2-methyl-4-phenyl-1H-benzisoindole-1,3(2H)-dione | 60231-30-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 2-methyl-4-phenyl-1H-benzisoindole-1,3(2H)-dione
• 英文别名: 1-Phenyl-2,3-naphthalindicarbonsaeure-N-methyl-imid；N-Methyl-1-phenyl-naphthalendicarboximide-2,3；2-methyl-4-phenylbenzo[f]isoindole-1,3-dione
• CAS: 60231-30-3
• 化学式: C₁₉H₁₃NO₂
• 分子量: 287.318
• InChiKey: OXFQERCQYWQBTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻苯甲酰苯甲酸 在 氢氧化钾 、 sodium tetrahydroborate 、 甲烷磺酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 21.0h， 生成 2-methyl-4-phenyl-1H-benzisoindole-1,3(2H)-dione
  参考文献：
  名称：

  Stereochemistry of lithium dialkylamide-induced 1,4-eliminations leading to substituted isobenzofurans

  摘要：

  DOI：

  10.1021/jo00370a019

文献信息

• Facile Sc(OTf)₃-Catalyzed Generation and Successive Aromatization of Isobenzofuran from <i>o</i>-Dicarbonylbenzenes
  作者：Yuta Nishina、Tatsuya Kida、Tomonari Ureshino

  DOI：10.1021/ol201479p

  日期：2011.8.5

  Isobenzofuran can be prepared from o-phthalaldehyde using hydrosilane. The formed isobenzofuran is trapped by an alkene via a Diels–Alder reaction. Further dehydration proceeds to furnish the conjugated aromatic compound. This multistep reaction was promoted by catalytic amounts of Sc(OTf)3.

  异苯并呋喃可以使用氢化硅烷由邻苯二甲醛制备。形成的异苯并呋喃通过狄尔斯-阿尔德反应被烯烃捕获。进一步脱水以提供共轭芳族化合物。催化量的Sc（OTf）3促进了该多步反应。
• Rhenium-Catalyzed Synthesis of Indenones by Novel Dehydrative Trimerization of Aryl Aldehydes via C−H Bond Activation
  作者：Yoichiro Kuninobu、Takashi Matsuki、Kazuhiko Takai

  DOI：10.1021/ol100947p

  日期：2010.7.2

  By heating aryl aldehydes with catalytic amounts of a rhenium complex, ReBr(CO)(5), and N-phenylacetamide in toluene, indenone derivatives are obtained in good to excellent yields. This reaction proceeds via (1) the formation of an isobenzofuran derivative by the insertion of an aldehyde into the C-H bond of another aldehyde (C-H bond activation) and successive intramolecular nucleophilic cyclization, (2) nucleophilic addition of the formed isobenzofuran derivative to the third aldehyde, (3) isomerization, and (4) intramolecular aldol condensation.
• RIGAUDY J.; PERLAT M.-C.; SIMON D.; KIM CUONG NGUYEN, BULL. SOC. CHIM. FRANCE <BSCF-AS>, 1976, NO 3-4, PART. 2, 493-500
  作者：RIGAUDY J.、 PERLAT M.-C.、 SIMON D.、 KIM CUONG NGUYEN

  DOI：——

  日期：——
• Stereochemistry of lithium dialkylamide-induced 1,4-eliminations leading to substituted isobenzofurans
  作者：David Tobia、Bruce Rickborn

  DOI：10.1021/jo00370a019

  日期：1986.10