4a-methoxy-5,6,7,8-tetrahydronaphthalen-2(4aH)-one | 23438-28-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4a-methoxy-5,6,7,8-tetrahydronaphthalen-2(4aH)-one
• 英文别名: 5,6,7,8-Tetrahydro-4a-methoxynaphthalen-2(4aH)-one；4-methoxy-5,6,7,8-tetrahydronaphthalen-2-one；Tetralin-p-chinol-methylether；4a-Methoxy-5,6,7,8-tetrahydronaphthalen-2-one
• CAS: 23438-28-0
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: QHTDZBGLYJQLAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4a-methoxy-5,6,7,8-tetrahydronaphthalen-2(4aH)-one 在 甲酸 、 sodium dithionite 、 四丁基溴化铵 、 potassium carbonate 、 钯 、 potassium hydroxide 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 28.5h， 生成 6-hydroxy-7,12-dimethoxy-3,4-dihydrotetraphen-1(2H)-one
  参考文献：
  名称：

  Selective Oxidative Dearomatization of Angular Tetracyclic Phenols by Controlled Irradiation under Air: Synthesis of an Angucyclinone-Type Double Peroxide with Anticancer Properties

  摘要：

  Angular tetracyclic p-peroxyquinols, p-quinols, and a pentacyclic double peroxide, showing anticancer properties, were synthesized from the corresponding phenols by an environmentally friendly solvent- and wavelength-controlled irradiation under air in the absence of an external photosensitizer.

  DOI：

  10.1021/acs.orglett.8b02515
• 作为产物：
  描述：

  4'a-Methoxy-5,5-dimethyl-5',6',7',8'-tetrahydro-4'aH-spiro[[1,3]dioxolane-2,2'-naphthalen]-4-one 在 氢氧化钾 作用下， 生成 4a-methoxy-5,6,7,8-tetrahydronaphthalen-2(4aH)-one
  参考文献：
  名称：

  Directed conversion of the phenoxy grouping into a variety of cyclic polyfunctional systems

  摘要：

  DOI：

  10.1021/ja01045a034

文献信息

• Regioselective and Chemoselective Reduction of Naphthols Using Hydrosilane in Methanol: Synthesis of the 5,6,7,8-Tetrahydronaphthol Core
  作者：Yuan He、Jinghua Tang、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/acs.orglett.8b01273

  日期：2018.7.20

  A regioselective and chemoselective method for catalytic synthesis of biologically interesting 5,6,7,8-tetrahydronaphthols by reduction of naphthols was described. The side aromatic hydrocarbons in naphthols were site-selectively reduced, using hydrosilanes in methanol, allowing for retaining functional phenol scaffolds intact. It presents a rare example of using low-cost and air-stable hydrosilane

  描述了一种区域选择性和化学选择性方法，用于通过还原萘酚催化合成生物学上令人感兴趣的5,6,7,8-四氢萘酚。使用甲醇中的氢硅烷可选择性地还原萘酚中的侧链芳香烃，从而使功能性酚骨架保持完整。它提供了一个罕见的示例，该示例使用低成本且空气稳定的氢化硅烷在温和条件下催化还原未活化的芳烃。该反应是可扩展的，并且以高选择性进行，而没有形成1,2,3,4-四氢萘酚副产物，其可耐受敏感的官能团，例如溴化物，氯化物，氟化物，酮，酯和酰胺。
• Anionic [4+2] cycloaddition strategy in the regiospecific synthesis of carbazoles: formal synthesis of ellipticine and murrayaquinone A
  作者：Dipakranjan Mal、Bidyut Kumar Senapati、Pallab Pahari

  DOI：10.1016/j.tet.2007.02.060

  日期：2007.4

  Anionic [4+2] cycloaddition of furoindolones (e.g., 7 and 10) has been developed as an effective means to the synthesis of carbazoles. This reaction has been shown to be feasible with a wide variety of Michael acceptors to give carbazoles and fused carbazoles in good yields. The scope and limitations of the reaction have been briefly studied. The nature of N-protection of the furoindolones (cf. 7)

  呋喃吲哚酮（例如7和10）的阴离子[4 + 2]环加成已被开发为咔唑合成的有效手段。已经表明该反应对于多种迈克尔受体是可行的，以高收率得到咔唑和稠合咔唑。已经简要研究了反应的范围和局限性。呋喃吲哚酮的N-保护性质（参见7）在环切成功中起着重要作用。
• A Variation of the Fischer Indolization Involving Condensation of Quinone Monoketals and Aliphatic Hydrazines
  作者：Jinzhu Zhang、Zhiwei Yin、Patrick Leonard、Jing Wu、Kate Sioson、Che Liu、Robert Lapo、Shengping Zheng

  DOI：10.1002/anie.201207533

  日期：2013.2.4

  new twist: A one‐pot nitrous acid free, diazonium‐free, and transition‐metal‐free variation of the Fischer indole synthesis has been developed. Condensation of quinone monoketals and aliphatic hydrazine hydrochlorides afforded indoles via intermediate alkylaryldiazenes. This method will complement the classical Fischer indole synthesis by providing indoles in two steps from widely available phenols

  一个新的转折：已开发出Fischer吲哚合成的一锅无亚硝酸，无重氮和无过渡金属的变体。醌单缩酮和脂族肼盐酸盐的缩合通过中间体烷基芳基二氮烯得​​到吲哚。该方法将在温和的条件下从两步制得的苯酚中分两步提供吲哚，从而补充了经典的Fischer吲哚合成方法。
• Total synthesis of BE-23254, a chlorinated angucycline antibiotic
  作者：Satyajit Dey、Dipakranjan Mal

  DOI：10.1016/j.tetlet.2005.06.062

  日期：2005.8

  The first synthesis of BE-23254, an unusual angucycline antibiotic, is reported. It involves regioselective condensation of naphthalenone 4 and chlorine-containing isobenzofuranone 16 as the key step.

  据报道，BE-23254是一种罕见的安古环素抗生素的首次合成。这是关键步骤，包括萘酮4和含氯异苯并呋喃酮16的区域选择性缩合。
• 4-Fluorocyclohexa-2,5-dienones as new acceptors for the Hauser annulation
  作者：Pallab Pahari、Bidyut Senapati、Dipakranjan Mal

  DOI：10.1016/j.tetlet.2007.01.159

  日期：2007.4

  4-Fluorocyclohexa-2,5-dienones are introduced as new acceptors for the Hauser annulation. In cases where the corresponding methoxy analogs fail to undergo annulation, the former smoothly do so with phenylsulfonyl phthalides to furnish anthraquinones in good yields. Steric effects are implicated to explain the inertness of the methoxy analogs.

  引入4-氟环己基2,5-二壬烯作为豪瑟环化反应的新受体。在相应的甲氧基类似物不能进行环合的情况下，前者可以与苯磺酰邻苯二甲酸酯一起顺畅地进行，从而以高收率提供蒽醌。涉及立体效应来解释甲氧基类似物的惰性。