3,4-dihydro-2-hydroxy-6-methoxy-1(2H)-naphthalenone | 213249-30-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3,4-dihydro-2-hydroxy-6-methoxy-1(2H)-naphthalenone
• 英文别名: 2-hydroxy-6-methoxy-3,4-dihydronaphthalen-1(2H)-one；2-hydroxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 213249-30-0
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: XDQKYAMZGAHVMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  3,4-dihydro-2-hydroxy-6-methoxy-1(2H)-naphthalenone 在 potassium fluoride 、 2-氟吡啶 、 四甲基乙二胺 、 sodium hexamethyldisilazane 、 Selectfluor 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 13.0h， 生成 allyl (6-methoxy-2-(trifluoromethoxy)-3,4-dihydronaphthalen-1-yl) carbonate
  参考文献：
  名称：

  通过钯催化烯丙基碳酸烯丙酯的脱羧烯丙基烷基化 反应，不对称合成具有四取代α-立体异构中心的α-三氟甲氧基酮†

  摘要：

  钯催化的三氟甲氧基烯丙基烯醇碳酸酯的不对称脱羧烯丙基烷基化反应可得到富含对映体的α-三氟甲氧基烯丙基酮，其特征在于四取代的α-立体异构中心，具有优异的收率和高对映选择性。该方法进一步扩展到α-二氟甲氧基和α-甲氧基烯丙基酮的不对称合成，该合成在相似的催化条件下进行。

  DOI：

  10.1039/c8cc03131b
• 作为产物：
  描述：

  6-甲氧基-1-萘满酮 在 potassium hydroxide 、 盐酸 作用下， 以 甲醇 、 四氢呋喃 、 水 为溶剂， 反应 2.25h， 以55%的产率得到3,4-dihydro-2-hydroxy-6-methoxy-1(2H)-naphthalenone
  参考文献：
  名称：

  通过钯催化烯丙基碳酸烯丙酯的脱羧烯丙基烷基化 反应，不对称合成具有四取代α-立体异构中心的α-三氟甲氧基酮†

  摘要：

  钯催化的三氟甲氧基烯丙基烯醇碳酸酯的不对称脱羧烯丙基烷基化反应可得到富含对映体的α-三氟甲氧基烯丙基酮，其特征在于四取代的α-立体异构中心，具有优异的收率和高对映选择性。该方法进一步扩展到α-二氟甲氧基和α-甲氧基烯丙基酮的不对称合成，该合成在相似的催化条件下进行。

  DOI：

  10.1039/c8cc03131b

文献信息

• Intramolecular [3 + 2]cycloadditions: synthesis of 1-methylene-2,3,3a,4,5,9b-hexahydro-1H-benz[e]indenes and an unsuccessful approach to ergot alkaloids
  作者：Michael P. Collins、Michael G. B. Drew、John Mann、Harry Finch

  DOI：10.1039/p19920003211

  日期：——

  3-enyl)-4-methoxybenzenes, prepared by a short synthesis, underwent intramolecular [3 + 2]cycloadditions to produce the title indenes. An analogous intramolecular cycloaddition was attempted with N-benzyl-4-(2-methoxyvinyl)-3-(2-hydroxy-3-trimethylsilylmethylbut-3-enyl)indoline, in an attempt to produce a key intermediate for ergot alkaloid synthesis, but this was unsuccessful.

  通过短合成法制备的1-（1-羟基-2-三甲基甲硅烷基甲基丙-2-烯基）-2-（4-取代的丁-3-烯基）-4-甲氧基苯经历分子内[3 + 2]环加成反应头衔。尝试用N-苄基-4-（2-甲氧基乙烯基）-3-（2-羟基-3-三甲基甲硅烷基甲基丁-3-烯基）二氢吲哚进行类似的分子内环加成反应，以尝试生成麦角生物碱合成的关键中间体，但是这是不成功的。
• Synthesis of chiral acetoxy lactones via the Baeyer–Villiger oxidation of cyclic aromatic acetoxy ketones
  作者：Ayhan S. Demir、Asuman Aybey

  DOI：10.1016/j.tet.2008.09.035

  日期：2008.12

  kinetic resolution of acetoxy ketones furnished both of the enantiomers of α-acetoxy ketones in good chemical and optical yields. The Baeyer–Villiger oxidation of α-acetoxy ketones with m-CPBA, CF3SO3H, and CH2Cl2, at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords phenolic α-hydroxycarboxylic

  通过使用Mn（OAc）3进行茚满酮和四氢萘酮的α-乙酰氧基化反应，然后酶催化乙酰氧基酮的动力学拆分，以良好的化学和光学收率提供了α-乙酰氧基酮的两种对映体。在室温下，使用m -CPBA，CF 3 SO 3 H和CH 2 Cl 2进行α-乙酰氧基酮的Baeyer-Villiger氧化，得到相应的内酯，而没有消旋化。乙酰氧基酮部分选择性迁移以形成内酯。内酯的温和水解得到酚类α-羟基羧酸衍生物。
• Allylindation of 6-Substituted 2-Hydroxy-1-tetralones in Aqueous and Organic Media. Stereochemistry and Competition Studies
  作者：Paul C. Lobben、Leo A. Paquette

  DOI：10.1021/jo980825f

  日期：1998.10.1

  A systematic investigation of the stereoselectivity associated with coupling reactions involving the allylindium reagent-and 6-substituted 2-hydroxy-1-tetralones is presented. In each instance, the allylations were carried out in water, 50% aqueous THF, and dry THF. The extent of 1,2-induction was found to be highest-in THF-H2O (1:1) and to favor the trans diol isomer. Somewhat lower levels of stereochemical bias in the same direction were observed in pure water. However, further erosion of this trend was noted for those reactions performed in THF, such that a modest crossover in product distribution became apparent in certain examples. On the basis of competition experiments, both reaction trajectories give evidence of proceeding via chelated intermediates. The extent of stereoinduction was found to be in Line with the normal predilection of 2-cyclohexenones for axial attack, which is the process believed to be beset with minimal torsional effects. The substituents situated para to the ketone carbonyl do not exert a very large influence on product distribution, although electronic effects are evident in the context of the competition studies. A mechanistic model which integrates these findings is offered.
• Asymmetric synthesis of α-trifluoromethoxy ketones with a tetrasubstituted α-stereogenic centre <i>via</i> the palladium-catalyzed decarboxylative allylic alkylation of allyl enol carbonates
  作者：Hiroya Kondo、Mayaka Maeno、Kazuki Hirano、Norio Shibata

  DOI：10.1039/c8cc03131b

  日期：——

  The palladium-catalyzed asymmetric decarboxylative allylic alkylation of trifluoromethoxy allyl enol carbonates afforded enantioenriched α-trifluoromethoxy allyl ketones that feature a tetrasubstituted α-stereogenic center in excellent yield and high enantioselectivity. The method was further extended to the asymmetric synthesis of α-difluoromethoxy and α-methoxy allyl ketones, which proceeded under

  钯催化的三氟甲氧基烯丙基烯醇碳酸酯的不对称脱羧烯丙基烷基化反应可得到富含对映体的α-三氟甲氧基烯丙基酮，其特征在于四取代的α-立体异构中心，具有优异的收率和高对映选择性。该方法进一步扩展到α-二氟甲氧基和α-甲氧基烯丙基酮的不对称合成，该合成在相似的催化条件下进行。