Cyclohexanecarbonyl-phosphonic acid dimethyl ester | 1490-12-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: Cyclohexanecarbonyl-phosphonic acid dimethyl ester
• 英文别名: Dimethyl cyclohexanoylphosphonate；cyclohexyl(dimethoxyphosphoryl)methanone
• CAS: 1490-12-6
• 化学式: C₉H₁₇O₄P
• 分子量: 220.205
• InChiKey: VYANKHDEGZMIHL-UHFFFAOYSA-N

物化性质

• 沸点：
  90-93 °C(Press: 1 Torr)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Cyclohexanecarbonyl-phosphonic acid dimethyl ester 在 palladium on activated charcoal 氢气 、 铜 作用下， 以 乙醇 、 苯 为溶剂， 生成 dimethyl (cyclohexylmethyl)phosphonate
  参考文献：
  名称：

  Copper-catalyzed decomposition of some dimethylphosphono-substituted diazoalkanes

  摘要：

  DOI：

  10.1021/jo00800a026
• 作为产物：
  描述：

  三甲氧基磷 以80%的产率得到
  参考文献：
  名称：

  KOJIMA MITSUMASA; YAMASHITA MITSIJI; YOSHIDA HIROSHI; OGATA TSUYOSHI; INO+, SYNTHESIS, 1979, NO 2, 147-148

  摘要：

  DOI：

文献信息

• COMPOUNDS FOR THE INHIBITION OF INDOLEAMINE-2,3-DIOXYGENASE
  申请人：Merck Patent GmbH

  公开号：US20160075711A1

  公开（公告）日：2016-03-17

  The present invention relates to compounds, and pharmaceutically acceptable compositions thereof, useful as antagonists of IDO, and for the treatment of IDO-related disorders.

  本发明涉及化合物及其药学上可接受的组合物，用作IDO拮抗剂，用于治疗与IDO相关的疾病。
• New Synthesis and Hydroboration of Vinylphosphonates
  作者：Mitsuji Yamashita、Mitsumasa Kojima、Hiroshi Yoshida、Tsuyoshi Ogata、Saburo Inokawa

  DOI：10.1246/bcsj.53.1625

  日期：1980.6

  The Arbuzov reaction of trimethyl and triethyl phosphites with acyl chlorides gave 1-oxoalkylphosphonates in 57–80% yields. The Wittig reaction of the phosphonates with methylenetriphenylphosphorane gave vinylphosphonates in 25–59% yields. Hydroboration of vinylphosphonates in oxolane gave 2-hydroxyethylphosphonates in 50–65% yields. The procedure seems to be a good synthetic method to afford 1-alkyl-substituted

  亚磷酸三甲酯和三乙酯与酰氯的 Arbuzov 反应得到 1-氧代烷基膦酸酯，产率为 57-80%。膦酸酯与亚甲基三苯基膦的 Wittig 反应生成乙烯基膦酸酯，产率为 25-59%。乙烯基膦酸酯在氧杂环戊烷中的硼氢化反应得到 2-羟乙基膦酸酯，产率为 50-65%。该程序似乎是一种很好的合成方法，可以提供比起始的 1-氧代烷基膦酸酯多一个碳原子的 1-烷基取代的 2-羟乙基膦酸酯。
• Diametric Stereocontrol in Dynamic Catalytic Reduction of Racemic Acyl Phosphonates: Divergence from α-Keto Ester Congeners
  作者：Michael T. Corbett、Jeffrey S. Johnson

  DOI：10.1021/ja310980q

  日期：2013.1.16

  Ru-catalyzed asymmetric transfer hydrogenation of acyl phosphonates: reduction proceeded from the opposite face relative to that observed in the analogous reduction of α-keto esters. The first highly selective catalytic hydrogenation of acyl phosphonates was utilized in the dynamic kinetic resolution of α-aryl acyl phosphonates, providing β-stereogenic α-hydroxy phosphonic acid derivatives.

  在 Ru 催化的酰基膦酸酯的不对称转移氢化中观察到了意想不到的二分法：相对于在 α-酮酯的类似还原中观察到的相反面进行还原。酰基膦酸酯的第一次高选择性催化氢化用于 α-芳基酰基膦酸酯的动态动力学拆分，提供 β-立体异构 α-羟基膦酸衍生物。
• Reactions of acyl phosphonates with organoaluminum reagents: a new method for the synthesis of secondary and tertiary α-hydroxy phosphonates
  作者：Ozlem Seven、Sidika Polat-Cakir、Md. Shakhawoat Hossain、Mustafa Emrullahoglu、Ayhan S. Demir

  DOI：10.1016/j.tet.2011.03.036

  日期：2011.5

  ) with aryl and alkyl acyl phosphonates, which lead to the formation of α-hydroxy phosphonates in moderate to good yields, are reported. This method provides easy access to secondary and tertiary α-hydroxy phosphonates depending on the reaction conditions. The reactions of triethylaluminum with a series of acyl phosphonates at 0 °C gave the secondary α-hydroxy phosphonates, while at −100 °C they afford

  报道了有机铝试剂（三甲基铝，三乙基铝等）与芳基和烷基酰基膦酸酯的反应，导致以中等至良好的产率形成α-羟基膦酸酯。根据反应条件，该方法可轻松获得仲和叔α-羟基膦酸酯。三乙基铝与一系列酰基膦酸酯在0°C的反应生成仲α-羟基膦酸酯，而在-100°C时，它们生成叔α-羟基膦酸酯。
• Cyanide Ion Promoted Addition of Acylphosphonates to Diethyl Cyanophosphonate: Synthesis of Phosphonocyanohydrin O-Phosphates
  作者：Ayhan Demir、Asuman Aybey、Mustafa Emrullahoglu

  DOI：10.1055/s-0029-1216634

  日期：2009.5

  Cyanide ion catalyzed addition of acylphosphonates to diethyl cyanophosphonate furnished phosphonocyanohydrin O-phosphates in high yield. The reaction works via the phosphonate-phosphate rearrangement, followed by the addition of diethyl ­cyanophosphonate to the cyanohydrin phosphate anion. phosphonocyanohydrins - diethyl cyanophosphonate - addition reactions - acyl phosphonates - nucleophilic additions

  氰化物离子将酰基膦酸酯加成到氰基膦酸二乙酯中，可高产率地提供膦酰基氰醇O-磷酸酯。该反应通过膦酸酯-磷酸重排进行，然后将氰基膦酸二乙酯添加至氰醇磷酸酯阴离子中。 膦酰基氰醇-氰基膦酸二乙酯-加成反应-酰基膦酸酯-亲核加成