methyl 2-methyl-1-indanone-2-acetate | 651715-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: methyl 2-methyl-1-indanone-2-acetate
• 英文别名: methyl 2-(2,3-dihydro-2-methyl-1-oxo-1H-inden-2-yl)acetate；1H-Indene-2-acetic acid, 2,3-dihydro-2-methyl-1-oxo-, methyl ester；methyl 2-(2-methyl-3-oxo-1H-inden-2-yl)acetate
• CAS: 651715-63-8
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: LUIGLZKCHWYLSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-methyl-1-indanone-2-acetate 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以59%的产率得到2-hydroxy-2,3-methano-3-methyl-1-oxo-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Novel transformation of 2-substituted alkyl 1-indanone-2-acetates to 6-substituted 3,4-benzotropolones through sequential reduction and oxidation processes using Sm(II) and Ce(IV) salts

  摘要：

  When 2-substituted alkyl 1-indanone-2-acetates 1 were treated with samarium diiodide, 3-substituted 2-hydroxy-2,3-methano-1-oxo-1,2,3,4-tetrahydronaphthalenes 4 were obtained. The reaction is proposed to proceed through a rearrangement initiated by intramolecular ketone-ester coupling. Oxidation of these products 4 or their silyl ethers 13 by ceric(IV) ammonium nitrate involving regioselective bond cleavage of their bicyclo[4.1.0]-rings produced the corresponding benzotropolone derivatives 10. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.083
• 作为产物：
  描述：

  乙基1-氧亚基-2,3-二氢-1H-茚-2-甲酸基酯 在 氢溴酸 、 sodium hydride 作用下， 生成 methyl 2-methyl-1-indanone-2-acetate
  参考文献：
  名称：

  Novel transformation of 2-substituted alkyl 1-indanone-2-acetates to 6-substituted 3,4-benzotropolones through sequential reduction and oxidation processes using Sm(II) and Ce(IV) salts

  摘要：

  When 2-substituted alkyl 1-indanone-2-acetates 1 were treated with samarium diiodide, 3-substituted 2-hydroxy-2,3-methano-1-oxo-1,2,3,4-tetrahydronaphthalenes 4 were obtained. The reaction is proposed to proceed through a rearrangement initiated by intramolecular ketone-ester coupling. Oxidation of these products 4 or their silyl ethers 13 by ceric(IV) ammonium nitrate involving regioselective bond cleavage of their bicyclo[4.1.0]-rings produced the corresponding benzotropolone derivatives 10. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.083

文献信息

• Intramolecular Palladium-Catalyzed Alkane C−H Arylation from Aryl Chlorides
  作者：Sophie Rousseaux、Michaël Davi、Julien Sofack-Kreutzer、Cathleen Pierre、Christos E. Kefalidis、Eric Clot、Keith Fagnou、Olivier Baudoin

  DOI：10.1021/ja1048847

  日期：2010.8.11

  efficient and general palladium-catalyzed intramolecular C(sp(3))-H arylation of (hetero)aryl chlorides, giving rise to a variety of valuable cyclobutarenes, indanes, indolines, dihydrobenzofurans, and indanones, are described. The use of aryl and heteroaryl chlorides significantly improves the scope of C(sp(3))-H arylation by facilitating the preparation of reaction substrates. Careful optimization studies

  描述了有效和通用的钯催化分子内 C(sp(3))-H 芳基化（杂）芳基氯化物的第一个例子，产生了各种有价值的环丁烷、茚满、二氢吲哚、二氢苯并呋喃和茚满酮。芳基和杂芳基氯化物的使用通过促进反应底物的制备显着改善了 C(sp(3))-H 芳基化的范围。仔细的优化研究表明，钯配体和碱/溶剂组合对于以高产率获得所需类别的产品至关重要。总体而言，采用 P(t)Bu(3)、PCyp(3) 或 PCy(3) 作为钯配体和 K(2)CO(3)/DMF 或 Cs(2)CO(3) 的三组反应条件)/新戊酸/均三甲苯作为碱/溶剂组合允许使用此方法访问五种不同类别的产品。总共，已成功进行了 40 多个 CH 芳基化实例。当底物中存在几种类型的 C(sp(3))-H 键时，发现芳基化在初级 CH 键与二级或三级位置发生区域选择性。此外，在存在几个主要 CH 键的情况下，选择性趋势与钯环中间体的大小相关，五元环比六元
• Novel transformation of 2-substituted alkyl 1-indanone-2-acetates to 6-substituted 3,4-benzotropolones through sequential reduction and oxidation processes using Sm(II) and Ce(IV) salts
  作者：Kazuki Iwaya、Mutsuko Tamura、Momoe Nakamura、Eietsu Hasegawa

  DOI：10.1016/j.tetlet.2003.10.083

  日期：2003.12

  When 2-substituted alkyl 1-indanone-2-acetates 1 were treated with samarium diiodide, 3-substituted 2-hydroxy-2,3-methano-1-oxo-1,2,3,4-tetrahydronaphthalenes 4 were obtained. The reaction is proposed to proceed through a rearrangement initiated by intramolecular ketone-ester coupling. Oxidation of these products 4 or their silyl ethers 13 by ceric(IV) ammonium nitrate involving regioselective bond cleavage of their bicyclo[4.1.0]-rings produced the corresponding benzotropolone derivatives 10. (C) 2003 Elsevier Ltd. All rights reserved.