diethyl (3-(4-methoxyphenyl)propyl)phosphonate | 1245751-07-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl (3-(4-methoxyphenyl)propyl)phosphonate
• 英文别名: diethyl 3-(4-methoxyphenyl)propyl-1-phosphonate；1-(3-Diethoxyphosphorylpropyl)-4-methoxybenzene；1-(3-diethoxyphosphorylpropyl)-4-methoxybenzene
• CAS: 1245751-07-8
• 化学式: C₁₄H₂₃O₄P
• 分子量: 286.308
• InChiKey: YVEGYLIRSVTOJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 potassium tert-butylate 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 以187.4 mg的产率得到diethyl (3-(4-methoxyphenyl)propyl)phosphonate
  参考文献：
  名称：

  Room-Temperature Alternative to the Arbuzov Reaction: The Reductive Deoxygenation of Acyl Phosphonates

  摘要：

  The reductive deoxygenation of acyl phosphonates using a Wolff-Kishner-like sequence is described. This transformation allows direct access to alkyl phosphonates from acyl phosphonates at room temperature. The method can be combined with acyl phosphonate synthesis into a one pot, four-step procedure for the conversion of carboxylic acids into alkyl phosphonates. The methodology works well for a variety of aliphatic acids and shows a functional group tolerance similar to that of other hydrazone-forming reactions.

  DOI：

  10.1021/ol1015493

文献信息

• Visible Light-Induced Selective Generation of Radicals from Organoborates by Photoredox Catalysis
  作者：Yusuke Yasu、Takashi Koike、Munetaka Akita

  DOI：10.1002/adsc.201200588

  日期：2012.12.14

  A new strategy for the generation of carbon-centered radicals via oxidation of alkyl-, allyl-, benzyl- and arylborates by visible-light-driven single electron transfer (SET) photoredox catalysis has been established. The generated radicals smoothly react with TEMPO and electron-deficient alkenes to afford CO and CC coupling products, respectively. In this radical initiating system, cyclic organo(triol)borates

  碳中心自由基的生成的新策略经由通过可见光驱动单电子转移（SET）photoredox催化烷基- ，烯丙基- ，苄基-氧化arylborates和已经建立。产生的自由基与TEMPO和缺电子的烯烃平稳反应，分别提供CO和CC偶联产物。在该自由基引发体系中，环状有机（三醇）硼酸酯被证明是有用的自由基前体。
• Facile access to functionalized chiral secondary benzylic boronic esters <i>via</i> catalytic asymmetric hydroboration
  作者：Suman Chakrabarty、Hector Palencia、Martha D. Morton、Ryan O. Carr、James M. Takacs

  DOI：10.1039/c8sc05613g

  日期：——

  the γ- or δ-position undergo rhodium-catalyzed asymmetric hydroboration by pinacolborane to give functionalized chiral secondary benzylic boronic esters in yields up to 86% and enantiomer ratios up to 99 : 1. Compared to minimally-functionalized terminal and 1,1-disubstituted vinyl arenes, there are relatively few reports of efficient catalytic asymmetric hydroboration (CAHB) of more highly functionalized

  在 γ- 或 δ- 位带有芳基或杂芳基取代基的烯丙基和高烯丙基膦酸酯通过频哪醇硼烷进行铑催化的不对称硼氢化，得到官能化的手性仲苄基硼酸酯，产率高达 86%，对映异构体比率高达 99:1。对于最小官能化末端和 1,1-二取代乙烯基芳烃，关于更高度官能化的内部烯烃的有效催化不对称硼氢化 (CAHB) 的报道相对较少。带有多种常见杂环系统的膦酸盐底物，包括呋喃、吲哚、吡咯和噻吩衍生物，以及带有碱性氮取代基（例如，吗啉和吡嗪）是可以耐受的，尽管位于烯烃附近的供体取代基会影响反应过程。立体异构体 ( E )- 和 ( Z )- 底物提供与硼酸化产物相同的主要对映异构体。氘标记研究表明，快速 ( Z )- 到 ( E )-烯烃异构化是CAHB 期间观察到的 ( E / Z )-立体收敛的原因。手性硼酸酯产品的合成效用通过立体定向 C-B 键转换来说明，包括立体保持性亲电试剂促进 1,2-B-to-C 迁移、立体反转
• Phosphonylation of alkyl radicals
  作者：Junyue Yin、Xinru Lin、Linxiang Chai、Cheng-Yu Wang、Lin Zhu、Chaozhong Li

  DOI：10.1016/j.chempr.2023.03.016

  日期：2023.7

  remains elusive. Herein, we report the decarboxylative radical phosphonylation with trialkyl phosphites. Thus with the co-catalysis of 4DPAIPN (1,2,3,5-tetrakis(diphenylamino)-4,6-dicyanobenzene) and Cu(OAc)2, the visible light-induced reaction of redox-active esters of aliphatic carboxylic acids with trialkyl phosphites at room temperature provides the corresponding alkylphosphonates in satisfactory

  烷基膦酸酯在药物、农用化学品和材料科学中有着广泛的应用，其合成在有机化学中至关重要。虽然亲核和亲电 C(sp 3 )-膦酰化已有充分记录，但烷基的膦酰化仍然难以捉摸。在此，我们报道了亚磷酸三烷基酯的脱羧自由基膦酰化反应。因此，在 4DPAIPN (1,2,3,5-四(二苯氨基)-4,6-二氰基苯) 和 Cu(OAc) 2的共催化下，在室温下，脂肪族羧酸的氧化还原活性酯与亚磷酸三烷基酯发生可见光诱导反应，以令人满意的产率提供相应的烷基膦酸酯。该方案具有广泛的底物范围和广泛的官能团兼容性，能够实现复杂分子的后期修饰。提出了一种涉及烷基与 P(OR) 3的铜辅助偶联，然后对所得鏻中间体进行 Arbuzov 型脱烷基化的机制。
• Room-Temperature Alternative to the Arbuzov Reaction: The Reductive Deoxygenation of Acyl Phosphonates
  作者：Sean M. A. Kedrowski、Dennis A. Dougherty

  DOI：10.1021/ol1015493

  日期：2010.9.17

  The reductive deoxygenation of acyl phosphonates using a Wolff-Kishner-like sequence is described. This transformation allows direct access to alkyl phosphonates from acyl phosphonates at room temperature. The method can be combined with acyl phosphonate synthesis into a one pot, four-step procedure for the conversion of carboxylic acids into alkyl phosphonates. The methodology works well for a variety of aliphatic acids and shows a functional group tolerance similar to that of other hydrazone-forming reactions.