ethyl 1-hydroxy-4-phenylnaphthalene-3-carboxylate | 675125-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 1-hydroxy-4-phenylnaphthalene-3-carboxylate
• 英文别名: 4-hydroxy-1-phenyl-2-naphthoic acid ethyl ester；4-hydroxy-1-phenyl-[2]naphthoic acid ethyl ester；4-Hydroxy-1-phenyl-[2]naphthoesaeure-aethylester；Ethyl 4-hydroxy-1-phenyl-2-naphthoate；ethyl 4-hydroxy-1-phenylnaphthalene-2-carboxylate
• CAS: 675125-42-5
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: BLPNMUARXCORPX-UHFFFAOYSA-N

物化性质

• 熔点：
  231.5-232.5 °C
• 沸点：
  482.9±33.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  ethyl 1-hydroxy-4-phenylnaphthalene-3-carboxylate 生成 1-phenyl-4-hydroxy-2-naphthoic acid
  参考文献：
  名称：

  Gliotoxin. V. The Structure of Certain Indole Derivatives Related to Gliotoxin^1,2

  摘要：

  DOI：

  10.1021/ja01219a023
• 作为产物：
  描述：

  乙醇 、 ethyl 4-acetoxy-1-phenyl-2-naphthoate 在 盐酸 作用下， 生成 ethyl 1-hydroxy-4-phenylnaphthalene-3-carboxylate
  参考文献：
  名称：

  Gliotoxin. V. The Structure of Certain Indole Derivatives Related to Gliotoxin^1,2

  摘要：

  DOI：

  10.1021/ja01219a023

文献信息

• Synthesis and Photochromism of Novel Phenylene-Linked Photochromic Bispyrans
  作者：Weili Zhao、Erick M. Carreira

  DOI：10.1021/ol052587y

  日期：2006.1.1

  [reaction: see text] Phenylene-linked bisnaphthopyrans were synthesized in good yields via the one-pot reaction of bis-propargyl alcohols with naphthols. Temperature-dependent photochromism in 1,4-phenylene-linked bispyrans leads to up to 60 nm bathochromic shift between the colored species formed at room temperature and at -20 degrees C. Better fatigue resistance and higher colorability was observed

  [反应：见正文]通过双炔丙基醇与萘酚的一锅反应以高收率合成了苯连接的双萘并吡喃。1,4-亚苯基连接的双吡喃中随温度变化的光致变色现象导致在室温和-20摄氏度下形成的有色物质之间出现高达60 nm的红移。在1,4-亚苯基中观察到更好的抗疲劳性和更高的可着色性与1，3-亚苯基连接的双-[2H]-萘并[1,2-b]吡喃相比，双-[2H]-萘并[1,2-b]吡喃。
• Facile One-Pot Synthesis of Photochromic Pyrans
  作者：Weili Zhao、Erick M. Carreira

  DOI：10.1021/ol035599x

  日期：2003.10.1

  [reaction: see text]. Photochromic pyrans, including [3H]naphtho[2,1-b]pyrans, [2H]naphtho[1,2-b]pyrans, indeno-fused naphtho[1,2-b]pyrans, and heteroannulated pyrans, were synthesized in excellent yields through a facile one-pot procedure by reaction of propargyl alcohol and naphthol or phenol derivatives in the presence of 5 mol % PPTS and 2 equiv of (MeO)3CH. Symmetrical and nonsymmetrical bispyrans

  [反应：请参见文字]。合成了包括[3H]萘[2,1-b]吡喃，[2H]萘[1,2-b]吡喃，茚并稠合的萘[1,2-b]吡喃和异环吡喃的光致变色吡喃。在5 mol％PPTS和2当量（MeO）3CH存在下，通过炔丙醇与萘酚或苯酚衍生物反应，通过简便的一锅法获得优异的收率。对称和非对称双吡喃也可以使用该方案制备。
• Synthesis and sequential photochromism of thiophene-linked bis-pyrans
  作者：Xiuhong Lu、Qian Dong、Xiaochun Dong、Weili Zhao

  DOI：10.1016/j.tet.2015.04.068

  日期：2015.6

  Novel bis[3H]-naphtho[2,1-b]pyrans 1a-1g and bis[2H]-naphtho[1,2-b]pyrans 2a-2g were prepared efficiently. Such thiophene-linked bispyrans display distinct color change under continuous UV irradiation with up to 110 am of bathochromic shift between the finally generated colored forms and initially generated forms. They also show high colorability, as well as good fatigue-resistance. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and photochromic properties of spiro[naphthopyran-7′H-benzocyclohepta-5′,8′-dienes]
  作者：Daniel L. Crossley、Christopher D. Gabbutt、B. Mark Heron、Paul Kay、Martin Mogstad

  DOI：10.1016/j.dyepig.2012.03.031

  日期：2012.10

  A series of spironaphthopyrans has been synthesised by the acid-catalysed condensation between either a substituted 1-naphthol or 2-naphthol and the propargylic alcohol derived from the addition of lithium trimethylsilylacetylide to a 7H-benzocycloheptan-7-one with subsequent in situ silyl group removal. The photochromism of the novel spironaphthopyrans was characterised by a bathochromically shifted lambda(max) coupled with a relatively quick initial fade of the photogenerated species relative to the comparable diphenyl substituted model compounds. After initial fading a relatively intense residual colour persisted for the spironaphthopyrans. (C) 2012 Elsevier Ltd. All rights reserved.