1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl3-{[(tert-butoxy)carbonyl]amino}-3-methylbutanoate | 2244699-99-6

• 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: 1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl3-{[(tert-butoxy)carbonyl]amino}-3-methylbutanoate
• 英文别名: (1,3-dioxoisoindol-2-yl) 3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 2244699-99-6
• 化学式: C₁₈H₂₂N₂O₆
• 分子量: 362.382
• InChiKey: LHBKUCFGFMKWSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  102.01
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl3-{[(tert-butoxy)carbonyl]amino}-3-methylbutanoate 、 联硼酸频那醇酯 在 copper acetylacetonate 、 lithium hydroxide monohydrate 、 magnesium chloride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以70%的产率得到
  参考文献：
  名称：

  Cu-Catalyzed Decarboxylative Borylation

  摘要：

  A simple method for the conversion of carboxylic acids to boronic esters via redox-active esters (RAEs) is reported using copper catalysis. The scope of this transformation is broad, and compared with the known protocols available, it represents the most inexpensive, rapid, and operationally simple option. In addition to a full exploration of the scope, a kinetic study was performed to elucidate substrate and reagent concentration dependences.

  DOI：

  10.1021/acscatal.8b02928
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 N-Boc-3-氨基-3-甲基丁酸 在 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl3-{[(tert-butoxy)carbonyl]amino}-3-methylbutanoate
  参考文献：
  名称：

  Cu-Catalyzed Decarboxylative Borylation

  摘要：

  A simple method for the conversion of carboxylic acids to boronic esters via redox-active esters (RAEs) is reported using copper catalysis. The scope of this transformation is broad, and compared with the known protocols available, it represents the most inexpensive, rapid, and operationally simple option. In addition to a full exploration of the scope, a kinetic study was performed to elucidate substrate and reagent concentration dependences.

  DOI：

  10.1021/acscatal.8b02928

文献信息

• A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines
  作者：Shengyang Ni、Natalia M. Padial、Cian Kingston、Julien C. Vantourout、Daniel C. Schmitt、Jacob T. Edwards、Monika M. Kruszyk、Rohan R. Merchant、Pavel K. Mykhailiuk、Brittany B. Sanchez、Shouliang Yang、Matthew A. Perry、Gary M. Gallego、James J. Mousseau、Michael R. Collins、Robert J. Cherney、Pavlo S. Lebed、Jason S. Chen、Tian Qin、Phil S. Baran

  DOI：10.1021/jacs.9b02238

  日期：2019.4.24

  Historically accessed through two-electron, anionic chemistry, ketones, alcohols, and amines are of foundational importance to the practice of organic synthesis. After placing this work in proper historical context, this Article reports the development, full scope, and a mechanistic picture for a strikingly different way of forging such functional groups. Thus, carboxylic acids, once converted to redox-active

  历史上通过二电子、阴离子化学、酮、醇和胺进行访问对于有机合成的实践具有基础重要性。在将这项工作置于适当的历史背景下之后，本文报告了形成此类功能组的截然不同的方式的发展、全范围和机械图。因此，羧酸一旦转化为氧化还原活性酯 (RAE)，就可以用作形式上与其他羧酸衍生物（生产酮）、亚胺（生产苄胺）或醛（生产醇）的亲核偶联伙伴。这些反应一致温和，操作简单，并且在酮合成的情况下，范围很广（包括一些简化合成问题和平行合成的应用）。最后，
• Electrochemically promoted decarboxylative borylation of alkyl N-hydroxyphthalimide esters
  作者：Jian-Jun Dai、Xin-Xin Teng、Wen Fang、Jun Xu、Hua-Jian Xu

  DOI：10.1016/j.cclet.2021.09.011

  日期：2022.3

  An electrochemically promoted decarboxylative borylation reaction is reported. The reaction proceeds under mild conditions in an undivided cell without use of transition metal- or photo-catalysts. The key feature of the reaction is the compatibility of diboron reagents with the electrochemical conditions. This reaction exhibits broad substrate scope, good functional group tolerability, and easy scalability

  报道了一种电化学促进的脱羧硼化反应。该反应在温和条件下在未分裂的电池中进行，无需使用过渡金属或光催化剂。该反应的关键特征是二硼试剂与电化学条件的相容性。该反应具有广泛的底物范围、良好的官能团耐受性和易于扩展的特点。