(+/-)-1-Hydroxy-1.2.3.4.5.6.7.8-octahydro-naphthalin | 34894-66-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-1-Hydroxy-1.2.3.4.5.6.7.8-octahydro-naphthalin
• 英文别名: 1,2,3,4,5,6,7,8-Octahydro-[1]naphthol；1,2,3,4,5,6,7,8-Octahydro-1-naphthalenol；1,2,3,4,5,6,7,8-octahydronaphthalen-1-ol
• CAS: 34894-66-1
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: LJPUSAZSFVBZNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  243.5±8.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-1-Hydroxy-1.2.3.4.5.6.7.8-octahydro-naphthalin 在 VO(acetylacetone)2 chromium(VI) oxide 、 叔丁基过氧化氢 、 硫酸 、 水 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 丙酮 、 乙腈 、 苯 为溶剂， 反应 4.0h， 生成 1-oxaspiro[5.5]undecane-2,7-dione
  参考文献：
  名称：

  通过2,3-环氧醇与高价碘（III）试剂的多米诺骨反应轻松有效地合成内酯，并将其应用于内酯的合成和（+）-tanikolide的不对称合成。

  摘要：

  2,3-环氧-1-醇衍生物（即四取代的2,3-环氧-1-醇和2-或3-烷基三取代的2,3-环氧-1-醇）与PhI（OCOCF（3 ））（2）在H（2）O存在的情况下进行了详细描述。在该反应中，可以通过一次操作从2，3-环氧-1-醇衍生物直接获得几种类型的内酯衍生物。将获得的内酯依次转化为相应的内酯。该反应适用于光学活性内酯化合物的构建。通过使用该反应，已经有效地实现了抗真菌海洋天然产物（+）-tanikolide的不对称全合成。

  DOI：

  10.1002/chem.200601341
• 作为产物：
  描述：

  2-溴-1-环己烯-1-甲醛 在 indium 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 8.0h， 生成 (+/-)-1-Hydroxy-1.2.3.4.5.6.7.8-octahydro-naphthalin
  参考文献：
  名称：

  A Vinyl Radical Cyclization Route to Hydroxycyclohexene Fused Carbocycles

  摘要：

  一些羟基环己烯融合碳环衍生物是通过使用介质三正丁基锡氢化物（TBTH）和引发剂偶氮二异丁腈（AIBN）在苯回流中从6-溴-羟基-七烯-1,5-醇衍生物合成的。

  DOI：

  10.14233/ajchem.2016.19465

文献信息

• Non-dehydrative pinacol rearrangement using a Lewis acid-trialkyl orthoester combined system
  作者：Yasuyuki Kita、Yutaka Yoshida、Sachiko Mihara、Akihiro Furukawa、Kazuhiro Higuchi、Dai-Fei Fang、Hiromichi Fujioka

  DOI：10.1016/s0040-4020(98)00948-x

  日期：1998.12

  An efficient pinacol rearrangement mediated by trialkyl orthoformate has been developed. The reactions of various types of diols with a catalytic amount of a Lewis acid in the presence of an ortho ester afforded the rearranged product in good yields via a cyclic ortho ester intermediate. This combined system is applicable not only to cyclic and acyclic tri- and tetra-substituted diols but also to the

  已经开发了由原甲酸三烷基酯介导的有效频哪醇重排。在原酸酯的存在下，各种类型的二醇与催化量的路易斯酸的反应通过环状原酸酯中间体以良好的产率提供了重排产物。该组合体系不仅适用于环状和无环的三和四取代的二醇，而且适用于具有酸敏感性缩醛的二醇。
• Sn(OTf)2 as an Effective Lewis Acid in Reactions of Cyclopropyl Ketones with Acetic Anhydride: Application in the Synthesis of a 19-Nor-B-homo Steroid
  作者：Darius Paul Kranz、Aike Meier zu Greffen、Sherif El Sheikh、Jörg Martin Neudörfl、Hans-Günther Schmalz

  DOI：10.1002/ejoc.201100020

  日期：2011.5

  Attempts to convert 3β-acetoxy-5,19-cyclo-pregna-6,20-di-one (8) into a cyclocitrinol-related steroid with a bicyclo[4.4.1]-undecane AB-ring substructure through a Lewis acid-assisted fragmentation failed. Instead, treating 8 with an excess of Ac 2 O and BF 3 ·Et 2 O afforded B-homo steroid 9 in 90 % yield. This unexpected rearrangement is assumed to proceed via an intermediate bicyclobutonium cation

  尝试通过路易斯酸将 3β-乙酰氧基-5,19-cyclo-pregna-6,20-di-one (8) 转化为具有双环 [4.4.1]-十一烷 AB 环亚结构的环柠檬醇相关类固醇-辅助分片失败。相反，用过量的 Ac 2 O 和 BF 3 ·Et 2 O 处理 8 以 90% 的产率提供了 B-同型类固醇 9。这种意想不到的重排被认为是通过中间双环丁鎓阳离子进行的。值得注意的是，作为模型底物制备的三环 [4.4.1.0] undecane-1-one (rac-13) 在相同条件下没有反应。然而，通过筛选各种路易斯酸，三氟甲磺酸亚锡被确定为一种特别有效的试剂，用于在 Ac 2 O 和催化量的 Sn(OTf) 2 存在下进行环丙基酮的这种和相关的路易斯酸辅助开环反应(5 mol-%) 证明是有效的。
• On theClaisen Rearrangement of Allyl Ethyl Ketene Acetals Generatedin situ via Benzeneselenenic Acid Eliminiation
  作者：Rita Pitteloud、Martin Petrzilka

  DOI：10.1002/hlca.19790620445

  日期：1979.6.8

  alcohols 5, undergo benzeneselenenic acid elimination to transient ketene acetals 8 which afford γ, δ-unsaturated esters 9via the ester Claisen rearrangement (Scheme 2). Under the same conditions selenoxide 7h derived from benzyl alcohol 5h is converted back to benzyl alcohol with the concomitant formation of ethylphenylselenoacetate 12.

  由简单的两步法由单环和双环烯丙基醇5制备的苯硒基乙醛混合缩醛7经过苯硒酸消除，生成瞬态乙烯酮缩醛8，后者通过酯Claisen重排反应得到γ，δ-不饱和酯9 （方案2）。在相同条件下，衍生自苄醇5h的亚硒酸酯7h被转化回苄醇，并伴随形成乙基苯基硒乙酸乙酯12。
• ?Nichtcarbenoide? Zwischenstufen bei der Fragmentierung von ?-Cyclopropyltosylhydrazonen
  作者：G. Ohloff、W. Pickenhagen

  DOI：10.1002/hlca.19710540706

  日期：1971.11.1

  The sodium salts of the tricyclic tosylhydrazones 1, 4 and 5 yield by base-catalyzed fragmentation between 130–160° the monocyclic ring expansion products 2, 3 and 6. IR.-spectrometry suggests a diazoalkane A as the principal intermediate of the fragmentation. Besides the known carbene mechanism the reaction is considered to pass through a noncarbenoid intermediate.

  三环甲苯磺酰腙的钠盐1,4和5收率由碱催化的碎片130-160°之间的单环膨胀的产品2，3和6 IR.-法提出了一种重氮烷甲作为主要中间体的碎裂。除了已知的卡宾机理外，该反应还被认为通过了非卡宾类中间体。
• Dietary Protein, Phosphorus and Potassium Are Beneficial to Bone Mineral Density in Adult Men Consuming Adequate Dietary Calcium
  作者：Susan J. Whiting、Jennifer L. Boyle、Angela Thompson、Robert L. Mirwald、Robert A. Faulkner

  DOI：10.1080/07315724.2002.10719242

  日期：2002.10

  Objective: The purpose of this study was to determine relationships of calcium (Ca), protein (Pr), phosphorus (P) and potassium (K) to measures of bone mineral density in adult men.Methods: Cross-sectional analysis of 57 men ages 39 to 42 years who were participants in an ongoing study. Dietary assessment was conducted using the Block food frequency questionnaire (FFQ). BMD of total body (TB), hip and lumbar spine (LS) were measured with dual X-ray absorptiometry (DXA).Results: Ca, Pr, P and K, as well as lean body mass (LBM), showed significant correlation with BMD at the total body, hip and lumbar spine. Stepwise forward regression selection method identified LBM. height and fat mass as significant predictors of TB-BMD, LBM and height as significant predictors of hip BMD, and LBM as a significant predictor of LS-BMD. As the nutrients tested correlated significantly with each other, only one nutrient was entered into the regression model at a time to accommodate the potential for multicollinearity. In regression analysis, adjusted for site-specific anthropometric variables and energy intake, K, Pr and P intake accounted for significant (p < 0.05) prediction of TB-BNID and LS-BMD values by 7% to 13%. No bone-related nutrient added significantly to the prediction of hip BMD. Ca intake was not significantly associated with BMD at any site in the adjusted models.Conclusions: Our analysis provides support that a moderate protein 0.2 g/kg) diet, plentiful in potassium (>100 mmol/day) and phosphorus (1741 +/- 535 mg) is beneficial for maintaining bone mineral density in adult men when Ca intake was adequate (1200 +/- 515 mg).