6-chloro-3-methyl-3,4-dihydroisocoumarin | 72989-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-chloro-3-methyl-3,4-dihydroisocoumarin
• 英文别名: 6-chloro-3-methylisochroman-1-one；6-Chloro-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one；6-chloro-3-methyl-3,4-dihydroisochromen-1-one
• CAS: 72989-49-2
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: BFCWQEMDQPMTFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  6-chloro-3-methyl-3,4-dihydroisocoumarin 以75%的产率得到
  参考文献：
  名称：

  BHIDE B. H.; GUPTA V. P., INDIAN J. CHEM., 1979, B 17, NO 3, 295

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苯 N-苯甲酰苯胺 在 正丁基锂 、 硫酸 作用下， 反应 8.5h， 生成 6-chloro-3-methyl-3,4-dihydroisocoumarin
  参考文献：
  名称：

  Application of organolithium and related reagents in synthesis, Part X. Metallation-electrophilic substitution sequence of secondary chlorobenzamides

  摘要：

  The lithiation (Bu(n)Li/THF) of 2-chloro- (1), 3-chloro- (2) and 4-chlorobenzanilides (3) and the subsequent reactions of the corresponding bis-lithiated anilides 4 - 6 with electrophiles (MeI, CH2 = CH - CH2Br, Me3SiCl, MeCHO, o-MeOC6H4CHO, p-MeOC6H4CHO, Me2NCHO and p-MeOC6H4CONMe2) towards the synthesis of the ortho substituted chlorobenzoesic acids derivatives 12 - 14 have been described. The effect of the chlorine substituent upon the generation and stability of the bis-lithiated chloro-anilides 4 - 6 has been studied. It has been found that the bis-lithiated chloro-anilide 5 derived from m-chloro-benzanilide (2) at a temperature above - 30-degrees-C converts into the corresponding benzyne 9. The anilide moiety (masking group) of the formed ortho-substituted chlorobenzanilides appeared to be effectively removable on acid-driven hydrolysis.

  DOI：

  10.1007/bf00808275

文献信息

• Temperature-controlled redox-neutral ruthenium(<scp>ii</scp>)-catalyzed regioselective allylation of benzamides with allylic acetates
  作者：Rajendran Manikandan、Masilamani Jeganmohan

  DOI：10.1039/c6ob01498d

  日期：——

  Substituted aromatic amides reacted efficiently with allylic acetates in the presence of a cationic ruthenium complex in ClCH2CH2Cl at room temperature providing ortho allylated benzamides in a highly regioselective manner without any oxidant and base. The whole catalytic reaction occurred in a Ru(II) oxidation state and thus the oxidation step is avoided. By tuning the reaction temperature, ortho allyl

  取代的芳族酰胺在阳离子钌络合物存在下于室温在ClCH 2 CH 2 Cl中与乙酸烯丙酯有效反应，以高度区域选择性的方式提供邻位烯丙基化的苯甲酰胺，而无需任何氧化剂和碱。整个催化反应以Ru（II）氧化态发生，因此避免了氧化步骤。通过调节反应温度，仅制备邻烯丙基和乙烯基苯甲酰胺。后来，在盐酸存在下，将邻烯丙基和乙烯基化的苯甲酰胺转化为生物学上有用的六元和五元苯并内酯。
• KORTE D. E.; HEGEDUS L. S.; WIRTH R. K., J. ORG. CHEM. <JOCE-AH>, 1977, 42, NO 8, 1329-1336
  作者：KORTE D. E.、 HEGEDUS L. S.、 WIRTH R. K.

  DOI：——

  日期：——
• Application of organolithium and related reagents in synthesis, Part X. Metallation-electrophilic substitution sequence of secondary chlorobenzamides
  作者：Jan Epsztajn、Adam Bieniek、Justyna A. Kowalska、Jacek Ścianowski

  DOI：10.1007/bf00808275

  日期：1992.12

  The lithiation (Bu(n)Li/THF) of 2-chloro- (1), 3-chloro- (2) and 4-chlorobenzanilides (3) and the subsequent reactions of the corresponding bis-lithiated anilides 4 - 6 with electrophiles (MeI, CH2 = CH - CH2Br, Me3SiCl, MeCHO, o-MeOC6H4CHO, p-MeOC6H4CHO, Me2NCHO and p-MeOC6H4CONMe2) towards the synthesis of the ortho substituted chlorobenzoesic acids derivatives 12 - 14 have been described. The effect of the chlorine substituent upon the generation and stability of the bis-lithiated chloro-anilides 4 - 6 has been studied. It has been found that the bis-lithiated chloro-anilide 5 derived from m-chloro-benzanilide (2) at a temperature above - 30-degrees-C converts into the corresponding benzyne 9. The anilide moiety (masking group) of the formed ortho-substituted chlorobenzanilides appeared to be effectively removable on acid-driven hydrolysis.
• BHIDE B. H.; GUPTA V. P., INDIAN J. CHEM., 1979, B 17, NO 3, 295
  作者：BHIDE B. H.、 GUPTA V. P.

  DOI：——

  日期：——