potassium (5-((tert-butyldiphenylsilyl)oxy)pent-1-yn-1-yl)trifluoroborate | 1370340-53-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: potassium (5-((tert-butyldiphenylsilyl)oxy)pent-1-yn-1-yl)trifluoroborate
• 英文别名: potassium (5-(tert-butyldiphenylsilyloxy)pent-1-ynyl)trifluoroborate；Potassium;5-[tert-butyl(diphenyl)silyl]oxypent-1-ynyl-trifluoroboranuide
• CAS: 1370340-53-6
• 化学式: C₂₁H₂₅BF₃OSi*K
• 分子量: 428.419
• InChiKey: UQGXSPUOGGHHIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  potassium (5-((tert-butyldiphenylsilyl)oxy)pent-1-yn-1-yl)trifluoroborate 在 (R)-3,3'-diiodo-6,6'-bis(trifluoromethyl)-[1,1'-binaphthalene]-2,2'-diol 、 C.I.酸性橙108 、 lithium iodide 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Organocatalytic Enantioselective Conjugate Alkynylation of β-Aminoenones: Access to Chiral β-Alkynyl-β-Amino Carbonyl Derivatives

  摘要：

  Readily available potassium alkynyltrifluoroborates were used for organocatalytic asymmetric conjugate alkynylation of beta-enaminones. The interception of a modified binaphthol catalyst and in situ generated organodifluoroboranes proved important to access functionalized beta-alkynyl-beta-amino carbonyls and derivatives with improved chemo-reactivity and enantio-induction. Mechanistic studies revealed the impact of molecular sieves on efficiency and stereocontrol. The products undergo additional functionalization to yield a diverse set of valuable beta-alkynyl-beta-amino carbonyl scaffolds.

  DOI：

  10.1021/acs.orglett.0c02394
• 作为产物：
  描述：

  tert-butyl-pent-4-ynyloxy-diphenyl-silane 在 正丁基锂 、 硼酸三异丙酯 、 甲醇 、 二氟化氢钾 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 4.7h， 以66%的产率得到potassium (5-((tert-butyldiphenylsilyl)oxy)pent-1-yn-1-yl)trifluoroborate
  参考文献：
  名称：

  通过无痕 Petasis 反应直接合成艾伦烯

  摘要：

  报道了通过羟基醛或酮与炔基三氟硼酸盐的 2-硝基苯磺酰肼介导的偶联来一锅法合成丙二烯。这种温和的过程涉及原位形成磺酰腙，该磺酰腙与炔基三氟硼酸盐反应生成瞬态炔丙基酰肼物质。这种不稳定的酰肼通过中间体单烷基二嗪分解，通过烯烃步行机制产生丙二烯产物。

  DOI：

  10.1021/ja301489n

文献信息

• Electrochemical Oxidation Enables Regioselective 1,3-Hydroxyfunctionalization of Cyclopropanes
  作者：Wei Sheng、Xuejin Huang、Jianhua Cai、Ye Zheng、Yuxi Wen、Chunlan Song、Jiakun Li

  DOI：10.1021/acs.orglett.3c02309

  日期：2023.8.25

  significant challenge, as they can currently be obtained through multiple synthetic steps. Herein, we report a general and efficient 1,3-hydroxyfunctionalization of arylcyclopropanes by electrochemical oxidation with a strategic choice of nucleophiles and H2O. 1,3-Amino alcohols, 1,3-alkynyl alcohols, 1,3-hydroxyesters, and 1,3-halo alcohols are achieved with high levels of chemo- and regio-selectivity, opening

  直接构建 1,3-羟基官能化分子仍然是一个重大挑战，因为它们目前可以通过多个合成步骤获得。在此，我们报告了通过电化学氧化，策略性选择亲核试剂和 H 2 O，对芳基环丙烷进行通用且有效的 1,3-羟基官能化。1,3-氨基醇、1,3-炔醇、1,3-羟基酯和1,3-卤代醇具有高水平的化学和区域选择性，为1,3-双官能化反应开辟了新的维度。
• SAMDI Mass Spectrometry-Enabled High-Throughput Optimization of a Traceless Petasis Reaction
  作者：Abdallah B. Diagne、Shuheng Li、Gregory A. Perkowski、Milan Mrksich、Regan J. Thomson

  DOI：10.1021/acscombsci.5b00131

  日期：2015.11.9

  Development of the self-assembled monolayer/MALDI mass spectrometry (SAMDI) platform to enable a high-throughput optimization of a traceless Petasis reaction is described. More than 1800 unique reactions were conducted simultaneously on an array of self-assembled monolayers of alkanethiolates on gold to arrive at optimized conditions, which were then successfully transferred to the solution phase. The utility of this reaction was validated by the efficient synthesis of a variety of di- and trisubstituted allenes.
• Organocatalytic Enantioselective Conjugate Alkynylation of β-Aminoenones: Access to Chiral β-Alkynyl-β-Amino Carbonyl Derivatives
  作者：Jian-Fei Wang、Xin Meng、Chao-Huan Zhang、Chuan-Ming Yu、Bin Mao

  DOI：10.1021/acs.orglett.0c02394

  日期：2020.10.2

  Readily available potassium alkynyltrifluoroborates were used for organocatalytic asymmetric conjugate alkynylation of beta-enaminones. The interception of a modified binaphthol catalyst and in situ generated organodifluoroboranes proved important to access functionalized beta-alkynyl-beta-amino carbonyls and derivatives with improved chemo-reactivity and enantio-induction. Mechanistic studies revealed the impact of molecular sieves on efficiency and stereocontrol. The products undergo additional functionalization to yield a diverse set of valuable beta-alkynyl-beta-amino carbonyl scaffolds.
• A Direct Synthesis of Allenes by a Traceless Petasis Reaction
  作者：Devon A. Mundal、Kelly E. Lutz、Regan J. Thomson

  DOI：10.1021/ja301489n

  日期：2012.4.4

  A one-pot synthesis of allenes by the 2-nitrobenzenesulfonylhydrazide-mediated coupling of hydroxyaldehydes or ketones with alkynyl trifluoroborate salts is reported. This mild process involves in situ formation of a sulfonylhydrazone that reacts with alkynyl trifluoroborates to generate a transient propargylic hydrazide species. Decomposition of this unstable hydrazide via an intermediate monoalkyldiazine

  报道了通过羟基醛或酮与炔基三氟硼酸盐的 2-硝基苯磺酰肼介导的偶联来一锅法合成丙二烯。这种温和的过程涉及原位形成磺酰腙，该磺酰腙与炔基三氟硼酸盐反应生成瞬态炔丙基酰肼物质。这种不稳定的酰肼通过中间体单烷基二嗪分解，通过烯烃步行机制产生丙二烯产物。