ethyl hydrogen ((4-chlorophenyl)ethynyl)phosphonate | 1415656-79-9

• 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: ethyl hydrogen ((4-chlorophenyl)ethynyl)phosphonate
• 英文别名: Ethyl hydrogen (4-chlorophenyl)ethynylphosphonate；2-(4-chlorophenyl)ethynyl-ethoxyphosphinic acid
• CAS: 1415656-79-9
• 化学式: C₁₀H₁₀ClO₃P
• 分子量: 244.614
• InChiKey: CULAMUXCIUZZQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl hydrogen ((4-chlorophenyl)ethynyl)phosphonate 在 (acetonitrile)[(2-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 30.0h， 生成 2-ethoxy-4-(4-chlorophenyl)-6-(3-phenylpropyl)-1,2-oxaphosphorin 2-oxide
  参考文献：
  名称：

  Gold-Catalyzed Sequential Alkyne Activation for the Synthesis of 4,6-Disubstituted Phosphorus 2-Pyrones

  摘要：

  Tandem gold-catalyzed addition of alkynyl phosphonic acid monoethyl esters to terminal alkynes and cyclization were developed for the synthesis of 4,6-disubstituted phosphorus 2-pyrones in one reaction vessel based on the concept of sequential alkyne activation. Alkynyl enol phosphonates were selectively obtained through the gold-catalyzed addition reaction in the presence of a catalytic amount of triethylamine. Also, gold-catalyzed cyclization of alkynyl enol phosphonates was successful in giving a variety of 4,6-disubstituted phosphorus 2-pyrones.

  DOI：

  10.1021/ol3029274
• 作为产物：
  描述：

  4-氯苯乙炔 在 N-溴代丁二酰亚胺(NBS) 、 水 、 silver nitrate 、 sodium hydroxide 作用下， 以 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 26.0h， 生成 ethyl hydrogen ((4-chlorophenyl)ethynyl)phosphonate
  参考文献：
  名称：

  (苯乙炔基)膦酸乙酯与芳烃环化偶联合成磷色酮

  摘要：

  据报道，通过将芳炔插入 P-O 键来合成磷化色酮的一种简单而有效的策略。这一操作简单的反应与不同的官能团相容，通过一步同时形成 C-P 和 C-O 键来提供各种磷色酮，产率中等至良好，涉及磷原子的 Fries 重排是该反应的关键步骤。

  DOI：

  10.1021/acs.orglett.3c01938

文献信息

• NOVEL PHOSPHORUS 2-PYRONE DERIVATIVE AND PREPARATION METHOD THEREOF
  申请人：KNU-INDUSTRY COOPERATION FOUNDATION

  公开号：US20150191497A1

  公开（公告）日：2015-07-09

  Provided are a novel phosphorus 2-pyrone derivative and a preparation method thereof. The phosphorus 2-pyrone derivative according to the present invention is capable of being efficiently synthesized by treating an alkyl hydrogen alkynylphosphonate derivative and an alkyne derivative with a minimal amount of a gold catalyst.

  本发明提供了一种新型的磷2-吡喃衍生物及其制备方法。根据本发明，所述磷2-吡喃衍生物能够通过用少量金催化剂处理烷基氢基炔基磷酸酯衍生物和炔烃衍生物来高效合成。
• Phosphorus 2-pyrone derivative and preparation method thereof
  申请人：KNU-INDUSTRY COOPERATION FOUNDATION

  公开号：US09200019B2

  公开（公告）日：2015-12-01

  Provided are a novel phosphorus 2-pyrone derivative and a preparation method thereof. The phosphorus 2-pyrone derivative according to the present invention is capable of being efficiently synthesized by treating an alkyl hydrogen alkynylphosphonate derivative and an alkyne derivative with a minimal amount of a gold catalyst.

  本发明提供了一种新颖的磷2-吡喃衍生物及其制备方法。根据本发明，可以通过使用最少量的金催化剂处理烷基氢炔基膦酸酯衍生物和烷基炔衍生物来高效合成磷2-吡喃衍生物。
• Gold-Catalyzed Sequential Alkyne Activation for the Synthesis of 4,6-Disubstituted Phosphorus 2-Pyrones
  作者：Juntae Mo、Dongjin Kang、Dahan Eom、Sung Hong Kim、Phil Ho Lee

  DOI：10.1021/ol3029274

  日期：2013.1.4

  Tandem gold-catalyzed addition of alkynyl phosphonic acid monoethyl esters to terminal alkynes and cyclization were developed for the synthesis of 4,6-disubstituted phosphorus 2-pyrones in one reaction vessel based on the concept of sequential alkyne activation. Alkynyl enol phosphonates were selectively obtained through the gold-catalyzed addition reaction in the presence of a catalytic amount of triethylamine. Also, gold-catalyzed cyclization of alkynyl enol phosphonates was successful in giving a variety of 4,6-disubstituted phosphorus 2-pyrones.
• Synthesis of Phosphachromones by Cyclized Coupling of Ethyl Hydrogen (Phenylethynyl)phosphonate with Arynes
  作者：Yu Guo、Jianke Su、Jian Xu、Qiuling Song

  DOI：10.1021/acs.orglett.3c01938

  日期：2023.9.8

  been reported via the insertion of arynes into P–O bonds. This operationally simple reaction is compatible with different functional groups, affording various phosphachromones by the simultaneous formation of C–P and C–O bonds in one step with moderate to good yields, and the Fries rearrangement involving phosphorus atoms is a key step in the reaction.

  据报道，通过将芳炔插入 P-O 键来合成磷化色酮的一种简单而有效的策略。这一操作简单的反应与不同的官能团相容，通过一步同时形成 C-P 和 C-O 键来提供各种磷色酮，产率中等至良好，涉及磷原子的 Fries 重排是该反应的关键步骤。

表征谱图