trans-naphthalene-1,2,3,4-tetrahydro-1,2-diol | 14211-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: trans-naphthalene-1,2,3,4-tetrahydro-1,2-diol
• 英文别名: (+/-)-trans-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene；(+/-)-trans-Tetralin-1,2-diol；(1S,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol
• CAS: 14211-53-1
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: KMQJJAOZMONGLS-UWVGGRQHSA-N

物化性质

• 熔点：
  111-112 °C
• 沸点：
  174-178 °C(Press: 12 Torr)
• 密度：
  1.260±0.06 g/cm3(Predicted)
• 保留指数：
  1535

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-naphthalene-1,2,3,4-tetrahydro-1,2-diol 在 高氯酸 作用下， 生成 (1S,2R)-cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  芳烃离子的超芳香族稳定：2-取代的1,2-二氢-1-萘酚的酸催化脱水

  摘要：

  对于酸催化脱水速率常数顺-2-取代的1,2-二氢萘由塔夫脱关系日志良好相关ķ = -0.49 - 8.8σ我，与OH和OME轻微负偏差。相比之下，反式取代基与σI的相关性较弱，并且在大多数情况下，其反应比顺式异构体慢。该行为与速率确定的2-取代碳阳离子（萘离子）中间体的形成一致，该中间体对顺式反应物具有2-CH键，其取向适合与电荷中心超共轭。对于反式异构体2-取代基本身在阳离子的最初形成的构型中定向为超共轭。有人认为，ķ顺/ ķ反式率比率的取代基（ME，8.4;卜吨，12.7; pH值，3.8; NH 3 +，160; OH，440）反映他们hyperconjugating能力相对于氢。对于已知的（RS，N 3）或怀疑的（EtSO，EtSO 2）通过π或σ邻基效应稳定阳离子的取代基，观察到反式异构体的反应更快。Taft相关性好表明顺式学生的反应正常，仅因其感应作用而有所区别。反式异构体的较

  DOI：

  10.1021/jo2020483
• 作为产物：
  描述：

  1,2,3,4-四氢-1-萘酚 在 camphor-10-sulfonic acid 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 3.0h， 生成 trans-naphthalene-1,2,3,4-tetrahydro-1,2-diol
  参考文献：
  名称：

  Verification of the Major Metabolic Oxidation Path for the Naphthoyl Group in Chemoattractant Receptor-Homologous Molecule Expressed on Th2 Cells (CRTh2) Antagonist 2-(2-(1-Naphthoyl)-8-fluoro-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)acetic Acid (Setipiprant/ACT-129968)

  摘要：

  Various racemic and enantioenriched (trans)-X,Y-dihydroxy-X,Y-dihydronaphthoyl analogues as well as X-hydroxy-naphthoyl analogues of CRTh2 antagonist 2-(2-(1-naphthoyl)-8-fluoro-3,4-dihydro-1H-pyrido [4,3-b]indol-5(2H)-yl) acetic acid (1, Setipiprant/ACT-129968) were synthesized in order to gain insight into regio- and enantioselectivity of the metabolic oxidation of 1 and to verify the structures of four metabolites that were proposed earlier in a clinical ADME study. Analytical data of the synthetic standards were compared with data from samples of biological origin. The two major metabolites M7 and M9 were unambiguously verified as 2-(2-((trans)-3,4-dihydroxy-3,4-dihydronaphthalene-1-carbony1)- and 242-((trans)-5,6-dihydroxy-5,6-dihydronaphthalene-1-carbonyl)-8-fluoro-3,4-dihydro-1H-pyrido [4,3-b]indol-5 (2H)-yl) acetic acid, respectively, each composed of two enantiomers with 68% and 44% ee in favor of (+)-(3S,4S)-M7 and (+)-(5S,6S)-M9, respectively. Likewise, minor metabolites M3 and M13 were identified as 2-(8-fluoro-2-(5-hydroxy-1-naphthoyl) and 2-(8-fluoro-2-(4-hydroxy-1-naphthoyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-5-yl)acetic acid, respectively.

  DOI：

  10.1021/acs.jmedchem.5b00824

文献信息

• Unprecedented Role of Hydronaphthoquinone Tautomers in Biosynthesis
  作者：Syed Masood Husain、Michael A. Schätzle、Steffen Lüdeke、Michael Müller

  DOI：10.1002/anie.201404560

  日期：2014.9.8

  unexpected 1,4‐diketo tautomeric form of 2‐hydroxyhydronaphthoquinone as a stable intermediate. Similar 1,4‐diketo tautomers of hydronaphthoquinones were established as products of the NADPH‐dependent enzymatic reduction of other 1,4‐naphthoquinones, and as substrates for different members of the superfamily of short‐chain dehydrogenases. We propose an essential role of hydroquinone diketo tautomers in

  醌和对苯二酚是最常见的细胞辅助因子，氧化还原介体和天然产物。在这里，我们报道了将2-羟基萘醌还原为稳定的氢萘醌的1,4-二酮互变异构形式，以及它们被真菌四羟基萘还原酶进一步还原的情况。非对映异构体和对映异构体的过量非常高，顺式-3,4-二羟基-1。四氢萘酮的高收率不包括中间氢萘醌。用NADPH和NADPD进行的标记实验证实了2-羟基氢萘醌作为稳定的中间体出乎意料的1,4-二酮互变异构形式的形成。类似的1,4-二氢萘醌的互变异构体被认为是NADPH依赖的其他1,4-萘醌的酶促还原产物，并作为短链脱氢酶超家族不同成员的底物。我们提出氢醌二酮互变异构体在生物合成和排毒过程中的重要作用。
• Microbiological transformation 32: Use of epoxide hydrolase mediated biohydrolysis as a way to enantiopure epoxides and vicinal diols: Application to substituted styrene oxide derivatives
  作者：S Pedragosa-Moreau、A Archelas、R Furstoss

  DOI：10.1016/0040-4020(96)00135-4

  日期：1996.3

  The biohydrolyses of various substituted styrene oxide derivatives using the fungi Aspergillus niger or Beauveria sulfurescens are described. The results obtained show that this methodology allows the preparation of enantiomerically enriched epoxides and diols via enantioselective and regioselective hydration. The comparative study of the results obtained suggests that these hydrolyses operate following

  描述了使用真菌黑曲霉或硫白僵菌的各种取代的苯乙烯氧化物衍生物的生物水解。获得的结果表明，该方法可以通过对映选择性和区域选择性水合制备对映体富集的环氧化物和二醇。对所得结果的比较研究表明，这些水解遵循不同的机理，并提出了相应活性位点的模型。
• Synthesis and reaction of phthaloyl peroxide derivatives, potential organocatalysts for the stereospecific dihydroxylation of alkenes
  作者：Changxia Yuan、Abram Axelrod、Michael Varela、Laura Danysh、Dionicio Siegel

  DOI：10.1016/j.tetlet.2011.03.005

  日期：2011.5

  To improve the synthesis and reactivity of phthaloyl peroxide derivatives a method has been developed using sodium percarbonate and phthaloyl chlorides. The reactions of the new phthaloyl peroxide derivatives with trans-stillbene as well as the improved reactivity of 3,4-dichlorophthaloyl peroxide with a variety of alkenes are reported.

  为了改善邻苯二甲酰过氧化物衍生物的合成和反应性，已经开发了一种使用过碳酸钠和邻苯二甲酰氯的方法。报道了新的邻苯二甲酰邻苯二甲酰衍生物与反式苯乙烯的反应，以及改进的3,4-二氯邻苯二甲酰邻苯二甲酰与各种烯烃的反应性。
• Preparation of homochiral phenolic crown ether having chiral subunits derived from (1R,2S)-cis-1,2,3,4-tetrahydronaphthalene-1,2-diol: temperature-dependent enantioselectivity in complexations with neutral amines
  作者：Koichiro Naemura、Takanori Wakebe、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/s0957-4166(97)00282-6

  日期：1997.8

  Crown ether (S,R,R,S)-1 containing chiral subunits derived from (1R,2S)-cis-1,2,3,4-tetrahydronaphthalene-1,2-diol and the phenol moiety bearing the intra-annular OH group and the 2,4-dinitrophenylazo group at its para-position have been prepared in enantiomerically pure form. The association constants for the complexes with chiral amines have been determined at various temperatures by the UV-visible

  含有衍生自（1 R，2 S）-顺式-1,2,3,4-四氢萘-1,2-二醇的手性亚基的冠醚（S，R，R，S）-1和带有内部环状OH基和对位的2,4-二硝基苯基偶氮基已经以对映体纯的形式制备。通过紫外可见光谱法测定了在各种温度下与手性胺的配合物的缔合常数，并计算了配合物形成的热力学参数。
• β-Hydroxy carbocation intermediates in solvolyses of di- and tetra-hydronaphthalene substrates
  作者：Jaya S Kudavalli、Rory A More O'Ferrall

  DOI：10.3762/bjoc.6.118

  日期：——

  the cis isomer unusually rapidly. Comparison of rates of solvolysis of 1-chloro-1,2,3,4-tetrahydronaphthalene and the corresponding (cis) substrate with a 2-hydroxy group indicates that a beta-OH slows the reaction by nearly 2000-fold, which represents a typical inductive effect characteristic also of cis-dihydrodiol substrates. The slow reaction of the trans-dihydrodiol substrate is consistent with initial

  2-甲氧基-1,2-二氢-1-萘酚的三氯乙酸酯的溶剂分解显示顺式和反式异构体之间的速率差异非常大，在乙腈水溶液中 k(cis)/k(trans) = 1800。这反映了顺式和反式萘-1,2-二氢二醇酸催化脱水形成 2-萘酚的行为，其中 k(cis)/k(trans) = 440，但与溶剂分解的行为相反四氢萘底物，1-氯-2-羟基-1,2,3,4-四氢萘，k(cis)/k(trans) = 0.5。有证据表明二氢底物的反式异构体反应异常缓慢，而不是顺式异构体反应异常迅速。1-chloro-1,2,3 的溶剂分解速率比较，4-四氢萘和带有 2-羟基的相应（顺式）底物表明，β-OH 使反应速度降低了近 2000 倍，这也代表了顺式二氢二醇底物的典型诱导效应特征。反式二氢二醇底物的缓慢反应与 β-羟基萘碳正离子的初始形成一致，其中 C-OH 占据碳正离子中心的轴向位置 β，防止通过 CH 超共轭稳