(+/-)-1,2,3,4-tetrahydro-4-phenanthrenol | 56179-82-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (+/-)-1,2,3,4-tetrahydro-4-phenanthrenol
• 英文别名: 1,2,3,4-Tetrahydrophenanthren-1-ol；1,2,3,4-tetrahydrophenanthren-4-ol；1-Hydroxy-1,2,3,4-tetrahydrophenanthren；1,2,3,4-Tetrahydrophenanthrene-4-ol
• CAS: 56179-82-9
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: XATSUTOXPXWMRG-UHFFFAOYSA-N

物化性质

• 熔点：
  130.5-132 °C
• 沸点：
  385.3±11.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (+/-)-1,2,3,4-tetrahydro-4-phenanthrenol 在 盐酸 、 溶剂黄146 作用下， 生成 1,2-二氢菲
  参考文献：
  名称：

  一些氢菲的 13 C NMR 谱的修正分配

  摘要：

  报告了五种氢菲衍生物的 13C 和 1H NMR 化学位移分配。错误的文献分配已得到纠正。

  DOI：

  10.1002/mrc.1260270813
• 作为产物：
  描述：

  4-(2-萘基)丁酰氯 在 sodium tetrahydroborate 、 四氯化锡 作用下， 以 甲醇 、 苯 为溶剂， 生成 (+/-)-1,2,3,4-tetrahydro-4-phenanthrenol
  参考文献：
  名称：

  一些氢菲的 13 C NMR 谱的修正分配

  摘要：

  报告了五种氢菲衍生物的 13C 和 1H NMR 化学位移分配。错误的文献分配已得到纠正。

  DOI：

  10.1002/mrc.1260270813

文献信息

• Tandem Oxidative Ring-Opening/Cyclization Reaction in Seconds in Open Atmosphere for the Synthesis of 1-Tetralones in Water–Acetonitrile
  作者：Jingxian Fang、Lesong Li、Chu Yang、Jinping Chen、Guo-Jun Deng、Hang Gong

  DOI：10.1021/acs.orglett.8b03246

  日期：2018.11.16

  A mild and practical tandem oxidative ring-opening/cyclization reaction mediated by Ce4+ for the synthesis of 1-tetralones is presented. This rapid transformation was completed within 30 s and conducted in an open reactor at 0 °C in a water–acetonitrile mixture. Various cyclobutanol derivatives are transformed into desired products in good to high yields, and this reaction can be easily scaled up to

  提出了一种温和且实用的由Ce 4+介导的串联氧化开环/环化反应，用于合成1-tetralones。快速转变在30 s内完成，并在0°C的开放式反应器中于水-乙腈混合物中进行。各种环丁醇衍生物都可以高收率或高收率转化为所需的产物，并且该反应可以轻松放大至克级。
• Iodine Monochloride-Amine Complexes: An Experimental and Computational Approach to New Chiral Electrophiles
  作者：Jürgen Haas、Stewart Bissmire、Thomas Wirth

  DOI：10.1002/chem.200500507

  日期：2005.9.19

  Lactonizations are important steps in many synthetic sequences. Substrate-controlled reactions that use chiral auxiliaries or chiral alkenes have already been studied in depth. This study focuses on stereoselective reagent-controlled iodolactonizations, by application of a new method that uses complexes of iodine monochloride and various donor molecules. (R)-1,2,3,4-Tetrahydro-1-naphthylamine and other amines

  渗胶是许多合成序列中的重要步骤。使用手性助剂或手性烯烃的底物控制反应已得到深入研究。这项研究集中于立体选择性试剂控制的碘内酯化，方法是应用一种新方法，该方法使用一氯化碘与各种供体分子的复合物。发现（R）-1,2,3,4-四氢-1-萘胺和其他具有类似结构的胺在4-芳基-4-戊烯酸的碘环化中是有效的。对（R）-1,2,3,4-四氢-1-萘胺与XCl（X = I，H）的配合物进行了计算，以鉴定这些碘代环化反应中可能存在的反应性物种。通过使用改良的碘的SDD基集，在各种理论水平（包括B3 LYP / 6-31 + G（d，p））上进行了计算。
• Benzoyl trifluoromethanesulfonate. A mild reagent for the benzoylation of sterically hindered hydroxyls
  作者：Lindsey Brown、Masato Koreeda

  DOI：10.1021/jo00195a001

  日期：1984.10
• General synthetic method for non-K-region arene oxides
  作者：Haruhiko Yagi、Donald M. Jerina

  DOI：10.1021/ja00844a044

  日期：1975.5
• Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors
  作者：Janet Wisniewski Grissom、Detlef Klingberg、Sabine Meyenburg、Brenda L. Stallman

  DOI：10.1021/jo00104a053

  日期：1994.12

  Tandem enediyne-radical cyclizations were carried out on substrates that contain nitrile and ketone radical accepters. The products of these cyclizations and the previously reported tandem enediyne-radical cyclizations containing aldehyde and oxime ether radical accepters were compared with tributyltin hydride-mediated aryl radical addition reactions with 1-bromonaphthalene derivatives containing aldehyde, oxime ether, nitrile, and ketone radical accepters, since these substrates go through similar initial radical intermediates. Although many of the same products were observed using either method of aryl radical generation, there were distinct differences in the product composition and identity depending on which method was used. These differences can probably be primarily attributed to the temperature difference of the two modes of radical generation.