phenyl 4-hydroxy-2-naphthalenecarboxylate | 1572509-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: phenyl 4-hydroxy-2-naphthalenecarboxylate
• 英文别名: Phenyl 4-hydroxynaphthalene-2-carboxylate；phenyl 4-hydroxynaphthalene-2-carboxylate
• CAS: 1572509-50-2
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: MVCKRCUDDKUSSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenyl 4-hydroxy-2-naphthalenecarboxylate 在 sodium azide 、 2-chloro-1,3-dimethyl imidazolium chloride 、 15-冠醚-5 、 palladium diacetate 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.33h， 生成 phenyl 2,3,4,5-tetrahydronaphtho[1,2-b][1,4]dioxocine-7-carboxylate
  参考文献：
  名称：

  Pd(OAc)₂-Catalyzed Macrocyclization of 1,2-Diazonaphthoquinones with Cyclic Ethers

  摘要：

  Pd(OAc)(2) was found to be an efficient catalyst for the macrocyclization of 1,2-diazonaphthoquinones and cyclic ethers. This transformation serves as an efficient method for the synthesis of protected 1,2-naphthalenediols.

  DOI：

  10.1021/ol500222s
• 作为产物：
  描述：

  4-羟基萘-2-羧酸甲酯 在 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 水 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 20.0h， 生成 phenyl 4-hydroxy-2-naphthalenecarboxylate
  参考文献：
  名称：

  Rh-Catalyzed Cyclization of 3-Aryloxycarbonyldiazonaphthoquinones for the Synthesis of β-Phenylnaphthalene Lactones and Formal Synthesis of Pradimicinone

  摘要：

  In this study, we developed a novel method for the synthesis of beta-phenylnaphthalene lactones. The diazo-transfer reactions of 2-azido-1,3-dimethylimidazolinium chlorides to 3-aryloxycarbonyl-1-naphthols proceeded smoothly to give corresponding 3-aryloxycarbonyldiazonaphthoquinones in high yields. These intermediates were further transformed to beta-phenylnaphthalene lactones through a Rh-catalyzed intramolecular formal C-H insertion reaction. This method of lactone formation was efficiently applied to the formal total synthesis of pradimicinone.

  DOI：

  10.1021/acs.joc.5b01251

文献信息

• Rh(II)-catalyzed formal [3+3] cycloaddition of diazonaphthoquinones and propargyl alcohols: Synthesis of 2,3-dihydronaphtho-1,4-dioxin derivatives
  作者：Mitsuru Kitamura、Tomoaki Nishimura、Kota Otsuka、Hirokazu Shimooka、Tatsuo Okauchi

  DOI：10.1016/j.tetlet.2020.151853

  日期：2020.5

  A Rh(II)-catalyzed formal [3+3] cyclization of diazonaphthoquinones and propargyl alcohol is reported to afford 2,3-dihydro-1,4-benzodioxins. Various terminal propargyl alcohols react with diazonapthoquinone in the presence of Rh2(OAc)4 to give the corresponding dihydrodioxins in good to high yields. However, dihydrodioxins are not formed in the reaction of internal propargyl alcohols, and the O–H

  据报道，Rh（II）催化的重氮萘醌和炔丙醇的正式[3 + 3]环化反应可提供2,3-二氢-1,4-苯并二恶英。各种末端炔丙醇在Rh 2（OAc）4的存在下与重氮萘醌反应，以高至高收率得到相应的二氢二恶英。但是，在内部炔丙醇的反应中不会形成二氢二恶英，取决于末端取代基，OH插入产物和2,5-二氢呋喃是主要产物。提出通过Rh（II）催化的分子间氧鎓叶立德形成和随后的内部炔基6- exo - dig环化反应形成2,3-二氢-1,4-苯并二恶英。
• Rh-Catalyzed Cyclization of 3-Aryloxycarbonyldiazonaphthoquinones for the Synthesis of β-Phenylnaphthalene Lactones and Formal Synthesis of Pradimicinone
  作者：Mitsuru Kitamura、Shuhei Takahashi、Tatsuo Okauchi

  DOI：10.1021/acs.joc.5b01251

  日期：2015.8.21

  In this study, we developed a novel method for the synthesis of beta-phenylnaphthalene lactones. The diazo-transfer reactions of 2-azido-1,3-dimethylimidazolinium chlorides to 3-aryloxycarbonyl-1-naphthols proceeded smoothly to give corresponding 3-aryloxycarbonyldiazonaphthoquinones in high yields. These intermediates were further transformed to beta-phenylnaphthalene lactones through a Rh-catalyzed intramolecular formal C-H insertion reaction. This method of lactone formation was efficiently applied to the formal total synthesis of pradimicinone.
• Pd(OAc)₂-Catalyzed Macrocyclization of 1,2-Diazonaphthoquinones with Cyclic Ethers
  作者：Mitsuru Kitamura、Masato Kisanuki、Koichi Kanemura、Tatsuo Okauchi

  DOI：10.1021/ol500222s

  日期：2014.3.21

  Pd(OAc)(2) was found to be an efficient catalyst for the macrocyclization of 1,2-diazonaphthoquinones and cyclic ethers. This transformation serves as an efficient method for the synthesis of protected 1,2-naphthalenediols.