p-fluorophenyllead triacetate | 53243-78-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: p-fluorophenyllead triacetate
• 英文别名: Tris(acetyloxy)(4-fluorophenyl)plumbane；[diacetyloxy-(4-fluorophenyl)plumbyl] acetate
• CAS: 53243-78-0
• 化学式: C₁₂H₁₃FO₆Pb
• 分子量: 479.43
• InChiKey: UXHDHOFISDPEGY-UHFFFAOYSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-fluorophenyllead triacetate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以78%的产率得到1-叠氮基-4-氟苯
  参考文献：
  名称：

  Huber, Marie-Luise; Pinhey, John T., Journal of the Chemical Society. Perkin transactions I, 1990, p. 721 - 722

  摘要：

  DOI：
• 作为产物：
  描述：

  lead(IV) acetate 、 双(4-氟苯基)汞 以 苯 为溶剂， 以49%的产率得到p-fluorophenyllead triacetate
  参考文献：
  名称：

  Kozyrod, Robert P.; Pinhey, John T., Australian Journal of Chemistry, 1985, vol. 38, p. 1155 - 1162

  摘要：

  DOI：

文献信息

• Aryl fluorides from the reaction of boron trifluoride with aryl-lead(IV) triacetates, which may be generated in situ from aryltrimethylsilanes, triarylboroxines, and arenes
  作者：Giuseppe V. De Meio、John T. Pinhey

  DOI：10.1039/c39900001065

  日期：——

  Aryl-lead(IV) triacetates react at room temperature with BF3·Et2O to give the corresponding aryl fluoride in moderate to good yields; triarylboroxines, electron-rich aryltrimethylsilanes, and some arenes, which yield aryl–lead(IV) triacetates in acid catalysed reactions with lead tetra-acetate, may be converted directly into aryl fluorides when stirred with lead tetra-acetate in BF3·Et2O.

  三乙酸芳基铅（IV）在室温下与BF 3 ·Et 2 O反应，以中等至良好的收率得到相应的芳基氟化物。三芳基硼氧烷，富电子芳基三甲基硅烷和一些芳烃，在四乙酸铅的酸催化反应中产生芳基乙酸铅（IV），当与四乙酸铅在BF 3 ·Et 2中搅拌时可直接转化为芳基氟化物哦
• Aryl fluoride syntheses involving reaction of aryllead triacetates with boron trifluoride-diethyl ether complex
  作者：Giuseppe De Meio、Jacqueline Morgan、John T. Pinhey

  DOI：10.1016/s0040-4020(01)88032-7

  日期：1993.9

  the corresponding aryl fluoride in moderate to good yields; triarylboroxines, electron rich aryltrimethylsilanes and some arenes, which yield aryllead triacetates in acid catalysed reactions with lead tetraacetate, are converted directly into aryl fluorides when stirred with lead tetraacetate in BF3.Et2O. An investigation of the mechanism of the fluoro-deplumbation reaction indicates that it probably

  三乙酸芳基铅（IV）在室温下与BF 3 .Et 2 O反应，以中等至良好的收率得到相应的芳基氟化物。三芳基硼氧烷，富电子的芳基三甲基硅烷和一些芳烃，在与四乙酸铅的酸催化反应中产生芳基三乙酸铅，当与四乙酸铅在BF 3 .Et 2 O中搅拌时，直接转化为芳基氟化物。反应表明它可能是通过酸催化的CPb键的杂合裂解而产生芳基阳离子而进行的。
• Reaction of organolead triacetates with 4-ethoxycarbonyl-2-methyloxazol-5-one. The synthesis of α-aryl and α-vinyl N-acetylglycine ethyl esters and their enzymic resolution
  作者：Jacqueline Morgan、John T. Pinhey

  DOI：10.1016/0040-4039(94)88529-x

  日期：1994.12

  An efficient synthesis of the moisture-sensitive compound, 4-ethoxycarbonyl-2-methyloxazol-5-one, has been achieved. This compound undergoes high-yielding arylation and vinylation at the 4-position with organolead triacetates to give compounds which in water are converted to α-aryl and α-vinyl N-acetylglycine ethyl esters. These α-substituted glycine derivatives may be kinetically resolved in very

  已经实现了对水分敏感化合物4-乙氧基羰基-2-甲基恶唑-5-酮的有效合成。该化合物在4-位用有机三乙酸铅进行高产率的芳基化和乙烯基化反应，得到在水中转化为α-芳基和α-乙烯基N-乙酰基甘氨酸乙酯的化合物。这些α-取代的甘氨酸衍生物可以通过相应的羧酸的酯基或酰胺官能团的酶水解以非常好的收率和高的对映体过量动力学地拆分。
• Chiral Bisphosphine-Catalyzed Asymmetric Staudinger/aza-Wittig Reaction: An Enantioselective Desymmetrizing Approach to Crinine-Type Amaryllidaceae Alkaloids
  作者：Hongzhi Yang、Jingyang Zhang、Sen Zhang、Zhengwen Xue、Shengkun Hu、Yi Chen、Yefeng Tang

  DOI：10.1021/jacs.4c02755

  日期：2024.5.22

  asymmetric Staudinger/aza-Wittig reaction of 2,2-disubstituted cyclohexane-1,3-diones is reported, enabling the facile access of a broad range of cis-3a-arylhydroindoles in high yields with excellent enantioselectivities. The key to the success of this work relies on the first application of chiral bisphosphine DuanPhos to the asymmetric Staudinger/aza-Wittig reaction. An effective reductive system has

  报道了前所未有的手性双膦催化的 2,2-二取代环己烷-1,3-二酮的不对称 Staudinger/aza-Wittig 反应，使得能够以高产率和优异的对映选择性轻松获得各种顺式-3a-芳基氢吲哚。这项工作成功的关键在于手性双膦 DuanPhos 首次应用于不对称 Staudinger/aza-Wittig 反应。已经建立了有效的还原系统来解决与手性双膦催化剂相关的具有挑战性的 P V =O/P III氧化还原循环。此外，还进行了全面的实验和计算研究，以阐明不对称反应的机理。利用新开发的化学方法，包括 (+)-powelline、(+)-buphanamine、(+)-vittatine 和 (+)-crinane 在内的几种 crinine 型石蒜科生物碱的对映选择性全合成已经非常简洁地完成和效率。
• Kozyrod, Robert P.; Morgan, Jacqueline; Pinhey, John T., Australian Journal of Chemistry, 1985, vol. 38, p. 1147 - 1154
  作者：Kozyrod, Robert P.、Morgan, Jacqueline、Pinhey, John T.

  DOI：——

  日期：——