tert-butyl 3-oxo-5-phenyl-2-(triphenylphosphoranylidene)-(E)-4-pentenoate | 83207-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl 3-oxo-5-phenyl-2-(triphenylphosphoranylidene)-(E)-4-pentenoate
• 英文别名: tert-butyl (E)-3-oxo-5-phenyl-2-(triphenyl-lambda5-phosphanylidene)pent-4-enoate；tert-butyl (E)-3-oxo-5-phenyl-2-(triphenyl-λ5-phosphanylidene)pent-4-enoate
• CAS: 83207-71-0
• 化学式: C₃₃H₃₁O₃P
• 分子量: 506.581
• InChiKey: CUGGWPQOZLNKLP-OCOZRVBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-oxo-5-phenyl-2-(triphenylphosphoranylidene)-(E)-4-pentenoate 在 三氟乙酸 作用下， 反应 2.18h， 生成
  参考文献：
  名称：

  Charge-directed conjugate addition reactions in the preparation of substituted methyl ketones

  摘要：

  DOI：

  10.1021/jo00146a025
• 作为产物：
  描述：

  氯乙酸叔丁酯 以 苯 为溶剂， 反应 48.67h， 生成 tert-butyl 3-oxo-5-phenyl-2-(triphenylphosphoranylidene)-(E)-4-pentenoate
  参考文献：
  名称：

  Charge-directed conjugate addition reactions in the preparation of substituted methyl ketones

  摘要：

  DOI：

  10.1021/jo00146a025

文献信息

• A New Synthesis of Triphenylphosphorane Ylide Precursors to α-Keto Amide/Ester and Tricarbonyl Units via Horner-Wadsworth-Emmons Reaction
  作者：Kie-Seung Lee

  DOI：10.5012/bkcs.2010.31.10.2776

  日期：2010.10.20

  compounds under mild reaction conditions to afford β,γ-unsaturated α-keto triphenylphorane ylides in good to excellent yields, which were hydrogenated over Pd-C (10%)/H 2 (1 atm) to give the corresponding α-keto triphenylphorane ylides in quasi-quantitative yields. These triphenyphosphorane ylides have been utilized as the precursors to α-keto amide/ester and vicinal tricarbonyl units in Wasserman's synthetic

  新开发的 Homer-Wadsworth-Emmons (HWE) 试剂 5 具有三苯基正膦叶立德亚基，在温和的反应条件下易于与各种羰基化合物缩合，以良好至极好的收率提供 β,γ-不饱和 α-酮基三苯基佛兰叶立德，在 Pd- 上氢化C (10%)/H 2 (1 atm) 以准定量产率得到相应的 α-酮基三苯基佛兰叶立德。在 Wasserman 的合成方案中，这些三苯基正膦叶立德已被用作 α-酮酰胺/酯和连位三羰基单元的前体，并且以前仅由羧酸/酰氯制备。
• 습윤 옥손을 이용한 비시날 트라이카보닐 화합물의 제조방법
  申请人：WOOSUK UNIVERSITY 우석대학교 산학협력단(220040061210) BRN ▼402-82-15573

  公开号：KR20220124912A

  公开（公告）日：2022-09-14

  본 발명은 습윤 옥손을 이용한 비시날 트라이카보닐 화합물의 제조방법에 관한 것이다. 본 발명에 따르면 다량의 유기용매와 건조제를 사용하지 않고 보다 효율적으로 비시날 트라이카보닐 화합물을 제조할 수 있다.

  这项发明涉及使用湿润的乙醇作为制备双(三氟甲基)苯基三甲酸酯化合物的溶剂的方法。根据本发明，可以更有效地制备双(三氟甲基)苯基三甲酸酯化合物，而无需使用大量的有机溶剂和干燥剂。
• Selective Oxidation of Phosphorus Ylides by Dimethyldioxirane. Application to the Formation of Vicinal Tricarbonyls
  作者：Harry H. Wasserman、Carmen M. Baldino、Steven J. Coats

  DOI：10.1021/jo00130a023

  日期：1995.12

  Dimethyldioxirane (DMD) has proven to be an effective reagent for the selective conversion of phosphoranylidene intermediates 4 to the corresponding vicinal tricarbonyls 5. Unlike existing oxidation protocols which employ relatively vigorous conditions, this transformation is conducted rapidly at low temperature under neutral conditions, without the necessity of an aqueous workup. Selective oxidation of the phosphorus ylides in the presence of a variety of sensitive functionality was achieved by lowering the reaction temperature and controlling the concentration of oxidant.
• A practical procedure for the selective oxidation of phosphorus keto ylides to vicinal tricarbonyls using moist magnesium monoperoxyphthalate (MMPP) in dichloromethane at ambient temperature
  作者：Kieseung Lee、Jin-Mo Im

  DOI：10.1016/s0040-4039(00)02280-2

  日期：2001.2

  Unsupported, moist magnesium monoperoxyphthalate (MMPP) was found to oxidize various phosphorus keto ylides to the corresponding vicinal tricarbonyls selectively in dichloromethane at ambient temperature in good to excellent yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
• COOKE, M. P. ,, JR;BURMAN, D. L., J. ORG. CHEM., 1982, 47, N 25, 4955-4963
  作者：COOKE, M. P. ,, JR、BURMAN, D. L.

  DOI：——

  日期：——