diethyl (1-(2-methoxyphenyl)vinyl)phosphonate | 1159205-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl (1-(2-methoxyphenyl)vinyl)phosphonate
• 英文别名: 1-(1-Diethoxyphosphorylethenyl)-2-methoxybenzene；1-(1-diethoxyphosphorylethenyl)-2-methoxybenzene
• CAS: 1159205-33-0
• 化学式: C₁₃H₁₉O₄P
• 分子量: 270.265
• InChiKey: CAQLVHALVOGUSY-UHFFFAOYSA-N

物化性质

• 沸点：
  379.8±34.0 °C(predicted)
• 密度：
  1.100±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (1-(2-methoxyphenyl)vinyl)phosphonate 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 C₄₃H₃₆F₆FeNP₂ 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、1.0 MPa 条件下， 反应 24.0h， 以98%的产率得到1-(2-methoxyphenyl)ethylphosphonic acid diethyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Chiral α-Aryl or α-Alkyl Substituted Ethylphosphonates via Rh-Catalyzed Asymmetric Hydrogenation with a P-Stereogenic BoPhoz-Type Ligand

  摘要：

  An enantioselective synthesis of optically active 1-aryl or 1-alkyl substituted ethylphosphonates, based on the first Rh-catalyzed asymmetric hydrogenation of corresponding alpha,beta-unsaturated precursors with a P-stereogenic BoPhoz-type ligand under the mild condition, was developed, in which a wide range of 1-aryl or 1-alkyl substituted ethylphosphonates were achieved in up to 98% ee.

  DOI：

  10.1021/jo900417m
• 作为产物：
  描述：

  乙酰亚磷酸二乙酯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 caesium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 diethyl (1-(2-methoxyphenyl)vinyl)phosphonate
  参考文献：
  名称：

  α-膦酰基乙烯基芳基磺酸盐：通过钯催化的铃木反应合成α-取代的乙烯基膦酸盐的有吸引力的伙伴

  摘要：

  通过铃木反应合成α-取代的乙烯基膦酸酯的新的，有吸引力的偶联伙伴已被开发出来。发达的以O为中心的亲电试剂与各种有机硼试剂偶合，以中等至极好的收率得到α-取代的乙烯基膦酸酯。该协议具有广泛的基板范围，温和的条件和高效率。

  DOI：

  10.1002/ejoc.201600056

文献信息

• A Simple and Efficient Method for One-Pot, Three-Component Synthesis of Terminal Vinylphosphonates Using a Task-Specific Ionic Liquid
  作者：Sara Sobhani、Moones Honarmand

  DOI：10.1055/s-0032-1317965

  日期：——

  convenient and practical method for the one-pot, three-component synthesis of terminal vinylphosphonates from readily available starting materials (aryl/alkyl/heteroaryl aldehydes, nitromethane and trialkylphosphites) through a tandem Henry–­Michael reaction followed by nitro elimination in the presence of 5-hydroxypentylammonium acetate (5-HPAA) as a task-specific ionic liquid, is described. This method offers

  一种方便实用的方法，用于从易得的起始材料（芳基/烷基/杂芳基醛、硝基甲烷和亚磷酸三烷基酯）通过串联亨利-迈克尔反应，然后在存在下硝基消除的情况下，一锅三组分合成末端乙烯基膦酸酯描述了作为特定任务的离子液体的 5-羟基戊基乙酸铵 (5-HPAA)。这种方法提供了几个优点，例如使用可重复使用且价格低廉的离子液体，这是一种环境友好的反应介质，以及不需要专门设备的简单反应设置。该方法在温和的反应条件下提供了良好的产物收率。
• A Palladium-Catalyzed Decarboxylative Heck-Type Reaction of Disubstituted Vinylphosphonates in the Stereoselective Synthesis of Trisubstituted Vinylphosphonates
  作者：Linjing Ren、Maogang Ran、Jiaxin He、Dan Xiang、Feng Chen、Peijun Liu、Chunyang He、Qiuli Yao

  DOI：10.1002/ejoc.201900810

  日期：2019.9.8

  We describe a highly stereoselective and atomically economical approach for the preparation of trisubstituted vinylphosphonates through palladium‐catalyzed decarboxylative Heck‐type reactions of vinylphosphonates. Excellent E/Z selectivity was achieved mostly with E‐isomers with oxygen in the air was the sole oxidant; this was difficult to achieve via traditional methods. This work is the first example

  我们描述了一种通过钯催化的乙烯基膦酸酯的脱羧Heck型反应制备三取代乙烯基膦酸酯的高度立体选择性和原子经济的方法。大多数E异构体均具有出色的E / Z选择性，其中空气中的氧气是唯一的氧化剂。通过传统方法很难做到这一点。这项工作是通过催化的脱羧Heck型反应合成乙烯基膦酸酯的第一个实例。
• Applications of α-Phosphonovinyl Tosylates in the Synthesis of α-Arylethenylphosphonates via Suzuki–Miyaura Cross-Coupling Reactions
  作者：Yewen Fang、Li Zhang、Jinjian Li、Xiaoping Jin、Meijuan Yuan、Ruifeng Li、Rong Wu、Jianghua Fang

  DOI：10.1021/ol503518h

  日期：2015.2.20

  It has been demonstrated for the first time that alpha-phosphonovinyl tosylates could efficiently couple with a range of arylboronic acids to access alpha-arylethenylphosphonates. The unprecedented procedure exhibits excellent functional group tolerance, giving the terminal vinylphosphonates in good to excellent isolated yields (60-99%) under mild reaction conditions.
• α-Phosphonovinyl Arylsulfonates: An Attractive Partner for the Synthesis of α-Substituted Vinylphosphonates through Palladium-Catalyzed Suzuki Reactions
  作者：Yewen Fang、Li Zhang、Xiaoping Jin、Jinjian Li、Meijuan Yuan、Ruifeng Li、Tong Wang、Tao Wang、Hanjun Hu、Juejun Gu

  DOI：10.1002/ejoc.201600056

  日期：2016.3

  A new and attractive coupling partner for the synthesis of α‐substituted vinylphosphonates through Suzuki reactions has been developed. The developed O‐centered electrophiles couple with various organoboron reagents to give α‐substituted vinylphosphonates in moderate to excellent yields. This protocol features broad substrate scope, mild conditions, and high efficiency.

  通过铃木反应合成α-取代的乙烯基膦酸酯的新的，有吸引力的偶联伙伴已被开发出来。发达的以O为中心的亲电试剂与各种有机硼试剂偶合，以中等至极好的收率得到α-取代的乙烯基膦酸酯。该协议具有广泛的基板范围，温和的条件和高效率。
• Enantioselective Synthesis of Chiral α-Aryl or α-Alkyl Substituted Ethylphosphonates via Rh-Catalyzed Asymmetric Hydrogenation with a <i>P</i>-Stereogenic BoPhoz-Type Ligand
  作者：Dao-Yong Wang、Xiang-Ping Hu、Jun Deng、Sai-Bo Yu、Zheng-Chao Duan、Zhuo Zheng

  DOI：10.1021/jo900417m

  日期：2009.6.5

  An enantioselective synthesis of optically active 1-aryl or 1-alkyl substituted ethylphosphonates, based on the first Rh-catalyzed asymmetric hydrogenation of corresponding alpha,beta-unsaturated precursors with a P-stereogenic BoPhoz-type ligand under the mild condition, was developed, in which a wide range of 1-aryl or 1-alkyl substituted ethylphosphonates were achieved in up to 98% ee.