methyl 3-(phenylphosphanyl)propanoate | 6798-65-8

• 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: methyl 3-(phenylphosphanyl)propanoate
• 英文别名: β-Carbomethoxyaethylphenylphosphin；methyl 3-phenylphosphanylpropanoate
• CAS: 6798-65-8
• 化学式: C₁₀H₁₃O₂P
• 分子量: 196.186
• InChiKey: RXDJAXUIXVLBHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-Phenylphosphanyl-propionic acid methyl ester; compound with borane 在 二乙胺 作用下， 生成 methyl 3-(phenylphosphanyl)propanoate
  参考文献：
  名称：

  Hydrophosphination of α,β-unsaturated esters by primary phosphine-boranes; a useful entry to symmetrical and unsymmetrical phosphine-boranes

  摘要：

  The reactivity of primary phosphine-boranes RPH(2) . BH3 (R = Ph and Me) towards CH2=CHCO(2)Me and CH2=CHP(O)(OMe)(2) is discussed. Hydrophosphination is the major process. The presence of the free phosphine (0-20%) in the crude media indicates that a competitive hydroboration reaction also occurs. The P-H addition was found to be controllable to give, in reasonable yields. either the mono or the bis-adducts. All the adducts are stable and are fully characterized, The preparation of an unsymmetrical bis-adduct is also presented. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00247-5

文献信息

• A bench-stable copper photocatalyst for the rapid hydrophosphination of activated and unactivated alkenes
  作者：Steven G. Dannenberg、Rory Waterman

  DOI：10.1039/d0cc06570f

  日期：——

  that have never before been reported with an air-stable catalyst or at ambient temperature. The commercial availability, ease of use, and broad substrate scope of compound 1 make hydrophosphination more available to synthetic chemists.

  Cu（acac）2（1）是用于烯烃加氢磷酸化的高活性催化剂。光催化条件很关键，并且可以用空气稳定的催化剂或在环境温度下从未报道过的未活化的底物提供高转化率。化合物1的商业可得性，易用性和广泛的底物范围使加氢磷酸化更易于合成化学家使用。
• A Study of Two Highly Active, Air-Stable Iron(III)-μ-Oxo Precatalysts: Synthetic Scope of Hydrophosphination using Phenyl- and Diphenylphosphine
  作者：Kimberley J. Gallagher、Maialen Espinal-Viguri、Mary F. Mahon、Ruth L. Webster

  DOI：10.1002/adsc.201501179

  日期：2016.7.28

  The importance of phosphines in synthetic chemistry cannot be underestimated. Catalytic hydrophosphination offers an ideal method to prepare P−C bonds without the need for harsh reaction conditions or stoichiometric amounts of waste by‐product. We herein report our studies into two biocompatible iron(III) complexes in hydrophosphination chemistry using diphenylphosphine under mild and benign reaction

  膦在合成化学中的重要性不可低估。催化加氢磷酸化提供了制备P-C键的理想方法，而无需苛刻的反应条件或化学计量的废物副产物。我们在此报告了我们在温和和良性反应条件（室温，无溶剂）下使用二苯膦在氢磷化化学中对两种生物相容的铁（III）配合物的研究，以及我们对苯膦进行氢磷化的扩展探索，可以将其调整为在不存在的情况下运行在热条件下进行单加氢磷化或在无溶剂的情况下使用铁（III）预催化剂生成双加氢磷化产物的催化剂。
• A Commercially Available Ruthenium Compound for Catalytic Hydrophosphination
  作者：Michael P. Cibuzar、Steven G. Dannenberg、Rory Waterman

  DOI：10.1002/ijch.201900070

  日期：2020.3

  available ruthenium compound, bis(cyclopentadienylruthenium dicarbonyl) dimer ([CpRu(CO)2]2), was explored. Styrene derivatives or Michael acceptors react readily with either primary or secondary phosphines in the presence of 0.1 mol % of [CpRu(CO)2]2 under photolysis with an inexpensive and commercially available UV/A 9 W lamp. In comparison to related photoactivated hydrophosphination reactions with [CpFe(CO)2]2

  探索了用市售钌化合物双（环戊二烯基钌二羰基）二聚体（[CpRu（CO）2 ] 2）进行的磷酸化。苯乙烯衍生物或迈克尔受体在0.1摩尔％[CpRu（CO）2 ] 2的存在下，可通过廉价和可商购的UV / A 9 W灯与伯或仲膦容易地反应。与以[CpFe（CO）2 ] 2为催化剂的相关光活化加氢磷酸化反应相比，这些钌催化的反应以相对较高的速率进行，且催化剂负载量较低。
• Hydrophosphination of alkenes and alkynes with primary phosphines catalyzed by zirconium complexes bearing aminophenolato ligands
  作者：Yu Zhang、Xinxin Wang、Yaorong Wang、Dan Yuan、Yingming Yao

  DOI：10.1039/c8dt02122h

  日期：——

  activity and chemo-selectivity in catalyzing intermolecular hydrophosphination of C–C multiple bonds with primary phosphines under mild conditions. A broad range of alkenes and alkynes underwent a mono-addition reaction with phenylphosphine, which generated secondary phosphines in 39–99% yields and >7 : 1 selectivity (over double hydrophosphination).

  由胺桥联的双（酚基）配体稳定的锆配合物在温和条件下，在催化带有主膦的CC多重键的分子间加氢磷酸化方面表现出良好的活性和化学选择性。广泛的烯烃和炔烃与苯基膦进行单加成反应，生成次膦的产率为39-99％，选择性大于7：1（双氢磷化处理）。
• Intermolecular Zirconium-Catalyzed Hydrophosphination of Alkenes and Dienes with Primary Phosphines
  作者：Michael B. Ghebreab、Christine A. Bange、Rory Waterman

  DOI：10.1021/ja503036z

  日期：2014.7.2

  Catalytic hydrophosphination of terminal alkenes and dienes with primary phosphines (RPH2; R = Cy, Ph) under mild conditions has been demonstrated using a zirconium complex, [kappa(5)-N,N,N,N,C-(Me3SiN-CH2CH2)(2)NCH2CH2NSiMe2CH]Zr (1). Exclusively anti-Markovnikov functionalized products were observed, and the catalysis is selective for either the secondary or tertiary phosphine (i.e., double hydrophosphination) products, depending on reaction conditions. The utility of the secondary phosphine products as substrates for further elaboration was demonstrated with a platinum-catalyzed asymmetric alkylation reaction.