(Z)-3-allylidene-2,3-dihydro-1H-isoindolin-1-one | 132855-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (Z)-3-allylidene-2,3-dihydro-1H-isoindolin-1-one
• 英文别名: 3-[(Z)-2-propenylidene]-1-isoindolinone；3-(2-propenylidene)phthalimidine；(3Z)-3-prop-2-enylideneisoindol-1-one
• CAS: 132855-11-9
• 化学式: C₁₁H₉NO
• 分子量: 171.199
• InChiKey: SHYJWSFHSOAUHO-YHYXMXQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-allyl-3-hydroxyphthalimidine 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以67%的产率得到(Z)-3-allylidene-2,3-dihydro-1H-isoindolin-1-one
  参考文献：
  名称：

  Preparation and some reactions of allylic indium reagents

  摘要：

  A variety of allylic indium sesquihalides were readily prepared by the reaction of indium powder with allylic halides in DMF at room temperature. Protonation of the allylindium reagents proceeded regiospecifically at the gamma-position of the allylic group to give 1-propenes. A facile transformation of alpha-pinene to beta-pinene was achieved via a myrtenylindium intermediate. Oxygenation of the allylic indium reagents gave mixtures of allylic alcohol isomers in moderate yields. The coupling of the allylindium reagents with cyclic imides gave diverse products depending on the structures of the substrates and the reagents. Stannylation with tributylchlorostanane occurred exclusively at the alpha-carbon, yielding allytributylstannanes; E, Z isomerization of the allylic double bond depended largely upon the substitution pattern on the allylic moiety.

  DOI：

  10.1021/jo00007a050

文献信息

• Direct construction of a quaternary carbon center utilizing an organosamarium reagent
  作者：Zhifang Li、Yongmin Zhang

  DOI：10.1016/s0040-4039(01)01831-7

  日期：2001.11

  Direct geminal diallylation of lactams and acyclic amides containing an NH bond has been achieved in the presence of allylsamarium bromide. By applying this method, quaternary carbons have been constructed, and 2,2-diallylated nitrogen heterocycles and diallylated amides were synthesized in moderate to good yields under mild conditions.

  在烯丙基溴化mar的存在下，内酰胺和含有NH键的无环酰胺的直接双键二烯丙基化反应已经实现。通过应用该方法，已经构建了季碳，并且在温和的条件下以中等至良好的收率合成了2，2-二烯丙基化的氮杂环和二烯丙基化的酰胺。
• Direct construction of quaternary carbon center utilizing an allylsamarium bromide reagent
  作者：Zhifang Li、Yongmin Zhang

  DOI：10.1016/s0040-4020(02)00491-x

  日期：2002.6

  Direct geminal diallylation of lactones, lactams and acyclic amides containing a N–H bond has been achieved in the presence of allylsamarium bromide. By applying this method, quaternary carbons have been constructed, and 2,2-diallylated cyclic ethers, 2,2-diallylated nitrogen heterocycles and diallylated amides were synthesized in moderate to good yields under mild conditions.

  在烯丙基溴化presence的存在下，内酯，内酰胺和含有N–H键的无环酰胺的直接双键二烯丙基化反应已经实现。通过应用该方法，已经构建了季碳，并且在温和的条件下以中等至良好的收率合成了2,2-二烯丙基化的环醚，2,2-二烯丙基化的氮杂环和二烯丙基化的酰胺。
• A Tandem Elimination−Cyclization−Suzuki Approach: Efficient One-Pot Synthesis of Functionalized (<i>Z</i>)-3-(Arylmethylene)isoindolin-1-ones
  作者：Caiyun Sun、Bin Xu

  DOI：10.1021/jo801219j

  日期：2008.9.19

  A novel and efficient one-pot regioselective elimination-cyclization-Suzuki approach was developed to afford (Z)-3-arylmethyleneisoindolin-1-ones in good to excellent yields from easily accessible o-gem-dihalovinylbenzamides and organoboron reagents.
• ARAKI, SHUKI;SHIMISU, TOSHIO;JOHAR, PERMINDER S.;JIN, SHUN-JI;BUTSUGAN, Y+, J. ORG. CHEM., 56,(1991) N, C. 2538-2542
  作者：ARAKI, SHUKI、SHIMISU, TOSHIO、JOHAR, PERMINDER S.、JIN, SHUN-JI、BUTSUGAN, Y+

  DOI：——

  日期：——
• Preparation and some reactions of allylic indium reagents
  作者：Shuki Araki、Toshio Shimizu、Perminder S. Johar、Shun Ji Jin、Yasuo Butsugan

  DOI：10.1021/jo00007a050

  日期：1991.3

  A variety of allylic indium sesquihalides were readily prepared by the reaction of indium powder with allylic halides in DMF at room temperature. Protonation of the allylindium reagents proceeded regiospecifically at the gamma-position of the allylic group to give 1-propenes. A facile transformation of alpha-pinene to beta-pinene was achieved via a myrtenylindium intermediate. Oxygenation of the allylic indium reagents gave mixtures of allylic alcohol isomers in moderate yields. The coupling of the allylindium reagents with cyclic imides gave diverse products depending on the structures of the substrates and the reagents. Stannylation with tributylchlorostanane occurred exclusively at the alpha-carbon, yielding allytributylstannanes; E, Z isomerization of the allylic double bond depended largely upon the substitution pattern on the allylic moiety.