dimethyl (3-oxobutyl)phosphonate | 20335-89-1

• 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: dimethyl (3-oxobutyl)phosphonate
• 英文别名: dimethyl-(3-oxobutyl)phosphonate；Dimethyl-(2-acetylethyl)-phosphonat；4-Dimethoxyphosphorylbutan-2-one
• CAS: 20335-89-1
• 化学式: C₆H₁₃O₄P
• 分子量: 180.141
• InChiKey: LZBAEUMIRMAMFM-UHFFFAOYSA-N

物化性质

• 沸点：
  103-104 °C(Press: 0.8 Torr)
• 密度：
  1.1707 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  dimethyl (3-oxobutyl)phosphonate 在 溴 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 (4-Bromo-3-oxo-butyl)-phosphonic acid dimethyl ester 、 (2-Bromo-3-oxo-butyl)-phosphonic acid dimethyl ester
  参考文献：
  名称：

  酮的选择性溴化。5-氨基乙酰丙酸的简便合成

  摘要：

  摘要 不对称酮与 Br2 在甲醇中的溴化反应在较少取代的甲基碳上以良好的产率区域选择性地进行。使用这种方法溴化乙酰丙酸，然后进行叠氮化和胺化，以 36% 的总产率高效地三步合成 5-氨基乙酰丙酸。

  DOI：

  10.1080/00397919408010567
• 作为产物：
  描述：

  二甲基-乙烯基磷酸酯 、 乙醛 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以68%的产率得到dimethyl (3-oxobutyl)phosphonate
  参考文献：
  名称：

  Metal-free, hydroacylation of CC and NN bonds via aerobic C–H activation of aldehydes, and reaction of the products thereof

  摘要：

  在本报告中，我们详细评估了使用需氧起始、不含金属的氢酰化方法，将多种CC和NN受体分子与广泛范围的醛进行反应的情况。我们所开发的有氧活化条件与之前的氢酰化条件形成鲜明对比，后者倾向于使用过渡金属、需要热或光化学分解的过氧化物，或者N-杂环卡宾。这些温和的条件使得许多涉及敏感反应物的反应得以进行，或许最为重要的是，能够让α-功能化的手性醛在基于自由基的氢酰化反应中完全保持光学纯度。我们还展示了所得氢酰化产物如何转化成其他有用的中间体，例如γ-酮-磺酰胺、磺内酰胺、磺内酯、环状N-磺酰亚胺和酰胺。

  DOI：

  10.1039/c3ob41632a

文献信息

• Me 3 P-catalyzed addition of hydrogen phosphoryl compounds P(O)H to electron-deficient alkenes: 1 to 1 vs 1 to 2 adducts
  作者：Tian-Zeng Huang、Tieqiao Chen、Yuta Saga、Li-Biao Han

  DOI：10.1016/j.tet.2017.10.070

  日期：2017.12

  Trimethyl phosphine was used as an efficient catalyst for the addition of P(O)-H compounds to electron-deficient alkenes. The addition reactions were generally conducted using a catalytic amount of Me3P under mild reaction conditions. Both 1 to 1 and 1 to 2 adducts were obtained.

  三甲基膦被用作将P（O）-H化合物加成至缺电子烯烃的有效催化剂。通常在温和的反应条件下使用催化量的Me 3 P进行加成反应。获得了1对1和1对2个加合物。
• NON-AQUEOUS ELECTROLYTE AND ELECTRICITY STORAGE DEVICE
  申请人：UBE INDUSTRIES, LTD.

  公开号：US20150372349A1

  公开（公告）日：2015-12-24

  The present invention provides a nonaqueous electrolytic solution capable of improving electrochemical characteristics in the case of using an energy storage device at a high temperature and further capable of inhibiting the gas generation as well as a capacity retention rate after a high-temperature cycle, and also to provide an energy storage device using the same. Disclosed are a nonaqueous electrolytic solution having an electrolyte salt dissolved in a nonaqueous solvent, the nonaqueous electrolytic solution containing a phenyl ester compound represented by the following general formula (I), and an energy storage device. (In the formula, R f represents a fluoroalkyl group having 1 to 6 carbon atoms; X represents a halogen atom; each of p and q is an integer of 1 to 4; and (p+q) is 5 or less. A has a structure represented by —S(═O) 2 —, —C(═O)—, —C(═O)—O—, —C(═O)-L 1 -C(═O)—, —C(═O)-L 2 -P(═O)(OR)—O—, or —P(═O)(OR)—O—. Y represents a fluorine atom, a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group; L 1 represents an alkylene group, an alkenylene group, an alkynylene group, or a direct bond; L 2 represents an alkylene group; and R represents an alkyl group. However, only when A is —S(═O) 2 —, Y may be a fluorine atom; and only when A is —C(═O)—, Y may be a hydrogen atom. At least one hydrogen atom in each group of the aforementioned alkyl group, alkenyl group, alkynyl group, aryl group, alkylene group, alkenylene group, and alkynylene group may be substituted with a halogen atom.)

  本发明提供了一种非水电解质溶液，能够在高温下使用能量存储装置时改善电化学特性，并且在高温循环后能够抑制气体生成以及保持容量保留率，还提供了使用该非水电解质溶液的能量存储装置。所述非水电解质溶液包含溶解在非水溶剂中的电解质盐，该非水电解质溶液包含下述通式（I）所代表的苯酯化合物，以及能量存储装置。（在该式中，Rf代表具有1至6个碳原子的氟烷基；X代表卤素原子；p和q中的每一个是1至4的整数；以及（p+q）不超过5。A具有由—S(═O)2—、—C(═O)—、—C(═O)—O—、—C(═O)-L1-C(═O)—、—C(═O)-L2-P(═O)(OR)—O—或—P(═O)(OR)—O—表示的结构。Y代表氟原子、氢原子、烷基、烯基、炔基或芳基；L1代表烷基、烯基、炔基或直链键；L2代表烷基；R代表烷基。但是，仅当A为—S(═O)2—时，Y可以是氟原子；仅当A为—C(═O)—时，Y可以是氢原子。上述烷基、烯基、炔基、芳基、烷基、烯基和炔基中的每一组中至少一个氢原子可以被卤素原子取代。）
• A study on the michael addition of dialkylphosphites to methylvinylketone
  作者：György Keglevich、Melinda Sipos、Daniella Takács、István Greiner

  DOI：10.1002/hc.20266

  日期：2007.4

  The addition of dialkylphosphites to methylvinylketone giving dialkyl-3-oxobutylphos- phonates was studied applying different reagents, such as NaOR/ROH, NaOH/H2O under PTC, DBU, and R3Al (R = Me, Et) under different conditions to find the optimum choice regarding efficiency and selectivity. Possible extensions to a few other model compounds were also investigated. © 2007 Wiley Periodicals, Inc. Heteroatom

  使用不同的试剂，如 NaOR/ROH、NaOH/H2O 在 PTC、DBU 和 R3Al（R = Me、Et）下，在不同条件下研究了将二烷基亚磷酸酯添加到甲基乙烯基酮中得到二烷基-3-氧代丁基膦酸酯以找到最佳关于效率和选择性的选择。还研究了一些其他模型化合物的可能扩展。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:226–229, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20266
• Appleton, Diana; Duguid, A. Bruce; Lee, Sung-Koo, Journal of the Chemical Society. Perkin transactions I, 1998, # 1, p. 89 - 102
  作者：Appleton, Diana、Duguid, A. Bruce、Lee, Sung-Koo、Ha, Young-Jin、Ha, Hyun-Joon、Leeper, Finian J.

  DOI：——

  日期：——
• Zinc-Mediated Chain Extension of β-Keto Phosphonates
  作者：Christopher A. Verbicky、Charles K. Zercher

  DOI：10.1021/jo000343f

  日期：2000.9.1

  A variety of beta-keto phosphonates can be converted to gamma-keto phosphonates through reaction with ethyl(iodomethyl)zinc. The presence of alpha-alkyl substituents, Lewis basic functionality, and modestly acidic NH-protons are accommodated in substrates of this reaction. Chain extension of beta-keto phosphonates that contained olefinic functionality proceeded more quickly than cyclopropanation; however, it was not possible to effect the chain extension to the exclusion of cyclopropane formation. A primary reason for this imperfect chemoselectivity appears to be the slow chain extension of beta-keto phosphonates. Nevertheless, the simplicity, the scope, and efficiency of this method serve to make it an attractive alternative to the established methods for gamma-keto phosphonate formation.