O,O-diisopropyl cyclohexylphosphonate | 7351-26-0

• 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: O,O-diisopropyl cyclohexylphosphonate
• 英文别名: diisopropyl cyclohexylphosphonate；Cyclohexylphosphonsaeurediisopropylester；Phosphonic acid, cyclohexyl-, bis(1-methylethyl) ester；di(propan-2-yloxy)phosphorylcyclohexane
• CAS: 7351-26-0
• 化学式: C₁₂H₂₅O₃P
• 分子量: 248.302
• InChiKey: CEBKCTBCWCLAST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O,O-diisopropyl cyclohexylphosphonate 在 正丁基锂 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 4.5h， 生成 (1-Azido-cyclohexyl)-phosphonic acid diisopropyl ester
  参考文献：
  名称：

  A New and Efficient Synthesis of α-Amino Cycloalkyl-Phosphonic AcidsviaElectrophilic Azidation of Cycloalkylphosphonates

  摘要：

  alpha-Amino cyclobutyl-, cyclopentyl- and cyclohexylphosphonic acids (13) were efficiently prepared from the related unsubstituted cycloalkphosphonates (5), in three steps including electrophilic azidation of the corresponding lithiated carbanions, hydrogenation of the intermediate alpha-azido cycloalkyl-phosphonates (10) and acidic hydrolysis of the resulting alpha-amino cycloalkyl-phosphonates (12).

  DOI：

  10.1080/00397919608004650
• 作为产物：
  描述：

  三异丙基亚磷酸酯 在 乙醇 、 镍 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 O,O-diisopropyl cyclohexylphosphonate
  参考文献：
  名称：

  Syntheses of [(1-alkylthio)]- and (1-mercapto)cycloalkane phosphonic esters by the reactions of cycloalkanethiones with trialkyl phosphites

  摘要：

  DOI：

  10.1021/jo00404a029

文献信息

• Hydrolyse Basique de phosphonates I. Étude qualitative
  作者：Henri Christol、Michel̀e Levy、Claude Marty

  DOI：10.1016/s0022-328x(00)88699-4

  日期：1968.6

  The hydrolysis of phosphonates by alkali in aqueous dioxane has been studied. The symmetrical phosphonates are hydrolysed with loss of one ester group to form a monoacid. With the mixed phosphonates the better leaving group is replaced.

  已经研究了在二恶烷水溶液中碱将膦酸酯水解的方法。对称的膦酸酯水解而失去一个酯基，形成一元酸。用混合的膦酸酯，更好的离去基团被取代。
• Facile Solid‐Phase Synthesis of Cycloalkylphosphonates and 1‐Cycloalkenylphosphonates Using Polymer‐Supported Phenylsulfonylmethylphosphonates
  作者：Xiao‐Ling Liu、Shou‐Ri Sheng、Wei Zhou、Qin‐Ying Wang、Xiao‐Lan Zhang、Bin Gong

  DOI：10.1080/00397910600978515

  日期：2007.1.1

  Abstract A facile procedure for the solid‐phase synthesis of cycloalkylphosphonates and 1‐cycloalkenylphosphonates in good yields and high purities using polystyrene‐supported phenylsulfonylmethylphosphonates with traceless sulfone linker strategy is described.

  摘要描述了使用聚苯乙烯负载的苯磺酰基甲基膦酸酯和无痕砜连接剂策略以良好的收率和高纯度固相合成环烷基膦酸酯和 1-环烯基膦酸酯的简便方法。
• A Practical Synthesis of Cycloalkylphosphonates from Trichloromethylphosphonates
  作者：Catherine Grandin、Noël Collignon、Philippe Savignac

  DOI：10.1055/s-1995-4427

  日期：1995.3

  Cycloalkylphosphonates 5 with ring size varying from 4 to 6 were synthesized in good overall yields, in two steps from trichloromethylphosphonates and ω-dibromoalkanes, via the corresponding α-trimethylsilyl cycloalkylphosphonates 4.

  通过相应的δ-三甲基硅基环烷基膦酸盐 4，以三氯甲基膦酸盐和Ï-二溴烷烃为原料，分两步合成了环径为 4 至 6 的环烷基膦酸盐 5，总产率良好。
• One-pot and efficient electrosynthesis of cycloalkylphosphonates from diisopropyl trichloromethylphosphonate using magnesium electrochemical activation
  作者：Philippe Jubault、Christian Feasson、Noël Collignon

  DOI：10.1016/0040-4039(96)00597-7

  日期：1996.5

  Various diisopropyl cycloalkylphosphonates were easily prepared in an one-pot sequence under mild conditions, by electrolysing diisopropyl trichloromethylphosphonate in the presence of ω,ω-dibromoalkanes. The use of an electrochemical activated magnesium amode significantly improved the rate and the yield of the two first steps of the reaction.

  通过在ω，ω-二溴代烷烃的存在下电解二异丙基三氯甲基膦酸酯，可以在温和条件下以一锅法轻松制备各种二异丙基环烷基膦酸酯。使用电化学活化的镁无定形显着提高了反应的两个第一步的速率和产率。
• ——
  作者：A. I. Kuramshin、E. S. Kuramshina、R. A. Cherkasov

  DOI：10.1023/a:1012352900754

  日期：——

  Depending on the reactant ratio and order of their mixing, reactions of dialkyl hydrogen phosphite with alkenes in the presence of catalytic amounts of homoligand carbonyl complexes of iron or chromium subgroup metals yield phosphonates by two pathways: reaction of dialkyl hydrogen phosphite with pi -coordinated alkene and addition to alkene of the product of reaction of dialkyl hydrogen phosphite with the transition metal carbonyl. The products of reactions of Fe(CO)(5) and W(CO)(6) with dialkyl hydrogen phosphites contain the phosphorus-metal bond.