1-二乙氧基磷酰-1-硝基-丙烷 | 6329-58-4

• 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
• 中文名称: 1-二乙氧基磷酰-1-硝基-丙烷
• 英文名称: Diethyl 1-nitropropanephosphonate
• 英文别名: Diaethyl-(1-nitropropyl)-phosphonat；diethyl 1-nitropropylphosphonate；(1-nitro-propyl)-phosphonic acid diethyl ester；Diethyl(1-nitropropyl)phosphonate；1-diethoxyphosphoryl-1-nitropropane
• CAS: 6329-58-4
• 化学式: C₇H₁₆NO₅P
• 分子量: 225.181
• InChiKey: UCVFMTDYGKKVPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  1-二乙氧基磷酰-1-硝基-丙烷 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以83%的产率得到
  参考文献：
  名称：

  Franklin, Synlett, 2000, # 8, p. 1154 - 1156

  摘要：

  DOI：
• 作为产物：
  描述：

  E,Z-Diethyl α-hydroxyiminopropylphosphonate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 1-二乙氧基磷酰-1-硝基-丙烷
  参考文献：
  名称：

  Enantioselective Synthesis of Quaternary α-Aminophosphonates via Conjugate Addition of α-Nitrophosphonates to Enones

  摘要：

  Enantioselective Michael addition of alpha-nitrophosphonates to enones for the synthesis of alpha-aminophosphonates is reported for the first time. The reaction proceeds in good to high yields and moderate to high selectivity in the presence of a new quinine thiourea catalyst. The quaternary nitrophosphonates were conveniently transformed to cyclic quaternary alpha-aminophosphonates via in situ reduction intramolecular cyclization or Baeyer-Villiger oxidation followed by in situ reduction intramolecular cyclization.

  DOI：

  10.1021/ol203132h

文献信息

• One-step Synthesis of Stabilized Phosphonates
  作者：Ali A. Kandil、Terence M. Porter、Keith N. Slessor

  DOI：10.1055/s-1987-27968

  日期：——

  Phosphonates possessing α-electron withdrawing functionalities can be readily prepared by treatment of nitriles, nitroalkanes, and esters with 2 molar equivalents of base followed by phosphonylation with diethyl chlorophosphate.

  具有α-吸电子官能团的膦酸盐可以通过将腈、硝基烷烃和酯与2摩尔当量的碱处理，随后与二乙基氯膦酸酯进行膦酰化来方便制备。
• A New Method for the Preparation of Conjugated Nitro Olefins
  作者：Masayuki Fujii

  DOI：10.1246/cl.1992.933

  日期：1992.6

  Condensation of 1-nitroalkanephosphonates with carbonyl compounds affords a new and facile method for the preparation of conjugated nitro olefins.

  1-硝基链烷膦酸酯与羰基化合物的缩合提供了一种新的、简便的制备共轭硝基烯烃的方法。
• Enantioselective Synthesis of α-Amino-γ-sulfonyl Phosphonates with a Tetrasubstituted Chiral α-Carbon<i>via</i>Quinine-Squaramide-Catalyzed Michael Addition of Nitrophosphonates to Vinyl Sulfones
  作者：Kalisankar Bera、Irishi N. N. Namboothiri

  DOI：10.1002/adsc.201300224

  日期：2013.5.3

  α‐Nitro‐γ‐sulfonyl phosphonates with a key tetrasubstituted chiral α‐carbon center have been synthesized for the first time in high yield and enantioselectivity through a quinine‐squaramide‐catalyzed conjugate addition of α‐nitro phosphonates to aryl vinyl sulfones. Representative examples presented here for the transformation of nitrosulfonyl phosphonates to aminosulfonyl phosphonates, alkylation

  具有关键的四取代手性α-碳中心的α-硝基-γ-磺酰基膦酸酯是通过奎宁-方酰胺催化的α-硝基膦酸酯向芳基乙烯基砜的共轭加成反应首次以高收率和对映选择性合成的。这里介绍的有关将硝基磺酰基膦酸酯转化为氨基磺酰基膦酸酯，在磺酰基基团的α位进行烷基化，然后进行脱磺化和扩大共轭物添加量的典型实例突出了该方法的实际应用。
• Highly Enantioselective Michael Addition of α-Substituted Nitrophosphonates to a Vinyl Sulfone
  作者：Yixin Lu、Guo-Ying Chen

  DOI：10.1055/s-0033-1338434

  日期：——

  Organocatalytic asymmetric Michael reaction of alpha-substituted nitrophosphonates to phenyl vinyl sulfone catalyzed by cinchona alkaloid-derived tertiary amine-thioureas afforded alpha,alpha-disubstituted nitrophosphonates in very good yields and excellent enantiomeric excesses.
• Quinine-Derived Thiourea and Squaramide Catalyzed Conjugate Addition of α-Nitrophosphonates to Enones: Asymmetric Synthesis of Quaternary α-Aminophosphonates
  作者：Kalisankar Bera、Irishi N. N. Namboothiri

  DOI：10.1021/jo502332r

  日期：2015.2.6

  Conjugate addition of a-nitrophosphonates to enones was carried out in the presence of two sets of organocatalysts, viz. a quinine-thiourea and a quinine-squaramide. The quinine-thiourea provided the products possessing an a-quaternary chiral center in high enantioselectivities only in the case of electron rich enones. On the other hand, the quinine-squaramide was more efficient in that a wide variety of electron rich and electron poor enones underwent Michael addition of nitrophosphonates to afford the quaternary a-nitrophosphonates in excellent yields and enantioselectivities. The hydrogen bonding donor ability of the bifunctional catalyst, as shown in the proposed transition states, appears primarily responsible for the observed selectivity. However, a favorable p-stacking between the aryl groups of thiourea/squaramide and aryl vinyl ketone also appeared favorable. The reaction was amenable to scale up, and the enantioenriched quaternary a-nitrophosphonates could be easily transformed to synthetically and biologically useful quaternary a-aminophosphonates and other multifunctional molecules.