7a-Methoxy-1,2,3,7a-tetrahydro-inden-5-one | 55153-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7a-Methoxy-1,2,3,7a-tetrahydro-inden-5-one
• 英文别名: 7a-methoxy-2,3-dihydro-1H-inden-5-one
• CAS: 55153-56-5
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: ZQVTTXBDZWIZOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  ethyl 1,3-dihydro-3-oxo-1-(phenylsulfonyl)-4H-furo[3,4-b]indole-4-carboxylate 、 7a-Methoxy-1,2,3,7a-tetrahydro-inden-5-one 在 lithium tert-butoxide 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 以75%的产率得到5-hydroxy-1,2,3,7-tetrahydroindeno[6,7-b]carbazole-6,12-dione
  参考文献：
  名称：

  咔唑的区域特异性合成中的阴离子[4 + 2]环加成策略：玫瑰树碱和Murrayaquinone A的正式合成

  摘要：

  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。

  DOI：

  10.1016/j.tet.2007.02.060
• 作为产物：
  描述：

  甲醇 、 5-茚醇 在 碘苯二乙酸 作用下， 反应 1.0h， 以89%的产率得到7a-Methoxy-1,2,3,7a-tetrahydro-inden-5-one
  参考文献：
  名称：

  BAIB Oxidation to Some Tetrahydro‐β‐naphthols and Control over the Products by Reaction Condition Selection

  摘要：

  Using two different conditions for the BAIB [bis(acetoxyiodo)benzene] oxidation to tetrahydro-beta-naphthols or substituted tetrahydro-beta-naphthols furnished two different products with excellent yields.

  DOI：

  10.1080/00397910500182556

文献信息

• Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)‐ABX
  作者：Jing‐Kai Huang、Kak‐Shan Shia

  DOI：10.1002/anie.201914657

  日期：2020.4.16

  vinylogous [4+2] anionic annulation has been newly developed, the cascade process of which has a high preference for regiochemical control and chemoselectivity, giving rise to exclusively Michael-type adducts in moderate to high yields (up to 94 %, 35 examples). By making use of this approach as a key operation, the first total synthesis of natural antibiotic ABX, in racemic form, has been successfully

  交叉共轭的乙烯基[4 + 2]阴离子环化技术已经得到了新的发展，其级联工艺对区域化学控制和化学选择性具有很高的偏爱，从而以中等至高的收率（高达94％的产率）产生了唯一的迈克尔型加合物。 （35个示例）。通过将该方法用作关键操作，已成功地以简明的7个步骤成功完成了外消旋形式的天然抗生素ABX的首次全合成，总收率约为20％。
• 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。
• A room temperature alternative of the Claisen rearrangement route to ortho allylated phenols: unique reactivity pattern of allylindium reagents
  作者：Dipakranjan Mal、Pallab Pahari、Bidyut K. Senapati

  DOI：10.1016/j.tetlet.2005.01.152

  日期：2005.3

  Quinol ethers and quinone monoketals are shown to undergo formal anti-Michael addition reactions with allylindium reagents at room temperature to give only ortho allylated phenols in good yields.

  已显示喹醇醚和醌单缩酮在室温下与烯丙基化试剂进行正式的抗迈克尔加成反应，从而以高收率仅得到邻位烯丙基化的苯酚。
• A rapid access to hydroxylated benz[a]anthraquinones: Hypervalent iodine oxidation of β-naphthols
  作者：Dipakranjan Mal、Harendra N. Roy、Nirmal K. Hazra、Susanta Adhikari

  DOI：10.1016/s0040-4020(96)01119-2

  日期：1997.2

  Anionic annulation of phthalide sulfones 3 with quinone monoketals 6, accessible by phenyliodonium diacetate oxidation of naphthols 5, offers a high yielding regiospecific entry to benz[a]anthraquinones 8. Similar annulation of cyanophthalide 13 with 12, followed by photooxygenation of 14 results in a complementary route to the basic skeleton 15 of nonaromatic A-ring angucyclines. (C) 1997, Published by Elsevier Science Ltd.
• 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。