2-甲基二氢吲哚-3-酮肟 | 102735-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 2-甲基二氢吲哚-3-酮肟
• 英文名称: 1,2-Dihydro-2-methyl-3H-indol-3-one oxime
• 英文别名: N-(2-methyl-1,2-dihydroindol-3-ylidene)hydroxylamine
• CAS: 102735-86-4
• 化学式: C₉H₁₀N₂O
• 分子量: 162.191
• InChiKey: MXBWJSWZSGYLPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diphenyliodonium triflate 、 2-甲基二氢吲哚-3-酮肟 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以67%的产率得到2-methylindolin-3-one O-phenyl oxime
  参考文献：
  名称：

  Synthesis of N-Aryl Oxindole Nitrones through a Metal-Free Selective N-Arylation Process

  摘要：

  An efficient selective N-arylation of 3-(hydroxyimino)indolin-2-ones with diaryliodonium salts to prepare (Z)-N-aryl oxindole nitrones has been achieved under simple base-mediated conditions. The reaction tolerated a variety of diaryliodonium salts with diverse and sensitive functional groups. Studies on the oxime structures revealed that the pyrroline ring and carbonyl group in 3-(hydroxyimino)indolin-2-ones played important roles in the selective N-arylation process. The N-aryl oxindole nitrones could be prepared rapidly and easily at the gram scale.

  DOI：

  10.1021/acs.joc.6b02774
• 作为产物：
  描述：

  2-methyl-1,2-dihydro-3H-indol-3-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 为溶剂， 反应 1.0h， 生成 2-甲基二氢吲哚-3-酮肟
  参考文献：
  名称：

  Synthesis of N-Aryl Oxindole Nitrones through a Metal-Free Selective N-Arylation Process

  摘要：

  An efficient selective N-arylation of 3-(hydroxyimino)indolin-2-ones with diaryliodonium salts to prepare (Z)-N-aryl oxindole nitrones has been achieved under simple base-mediated conditions. The reaction tolerated a variety of diaryliodonium salts with diverse and sensitive functional groups. Studies on the oxime structures revealed that the pyrroline ring and carbonyl group in 3-(hydroxyimino)indolin-2-ones played important roles in the selective N-arylation process. The N-aryl oxindole nitrones could be prepared rapidly and easily at the gram scale.

  DOI：

  10.1021/acs.joc.6b02774

文献信息

• Copper-Catalyzed Selective <i>N</i>-Vinylation of 3-(Hydroxyimino)indolin-2-ones with Alkenyl Boronic Acids: Synthesis of <i>N</i>-Vinyl Nitrones and Spirooxindoles
  作者：Chun-Hua Chen、Qing-Qing Liu、Xiao-Pan Ma、Yu Feng、Cui Liang、Cheng-Xue Pan、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1021/acs.joc.7b00620

  日期：2017.6.16

  A copper-catalyzed selective cross-coupling reaction of 3-(hydroxyimino)indolin-2-ones with alkenyl boronic acids to access (E)-N-vinyl oxindole nitrones has been achieved under mild conditions. The studies showed that catalytic copper salt selectively gave mono N-vinylation products, while 2.0 equiv of copper salt provided double N-vinylation products. The control experiments revealed that the carbonyl

  在温和的条件下，铜催化了3-（羟基亚氨基）吲哚啉-2-酮与烯基硼酸的选择性交联反应，以使其进入（E）-N-乙烯基氧吲哚腈。研究表明，催化铜盐选择性生成单N-乙烯基化产物，而2.0当量的铜盐则提供双N-乙烯基化产物。对照实验表明3-（羟基亚氨基）吲哚-2-酮中的羰基对N-乙烯基化起重要作用。此外，在热条件下，可以将制备的N-乙烯基氧吲哚硝酮以良好的产率转化为螺硫辛多。
• Synthesis of <i>N</i>-Aryl Oxindole Nitrones through a Metal-Free Selective <i>N</i>-Arylation Process
  作者：Si-Yi Wu、Xiao-Pan Ma、Cui Liang、Dong-Liang Mo

  DOI：10.1021/acs.joc.6b02774

  日期：2017.3.17

  An efficient selective N-arylation of 3-(hydroxyimino)indolin-2-ones with diaryliodonium salts to prepare (Z)-N-aryl oxindole nitrones has been achieved under simple base-mediated conditions. The reaction tolerated a variety of diaryliodonium salts with diverse and sensitive functional groups. Studies on the oxime structures revealed that the pyrroline ring and carbonyl group in 3-(hydroxyimino)indolin-2-ones played important roles in the selective N-arylation process. The N-aryl oxindole nitrones could be prepared rapidly and easily at the gram scale.