构，尽管与天然产品不同。从市售的2,5-二苯基-1,4-苯醌分三步合成了最近分离出的3-甲氧基-2,5-二苯基环己-2,5-二烯-1,4-二酮，总收率良好，并且它的NMR谱图与天然产物的谱图相同。
• Electronic and Steric Effects in the Dienone-Phenol Rearrangement of 2-Hydroxy- and 2-Alkoxycyclohexa-2,5-dien-1-ones
  作者：Aryeh A. Frimer、Vered Marks、Milon Sprecher、Pessia Gilinsky-Sharon

  DOI：10.1021/jo00086a038

  日期：1994.4

  A series of 4,4,6-trisubstituted-2-hydroxy- and -2-alkoxycyclohexa-2,5-dien-1-ones (7 and 8) were prepared, where the substituent at C-6 was H, CH3, Ph, tert-butyl, or Oft. In the acid-catalyzed dienone-phenol rearrangement of 7 and 8, the C-4 substituent migrates regioselectively to C-5, completely shunning the enol double bond, even though the substituents at C-6 are substantially larger than the OH or OMe groups situated at C-2. The C-5 regioselectivity in hydroxy dienones 7a-f and 8a,b, as well as the decreased rate of reaction in the case of dienone 7g, can be simply rationalized by considering the relative electron density at C-3 vs C-5 in the protonated form of ? or 8. Our results clearly indicate that the regioselectivity of the dienone-phenol rearrangement in these enolic systems is completely controlled by the electronic factors, which far outweigh any steric considerations.