tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)carbamate | 1850305-80-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)carbamate
• 英文别名: Tert-butyl N-[3-(tetramethyl-1,3,2-dioxaborolan-2-YL)propyl]carbamate；tert-butyl N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]carbamate
• CAS: 1850305-80-4
• 化学式: C₁₄H₂₈BNO₄
• 分子量: 285.192
• InChiKey: MQRYONXVKZQEAC-UHFFFAOYSA-N

物化性质

• 沸点：
  351.7±25.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  对氟苯甲酰胺 、 tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)carbamate 在 二叔丁基过氧化物 、 C₂₁H₂₆N₂O₂ 、 copper diacetate 、 sodium trimethylsilanolate 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以76%的产率得到tert-butyl N-(3-(4-fluorobenzamido)propyl)carbamate
  参考文献：
  名称：

  铜催化的一级和二级烷基硼酸酯的酰胺化反应

  摘要：

  报道了功能化烷基硼酸酯与伯酰胺的氧化铜催化交叉偶联。通过鉴定适当的二酮亚胺配体，已经开发了使伯烷基硼酸酯和仲烷基硼酸酯与各种伯酰胺（包括乙酰胺）有效偶联的条件。

  DOI：

  10.1002/chem.201603677
• 作为产物：
  描述：

  N-BOC-GAMMA-氨基丁酸 在 copper acetylacetonate 、 lithium hydroxide monohydrate 、 magnesium chloride 、 N,N'-二异丙基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)carbamate
  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

• Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ-Amino Boronic Esters
  作者：Adam Noble、Riccardo S. Mega、Daniel Pflästerer、Eddie L. Myers、Varinder K. Aggarwal

  DOI：10.1002/anie.201712186

  日期：2018.2.19

  The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single-electron reduction of an α-boryl radical intermediate to the corresponding anion. The reaction is amenable to a diverse range of substrates, including α-amino, α-oxy, and

  描述了通过将羧酸直接脱羧基加成到乙烯基硼酸酯上来合成烷基硼酸酯。该反应在温和的光氧化还原催化下进行，涉及α-硼基自由基中间体前所未有的单电子还原成相应的阴离子。该反应适用于多种底物，包括α-氨基、α-氧基和烷基羧酸，从而提供了一种快速获取具有潜在生物学重要性的含硼分子的新方法。
• Copper-Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β-and γ-Amino­alkyl)boronic Esters
  作者：Nina Ursinyova、Robin B. Bedford、Timothy Gallagher

  DOI：10.1002/ejoc.201501492

  日期：2016.2

  Abstract Cyclic sulfamidates undergo borylation under copper‐catalyzed conditions using B2pin2 to give enantiomerically (and diasteromerically) defined (aminoalkyl)boronic esters. External iodide is essential, but the intermediacy of simple alkyl iodides has been excluded; N‐sulfated intermediates are key in the borylation sequence. Based on stereochemical studies and trapping experiments, the involvement

  摘要 环状磺酰胺在铜催化条件下使用 B2pin2 进行硼酸化，得到对映异构（和非对映异构）定义的（氨基烷基）硼酸酯。外部碘化物是必不可少的，但简单的烷基碘化物已被排除在外；N-硫酸化中间体是硼酸化序列中的关键。基于立体化学研究和捕获实验，在这些铜催化条件下碳中心自由基的参与似乎是可能的。
• 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。
• Visible‐Light‐Promoted Reaction of <i>N</i> ‐Hydroxyphthalimide Esters with Vinyl Boronic Pinacol Ester
  作者：Petros L. Gkizis、Ierasia Triandafillidi、Naya A. Stini、Charikleia S. Batsika、Christoforos G. Kokotos

  DOI：10.1002/ejoc.202300152

  日期：——

  A light-driven protocol to access alkyl boronic acid pinacol esters from vinyl boronate using N-hydroxyphthalimide esters as the alkyl generator was developed. A good substrate scope was examined, demonstrating good to high yields and excellent functional group tolerance.

  开发了一种光驱动方案，使用N-羟基邻苯二甲酰亚胺酯作为烷基生成剂，从硼酸乙烯酯中获取烷基硼酸频哪醇酯。检查了良好的底物范围，证明了良好的高产率和出色的官能团耐受性。
• Cu-Catalyzed Decarboxylative Borylation
  作者：Jie Wang、Ming Shang、Helena Lundberg、Karla S. Feu、Scott J. Hecker、Tian Qin、Donna G. Blackmond、Phil S. Baran

  DOI：10.1021/acscatal.8b02928

  日期：2018.10.5

  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.