[3-hydroxy-1-(3-methyl-2-buten-1-yl)-2-oxo-2,3-dihydroindol-3-yl]acetonitrile | 885117-72-6

• 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
• 英文名称: [3-hydroxy-1-(3-methyl-2-buten-1-yl)-2-oxo-2,3-dihydroindol-3-yl]acetonitrile
• CAS: 885117-72-6
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: LIIFBUGGEMSVQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [3-hydroxy-1-(3-methyl-2-buten-1-yl)-2-oxo-2,3-dihydroindol-3-yl]acetonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.25h， 生成 3a-hydroxy-1-methyl-8-(3-methyl-2-buten-1-yl)-1,2,3,3a,8a-hexahydropyrrolo[2,3-b]indole
  参考文献：
  名称：

  Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products

  摘要：

  This work describes a general protocol for the oxidation of indole and oxindole derivatives with dimethyldioxirane to give 3-hydroxyoxindoles present in many natural products. This strategy allowed us to synthesize the natural product 1, to carry out the first total synthesis of 4, a formal total synthesis of donaxaridine (5) and to achieve the synthesis of pyrroloindoline 8, a debromo analogue of the natural product flustraminol B (7). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.036
• 作为产物：
  描述：

  吲哚-3-乙腈 在 碳酸氢钠 盐酸 、 Oxone 、 disodium ethylenediaminetetraacetic acid 、 potassium carbonate 、 二甲基亚砜 、 丙酮 作用下， 以 水 、 丙酮 为溶剂， 反应 17.5h， 生成 [3-hydroxy-1-(3-methyl-2-buten-1-yl)-2-oxo-2,3-dihydroindol-3-yl]acetonitrile
  参考文献：
  名称：

  Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products

  摘要：

  This work describes a general protocol for the oxidation of indole and oxindole derivatives with dimethyldioxirane to give 3-hydroxyoxindoles present in many natural products. This strategy allowed us to synthesize the natural product 1, to carry out the first total synthesis of 4, a formal total synthesis of donaxaridine (5) and to achieve the synthesis of pyrroloindoline 8, a debromo analogue of the natural product flustraminol B (7). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.036

文献信息

• Nickel‐Catalyzed Cyanoalkylation of Ketone Derivatives
  作者：Anaïs Coffinet、Vincent Levacher、Isabelle Gillaizeau、Jean‐François Brière、Sylvain Oudeyer

  DOI：10.1002/adsc.202201147

  日期：2023.1.24

  Although the metal-based catalyzed cyanomethylation of aldehydes is well-developed, a similar approach to ketones with acetonitrile derivatives remains a challenge. Thanks to Tolman type complexes, NiII-complexes with a pyridine(dicarboxamide) pincer ligand, an alternative metal-catalyzed (1–5 mol% catalyst) cyanomethylation of an array of isatins and activated ketones is reported at room temperature

  尽管基于金属的催化醛类氰甲基化反应已经很成熟，但用乙腈衍生物对酮类进行类似的催化反应仍然是一个挑战。多亏了 Tolman 型配合物，Ni II配合物与吡啶（二甲酰胺）钳形配体，一种替代的金属催化（1-5 mol% 催化剂）在室温下对一系列靛红和活化酮进行氰甲基化。不仅使用弱酸性乙腈，而且使用更具挑战性的取代烷基氰化物亲核试剂，都获得了高分离产率（高达 99%）。原位生成的假定离子对催化剂 [NiCR 2 CN] - Cat +可能受益于阳离子部分（Cs +或n -Bu 4 N + ) 以促进它们的形成和催化活性。
• Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products
  作者：Oscar R. Suárez-Castillo、Maricruz Sánchez-Zavala、Myriam Meléndez-Rodríguez、Luis E. Castelán-Duarte、Martha S. Morales-Ríos、Pedro Joseph-Nathan

  DOI：10.1016/j.tet.2006.01.036

  日期：2006.3

  This work describes a general protocol for the oxidation of indole and oxindole derivatives with dimethyldioxirane to give 3-hydroxyoxindoles present in many natural products. This strategy allowed us to synthesize the natural product 1, to carry out the first total synthesis of 4, a formal total synthesis of donaxaridine (5) and to achieve the synthesis of pyrroloindoline 8, a debromo analogue of the natural product flustraminol B (7). (c) 2006 Elsevier Ltd. All rights reserved.