2-diphenylphosphanyl benzoic acid ethyl ester

• 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: 2-diphenylphosphanyl benzoic acid ethyl ester
• 英文别名: ethyl 2-(diphenylphosphanyl)benzoate；o-Ph2PC6H4COOC2H5；ethyl o-diphenylphosphinobenzoate；ethyl diphenylphosphinobenzoate；ethyl 2-diphenylphosphanylbenzoate
• 化学式: C₂₁H₁₉O₂P
• 分子量: 334.354
• InChiKey: FRVBNDJKPAYVRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-diphenylphosphanyl benzoic acid ethyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 2-二苯基膦苯甲酸
  参考文献：
  名称：

  METHOD FOR SYNTHESIS OF O-DIPHENYLPHOSPHINOBENZOIC ACID

  摘要：

  本发明涉及一种合成o-二苯基膦基苯甲酸的方法，包括以下步骤：使用氯二苯基膦作为起始原料，将氯二苯基膦和碱金属加入溶剂中进行裂解，产生二苯基膦碱金属盐，然后加入o-氯苯甲酸盐或o-氯苯甲酸酯进行偶联反应，生成二苯基膦基苯甲酸盐或二苯基膦基苯甲酸酯，经水解后得到o-二苯基膦基苯甲酸。通过使用本方法，在大气压下，温度高于0°C时可以制备o-二苯基膦基苯甲酸。该方法操作安全稳定，节约能源，适合大规模生产。

  公开号：

  US20110077426A1
• 作为产物：
  描述：

  2-碘苯甲酸乙酯, 、 二苯基膦 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 三乙胺 作用下， 以 乙腈 为溶剂， 以34%的产率得到2-diphenylphosphanyl benzoic acid ethyl ester
  参考文献：
  名称：

  Mechanistic Investigation of the Staudinger Ligation

  摘要：

  The Staudinger ligation of azides and phosphines has found widespread use in the field of chemical biology, but the mechanism of the transformation has not been characterized in detail. In this work, we undertook a mechanistic study of the Staudinger ligation with a focus on factors that affect reaction kinetics and on the identification of intermediates. The Staudinger ligation with alkyl azides was second-order overall and proceeded more rapidly in polar, protic solvents. Hammett analyses demonstrated that electron-donating substituents on the phosphine accelerate the overall reaction. The electronic and steric properties of the ester had no significant impact on the overall rate but did affect product ratios. Finally, the structure of an intermediate that accumulates under anhydrous conditions was identified. These findings establish a platform for optimizing the Staudinger ligation for expanded use in biological applications.

  DOI：

  10.1021/ja044461m

文献信息

• PREPARATION OF DIAZO AND DIAZONIUM COMPOUNDS
  申请人：Raines Ronald Thaddeus

  公开号：US20100125132A1

  公开（公告）日：2010-05-20

  A method for making diazo-compounds, diazonium salts thereof and other protected forms of these compounds. Diaz-compounds are prepared by reaction of a tertiary phosphine reagent carrying a reactive carbonyl group with an azide. The reaction can also generate an acyl triazene which can be converted thermally or by addition of base to form the diazo-compound or the acyl triazene can be isolated. The method is particularly useful for conversion of azides carrying one or more electron withdrawing groups to diazo-compounds. The method can be carried out in aqueous medium under mild conditions and is particularly useful for conversion of azido sugars to diazo-compound and diazonium salts thereof under physiological conditions. Tertiary phosphine reagents, particularly those that are water-soluble, and precursors for preparation of the reagents are provided.

  一种制备重氮化合物、其重氮盐和这些化合物的其他保护形式的方法。通过将携带反应性羰基基团的三级膦试剂与偶氮化物反应来制备重氮化合物。该反应还可以生成酰基三氮烯，可以通过热转化或加入碱来形成重氮化合物，或者可以分离出酰基三氮烯。该方法特别适用于将携带一个或多个电子吸引基团的偶氮化物转化为重氮化合物。该方法可以在温和条件下在水性介质中进行，并且特别适用于在生理条件下将偶氮糖转化为重氮化合物和其重氮盐。提供了三级膦试剂，特别是那些水溶性的试剂，以及用于制备这些试剂的前体。
• Cationic Palladium η³-Allyl Complexes with Hemilabile P,O-Ligands:  Synthesis and Reactivity. Insertion of Ethylene into the Pd−Allyl Function
  作者：Stefan Mecking、Wilhelm Keim

  DOI：10.1021/om960061z

  日期：1996.5.28

  Cationic palladium allyl complexes [(η3-C3H5)Pd(κ2P∧O)]+SbF6- (2[SbF6], P∧O ≡ Ph2P(CH2)2C(O)OEt; 3[SbF6], o-Ph2PC6H4C(O)OEt; 4[SbF6], Ph2P(CH2)2P(O)Ph2) have been prepared. In all complexes the oxygen donor can be displaced by other ligands such as carbon monoxide and ethylene. Displacement of an ester donor occurs much more readily than displacement of the phosphine oxide function. Above 0 °C, the

  阳离子钯络合物烯丙基[（η 3 -C 3 H ^ 5）的Pd（κ 2 P ∧ Ò）] +的SbF 6 - （2 [的SbF 6 ]，P ∧ ö ≡博士2 P（CH 2）2 C（Ò） OEt; 3 [SbF 6 ]，o -Ph 2 P C 6 H 4 C（O）OEt; 4 [SbF 6 ]，Ph 2 P已经制备了（CH 2）2 P（O）Ph 2。在所有配合物中，供氧体可以被其他配体（例如一氧化碳和乙烯）取代。酯供体的置换比氧化膦功能的置换更容易发生。高于0℃，将得到的乙烯配合物[（η 3 -C 3 H ^ 5）的Pd（C 2 H ^ 4）（κ 1 P ~O）] +反应，得到（1,2,5-η 3） -戊-1-烯-5-基配合物[（H 2 ç CH（CH 2）3的Pd（κ 2 P ∧O）] +。的速率常数如ķ（17℃）=（2.27±0.11）×10 - 4个小号- 1被确定为P，O≡博士2 P（CH
• Preparation of diazo and diazonium compounds
  申请人：Wisconsin Alumni Research Foundation

  公开号：US08350014B2

  公开（公告）日：2013-01-08

  A method for making diazo-compounds, diazonium salts thereof and other protected forms of these compounds. Diaz-compounds are prepared by reaction of a tertiary phosphine reagent carrying a reactive carbonyl group with an azide. The reaction can also generate an acyl triazene which can be converted thermally or by addition of base to form the diazo-compound or the acyl triazene can be isolated. The method is particularly useful for conversion of azides carrying one or more electron withdrawing groups to diazo-compounds. The method can be carried out in aqueous medium under mild conditions and is particularly useful for conversion of azido sugars to diazo-compound and diazonium salts thereof under physiological conditions. Tertiary phosphine reagents, particularly those that are water-soluble, and precursors for preparation of the reagents are provided.

  一种制备重氮化合物、重氮盐及这些化合物的其他保护形式的方法。通过将带有反应性羰基基团的三级膦试剂与叠氮化合物反应制备重氮化合物。该反应也可以生成酰基三氮烯，可通过热转化或加入碱来形成重氮化合物，或可将酰基三氮烯分离。该方法特别适用于将带有一个或多个电子吸引基团的叠氮化合物转化为重氮化合物。该方法可在温和条件下在水介质中进行，并且特别适用于在生理条件下将叠氮糖转化为重氮化合物和重氮盐。提供了三级膦试剂，特别是水溶性的试剂及其制备前体。
• Diaryl phosphine compounds
  申请人：Raines Ronald Thaddeus

  公开号：US08871916B2

  公开（公告）日：2014-10-28

  A method for making diazo-compounds, diazonium salts thereof and other protected forms of these compounds. Diazo-compounds are prepared by reaction of a tertiary phosphine reagent carrying a reactive carbonyl group with an azide. The reaction can also generate an acyl triazene which can be converted thermally or by addition of base to form the diazo-compound or the acyl triazene can be isolated. The method is particularly useful for conversion of azides carrying one or more electron withdrawing groups to diazo-compounds. The method can be carried out in aqueous medium under mild conditions and is particularly useful for conversion of azido sugars to diazo-compounds and diazonium salts thereof under physiological conditions. Tertiary phosphine reagents, particularly those that are water-soluble, and precursors for preparation of the reagents are provided.

  一种制备重氮化合物、其重氮盐和其他保护形式的方法。通过三级膦试剂带有反应性羰基基团与叠氮化物反应制备重氮化合物。该反应还可以生成酰基三氮烯，可以通过热转化或加入碱来形成重氮化合物，或者可以分离出酰基三氮烯。该方法特别适用于将带有一个或多个电子吸引基团的叠氮化合物转化为重氮化合物。该方法可以在温和条件下在水介质中进行，特别适用于在生理条件下将叠氮糖转化为重氮化合物和其重氮盐。提供了三级膦试剂，特别是水溶性试剂和制备试剂的前体。
• Preparation of Diazo and Diazonium Compounds
  申请人：RAINES Ronald Thaddeus

  公开号：US20130203974A1

  公开（公告）日：2013-08-08

  A method for making diazo-compounds, diazonium salts thereof and other protected forms of these compounds. Diaz-compounds are prepared by reaction of a tertiary phosphine reagent carrying a reactive carbonyl group with an azide. The reaction can also generate an acyl triazene which can be converted thermally or by addition of base to form the diazo-compound or the acyl triazene can be isolated. The method is particularly useful for conversion of azides carrying one or more electron withdrawing groups to diazo-compounds. The method can be carried out in aqueous medium under mild conditions and is particularly useful for conversion of azido sugars to diazo-compound and diazonium salts thereof under physiological conditions. Tertiary phosphine reagents, particularly those that are water-soluble, and precursors for preparation of the reagents are provided.

  一种制备重氮化合物、其重氮盐和这些化合物的其他保护形式的方法。通过将带有反应性羰基基团的三级膦试剂与叠氮化物反应来制备重氮化合物。该反应也可以生成酰基三氮烯，可以通过热转化或加入碱来形成重氮化合物，或者可以分离出酰基三氮烯。该方法特别适用于将带有一个或多个电子提取基团的叠氮化合物转化为重氮化合物。该方法可以在温和条件下在水介质中进行，特别适用于在生理条件下将叠氮糖转化为重氮化合物和其重氮盐。提供了三级膦试剂，特别是那些水溶性的试剂和制备试剂的前体。