Cyclohexyl-phosphonic acid diethyl ester | 7413-09-4

• 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: Cyclohexyl-phosphonic acid diethyl ester
• 英文别名: diethyl cyclohexylphosphonate；diethoxyphosphorylcyclohexane
• CAS: 7413-09-4
• 化学式: C₁₀H₂₁O₃P
• 分子量: 220.249
• InChiKey: CBAJXOXPGBXGDX-UHFFFAOYSA-N

物化性质

• 沸点：
  148 °C(Press: 1.5 Torr)
• 密度：
  1.032 g/cm3(Temp: 18 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 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：

  Cyclohexyl-phosphonic acid diethyl ester 在 五氯化磷 作用下， 生成 cyclohexyl-phosphonic acid ethyl ester-(4-nitro-phenyl ester)
  参考文献：
  名称：

  The Effect of Structure on the Reactivity of Alkylphosphonate Esters^1,2

  摘要：

  DOI：

  10.1021/ja01511a025
• 作为产物：
  描述：

  氯代环己烷 在 三氯化铝 、 三氯化磷 作用下， 生成 Cyclohexyl-phosphonic acid diethyl ester
  参考文献：
  名称：

  Organic Phosphorus Compounds. I. The Conversion of the Chloroaluminate Complexes, [RPCl₃][AlCl₄], to Alkyl Alkylphosphonochloridates and Dialkyl Alkylphosphonates

  摘要：

  DOI：

  10.1021/ja01570a072

文献信息

• Denitrohydrogenation of aliphatic nitro compounds and a new use of aliphatic nitro compounds as radical precursors
  作者：Noboru Ono、Hideyoshi Miyake、Akio Kamimura、Isami Hamamoto、Rui Tamura、Aritsune Kaji

  DOI：10.1016/s0040-4020(01)97180-7

  日期：1985.1

  Aliphatic nitro groups are replaced by hydrogen on treatment with tributyltin hydride which proceeds via free radical chain processes. As the nitro group is selectively denitrated and other reducible groups are not affected with tributyltin hydride, this reaction can be used as a method for removing the nitro group from polyfunctional compounds. The radical intermediates generated via denitration can

  在氢化三丁基锡氢化物处理中，脂肪族硝基被氢取代，氢化三丁基锡通过自由基链过程进行。由于硝基被选择性地反硝化并且其他可还原基团不受氢化三丁基锡的影响，因此该反应可用作从多官能化合物中去除硝基的方法。通过脱硝产生的自由基中间体也可用于碳-碳键形成反应。
• Simvastatin-Associated Memory Loss
  作者：Amanda Orsi、Olga Sherman、Zegga Woldeselassie

  DOI：10.1592/phco.21.7.767.34577

  日期：2001.6

  The statins are widely used to treat dyslipidemias. They are generally associated with mild adverse effects, but rarely, more serious reactions may occur. A 51-year-old man experienced delayed-onset, progressive memory loss while receiving simvastatin for hypercholesterolemia. His therapy was switched to pravastatin, and memory loss resolved gradually over the next month, with no recurrence of the adverse effect.

  他汀类药物广泛用于治疗脂代谢异常。一般而言，它们的副作用较轻，但偶尔也可能出现更严重的反应。一名51岁男性在接受辛伐他汀治疗高胆固醇血症期间，经历了延迟出现的进行性记忆丧失。治疗被更换为普伐他汀，记忆丧失在接下来的一个月内逐渐缓解，并且没有再出现副作用。
• The catalytic aerobic synthesis of quaternary α-hydroxy phosphonates via direct hydroxylation of phosphonate compounds
  作者：Lijun Gu、Cheng Jin、Hongtao Zhang

  DOI：10.1039/c4nj02072c

  日期：——

  A highly efficient Cu-catalyzed direct hydroxylation of phosphonate compounds has been developed. This transformation provides a powerful method for the synthesis of quaternary α-hydroxy phosphonates in good yields. The direct transformation process, regiospecific selectivity, and good tolerance to a variety of substituents make it an alternative approach to the reported protocols.

  已经开发了高效的铜催化的膦酸酯化合物的直接羟基化。该转化为以高收率合成α-羟基膦酸酯季盐提供了一种有力的方法。直接转化过程，区域特异性选择性以及对各种取代基的良好耐受性使其成为所报道方案的替代方法。
• Synthesis of Quaternary<i>α</i>-Hydroxy Phosphonates<i>via</i>Direct Hydroxylation of Phosphonate Compounds
  作者：Jiyan Liu、Wei Wang、Rui Wang、Lijun Gu

  DOI：10.1002/cjoc.201400858

  日期：2015.5

  It was found for the first time that Cs2CO3 serves as highly efficient catalyst for the direct hydroxylation reactions of phosphonates under mild conditions. This reaction provides an efficient approach to quaternary α‐hydroxy phosphonates, which possess intriguing biological activities and are widely used in many areas.

  首次发现在温和条件下，Cs 2 CO 3可以用作膦酸酯直接羟基化反应的高效催化剂。该反应提供了一种有效的方法来处理季铵化的α-羟基膦酸酯，其具有令人着迷的生物学活性，并在许多领域得到了广泛的应用。
• 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。