6-chloro-1-methyl-2-oxo-N-phenylindol-3-imine oxide | 1407968-10-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 6-chloro-1-methyl-2-oxo-N-phenylindol-3-imine oxide
• CAS: 1407968-10-8
• 化学式: C₁₅H₁₁ClN₂O₂
• 分子量: 286.718
• InChiKey: YOVQLCHFISXHHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-chloro-1-methyl-2-oxo-N-phenylindol-3-imine oxide 、 丁炔二酸二甲酯 在 silica gel 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以62%的产率得到
  参考文献：
  名称：

  Construction of spiro[indoline]oxindoles through one-pot thermal-induced [3+2] cycloaddition/silica gel-promoted fragmentation sequence between isatin ketonitrones and electron-deficient alkynes

  摘要：

  One-pot thermal-induced [3+2] cycloaddition/silica gel-promoted fragmentation sequence between isatin ketonitrones and electron-deficient alkynes affords spiro[indoline]oxindoles in moderate to excellent yields along with good diastereoselectivities. The detailed mechanism of silica gel-promoted fragmentation has been clarified by experiment and DFT calculations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.062
• 作为产物：
  描述：

  6-chloro-3-diazo-1-methylindolin-2-one 、 亚硝基苯 在 silica gel 作用下， 以 neat (no solvent) 为溶剂， 反应 10.0h， 以90%的产率得到6-chloro-1-methyl-2-oxo-N-phenylindol-3-imine oxide
  参考文献：
  名称：

  Silica gel-promoted practical synthesis of oxindole–nitrones from diazooxindoles and nitrosoarenes under solvent-free conditions

  摘要：

  通过硅胶催化，开发了一种从二氮氧吲哚和亚硝基芳烃合成氧吲哚-亚硝基化合物的实用高效方法。

  DOI：

  10.1039/c5ra21874h

文献信息

• Copper-Catalyzed [3+2] Cycloaddition and Interrupted Fischer Indolization to Prepare Polycyclic Furo[2,3-b]indolines from <i>N</i> -Aryl Isatin Nitrones and Methylenecyclopropanes
  作者：Si-Yi Wu、Wei-Li Chen、Xiao-Pan Ma、Cui Liang、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1002/adsc.201801327

  日期：2019.3.5

  3‐b]indolines containing a cyclopropane ring have been prepared in moderate yields with high diastereoselectivity from N‐aryl isatin nitrones and methylenecyclopropanes using a copper‐catalyzed [3+2] cycloaddition and subsequent interrupted Fischer indolization strategy under mild reaction conditions. The obtained furo[2,3‐b]indolines were easily converted to piperidinone‐fused furo[2,3‐b]indolines by

  使用铜催化的[3 + 2]环加成反应，并随后在以下条件下中断的Fischer吲哚化策略下，已从N-芳基异丁烯腈和亚甲基环丙烷以中等收率和高非对映选择性制备了各种含环丙烷环的多环呋喃[2,3-b]二氢吲哚。反应条件温和。通过N-O键裂解选择性[1,3]重排，可将获得的呋喃[2,3-b]二氢吲哚轻松转化为哌啶酮-融合的呋喃[2,3-b]二氢吲哚。最后，通过手性辅助控制获得了两个手性多环呋喃[2,3-b]二氢吲哚。
• Yb(NTf2)3-catalyzed [3 + 3] cycloaddition between isatin ketonitrones and cyclopropanes to construct novel spiro[tetrahydro-1,2-oxazine]oxindoles
  作者：Hai-Bin Yang、Min Shi

  DOI：10.1039/c2ob26413g

  日期：——

  Yb(NTf2)3-catalyzed [3 + 3] cycloaddition between isatin ketonitrones and cyclopropanes is described. A variety of spiro[tetrahydro-1,2-oxazine]oxindoles were obtained in moderate to good yields along with good regioselectivities. This is the first example of the intermolecular [3 + 3] cycloaddition between ketone-derived nitrones and cyclopropanes.

  描述了 Yb(NTf2)3 催化的靛红酮硝酮和环丙烷之间的 [3 + 3] 环加成反应。以中等至良好的产率和良好的区域选择性获得了多种螺[四氢-1,2-恶嗪]吲哚。这是酮衍生的硝酮和环丙烷之间分子间[3 + 3]环加成的第一个例子。