1,2,3,4-tetrahydro-6-methyl-7-methoxy-1-naphthalenol | 61523-93-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-tetrahydro-6-methyl-7-methoxy-1-naphthalenol
• 英文别名: 1,2,3,4-tetrahydro-6-methyl-7-methoxynaphthalen-1-ol；7-methoxy-6-methyl-1,2,3,4-tetrahydronaphthalen-1-ol；7-methoxy-6-methyl-3,4-dihydro-2H-naphthalen-1-ol；7-methoxy-6-methyl-1-tetralol
• CAS: 61523-93-1
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: KRHGYKLPDFONPY-UHFFFAOYSA-N

物化性质

• 熔点：
  66.8-67.6 °C
• 沸点：
  323.4±42.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1,2,3,4-tetrahydro-6-methyl-7-methoxy-1-naphthalenol 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氯化碳 、 苯 为溶剂， 反应 4.0h， 生成 2-(bromomethyl)-3-(methoxy)naphthalene
  参考文献：
  名称：

  Photochemistry of stilbenes. 8. Eliminative photocyclization of o-methoxystilbenes

  摘要：

  DOI：

  10.1021/jo00280a032
• 作为产物：
  描述：

  2-甲基苯甲醚 在 盐酸 、 sodium tetrahydroborate 、 三氯化铝 、 汞 、 三氟乙酸酐 、 锌 作用下， 以 甲醇 、 硝基苯 、 甲苯 、 三氟乙酸 为溶剂， 反应 74.17h， 生成 1,2,3,4-tetrahydro-6-methyl-7-methoxy-1-naphthalenol
  参考文献：
  名称：

  Enzymatic resolution of α-tetralols by CALB-catalyzed acetylation

  摘要：

  A series of homochiral alpha-tetralols, as well as their respective acetates, has been obtained by esterification of racemic tetralols, using Candida antarctica lipase (CALB-Novozym(R) 435) as the biocatalyst. This enzyme is shown to be highly efficient for the kinetic resolution of the substrates studied, affording the (+)-tetralols and the (+)-acetates in excellent enantiomeric excess (up to >99%) and very good yields (>40%). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.007

文献信息

• Model Studies Toward the Synthesisof Natural Indans Utilizing a Thallium(III)-Mediated Ring-ContractionReaction
  作者：Helena M. Ferraz、Andrea M. Aguilar、Luiz F. Silva

  DOI：10.1055/s-2003-39172

  日期：——

  6-Methoxy-1-tetralone was transformed in six steps into an indan derivative related to the sesquiterpenes mutisianthol and jungianol. Key steps involve a thallium(III)-promoted ring-contraction (to assemble the indan unit) and a Wittig olefination (to attach the side chain).

  6-甲氧基-1-四氢萘酮经过六个步骤转化为与倍半萜化合物mutisianthol和jungianol相关的茨菇烷衍生物。关键步骤包括一个铊(III)催化的环收缩反应（用以组装茨菇烷单元）和一个Wittig烯化反应（用以连接侧链）。
• Introduction of a putative dopaminergic prodrug moiety into a 6,7-substitution pattern characteristic of certain 2-aminotetralin dopaminergic agonists
  作者：Joseph G. Cannon、Claire Diane True、John Paul Long、Ranbir K. Bhatnagar、Paul Leonard、Jan R. Flynn

  DOI：10.1021/jm00129a029

  日期：1989.9

  On the basis of the premise that the dopaminergic agonist profile of 2-(di-n-propylamino)-5-hydroxy-6-methyltetralin (1a) is due to in vivo oxidation of the 6-methyl moiety and that 1a may represent a novel prodrug strategy, the vicinal methyl-hydroxyl substitution pattern was incorporated into the 6- and 7-positions of 2-(di-n-propylamino)tetralin to give the 6-methyl-7-hydroxy and 6-hydroxy-7-methyl isomers 8 and 9, respectively. A multistep synthetic approach was devised which permitted preparation of target molecules 8 and 9. Pharmacological data revealed that both target compounds exhibit modest dopamine-like effects in the cardioaccelerator nerve assay in the cat, but neither appeared to be metabolically activated as was the case with 1a. The effects of 9 (but not of 8) were antagonized by pretreatment with haloperidol. Thus, the 5-hydroxy-6-methyl substitution pattern in the 2-aminotetralins remains unique as a dopaminergic agonist prodrug structure.
• Reddy, P. Anantha; Rao, G. S. Krishna, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 2, p. 100 - 103
  作者：Reddy, P. Anantha、Rao, G. S. Krishna

  DOI：——

  日期：——
• A Simple One Pot Synthesis of 1-Aryltetralins
  作者：P. Bijoy、G. S. R. Subba rao

  DOI：10.1080/00397919308011143

  日期：1993.12

  Synthesis of 1-aryltetralins is described by the Fridel-Crafts arylation of 1-tetrols with phenol.
• MALLORY, FRANK B.;RUDOLPH, M. JONATHAN;OH, SOON M., J. ORG. CHEM., 54,(1989) N9, C. 4619-4626
  作者：MALLORY, FRANK B.、RUDOLPH, M. JONATHAN、OH, SOON M.

  DOI：——

  日期：——