diethyl pentanoylphosphonate | 13504-66-0

• 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: diethyl pentanoylphosphonate
• 英文别名: Valerylphosphonsaeurediethylester；1-Diethoxyphosphorylpentan-1-one
• CAS: 13504-66-0
• 化学式: C₉H₁₉O₄P
• 分子量: 222.221
• InChiKey: KTZKWCJEBFFOIT-UHFFFAOYSA-N

物化性质

• 沸点：
  130-132 °C(Press: 10 Torr)
• 密度：
  1.0379 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• 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：

  diethyl pentanoylphosphonate 在 硼烷四氢呋喃络合物 、 三(2-氯乙基)胺 、 水 、 三苯基膦 、 (S)-tetrahydro-1-butyl-3,3-diphenyl-1H,3H-pyrrolo{2,1-c}{1,3,2}oxazaborole 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 29.0h， 生成 (R)-diethyl 1-aminopentylphosphonate
  参考文献：
  名称：

  Enantioselective synthesis of diethyl 1-hydroxyalkylphosphonates via oxazaborolidine catalyzed borane reduction of diethyl α-ketophosphonates

  摘要：

  Reduction of diethyl alpha-ketophosphonates 1 with borane and B-butyloxazaborolidine 2 as catalyst afforded diethyl (S)- or (R)-1-hydroxyalkylphosphonates 3a-d or 3e-f respectively in good yields and moderate to good enantiomeric excess (53-83 ee%). Respective diethyl (R)- and (S)-1-aminoalkylphosphonates 6 were obtained in a one-pot transformation, by the Mitsunobu reaction of 1-hydroxyphosphonates 3 with hydrazoic acid, and subsequent treatment of the intermediate azides 4, with triphenylphosphine, followed by hydrolysis df the iminophosphoranes 5 with water.

  DOI：

  10.1016/s0957-4166(00)86271-0
• 作为产物：
  描述：

  diethyl (1-hydroxypentyl)phosphonate 在 chromium(VI) oxide 、 aluminum oxide 作用下， 反应 10.0h， 以75%的产率得到diethyl pentanoylphosphonate
  参考文献：
  名称：

  Surface-mediated solid-phase reactions: the preparation of acyl phosphonates by oxidation of 1-hydroxyphosphonates on the solid surface

  摘要：

  Alumina-supported CrO3, under solvent-free conditions, was found to be an efficient oxidizing reagent for the preparation of acyl phosphonates from 1-hydroxyphosphonates. This method is an easy, rapid, and high-yielding reaction for the preparation of acyl phosphonates from 1-hydroxyphosphonates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00323-3

文献信息

• Studies on Organophosphorus Compounds, 53: A New Procedure for the Synthesis of 1-Alkyl or 1-Aryl-1-hydroxy-2-nitroethylphoshonates under PTC Conditions
  作者：Chengye Yuan、Shuhua Cui、Guohong Wang、Hanzhen Feng、Deliang Chen、Chaozhong Li、Yixiang Ding、Ludwig Maier

  DOI：10.1055/s-1992-26081

  日期：——

  A series of dialkyl 1-alkyl- or 1-aryl-1-hydroxy-2-nitroethyl-phosphonates and 1-hydroxy-1-(nitromethyl)alkylphosphonates was prepared by nucleophilic addition of nitromethane to dialkyl acylphosphonates in the presence of potassium carbonate and tetrabutylammonium bromide.

  通过在碳酸钾和四丁基溴化铵的存在下，对二烷基酰基磷酸盐进行硝基甲烷的亲核加成，制备了一系列二烷基1-烷基或1-芳基-1-羟基-2-硝基乙基磷酸酯和1-羟基-1-(硝基甲基)烷基磷酸酯。
• Catalytic, Asymmetric Synthesis of Phosphonic γ-(Hydroxyalkyl)butenolides with Contiguous Quaternary and Tertiary Stereogenic Centers
  作者：Marcus Frings、Isabelle Thomé、Ingo Schiffers、Fangfang Pan、Carsten Bolm

  DOI：10.1002/chem.201304331

  日期：2014.2.3

  yielding access to phosphonic γ‐(hydroxyalkyl)butenolides with excellent regio‐, diastereo‐ and enantiocontrol is reported. The simultaneous construction of up to two adjacent quaternary stereogenic centers by a catalytic asymmetric vinylogous Mukaiyama aldol reaction unites biologically and medicinally relevant entities, namely α‐hydroxy phosphonates and γ‐(hydroxyalkyl)butenolides. This is achieved by

  据报道，该方法可高收率地获得具有出色的区域，非对映和对映体控制能力的膦酸γ-（羟烷基）丁烯内酯。催化不对称乙烯基Mukaiyama aldol反应最多可同时构建两个相邻的四级立体异构中心，这些结构在生物学和医学上相关的实体，即α-羟基膦酸酯和γ-（羟烷基）丁烯醇内酯。这是通过利用易于获得的手性铜-亚磺酰亚胺催化剂对亲电子和亲核反应物表现出宽泛的官能团耐受性来实现的。还包括对影响观察到的对映选择性水平的潜在因素的讨论，对映选择性水平来自对映纯的亚砜亚胺配体。
• Synthesis of<i>O</i>,<i>O</i>-Dialkyl 1-Aminoalkanephosphonates
  作者：Z. H. Kudzin、A. Kotyński

  DOI：10.1055/s-1980-29311

  日期：——
• A novel route to .alpha.-aminoalkylphosphonic acids and dialkyl .alpha.-aminoalkylphosphonate hydrochlorides
  作者：K. Darrell Berlin、N. K. Roy、R. T. Claunch、D. Bude

  DOI：10.1021/ja01018a076

  日期：1968.7
• Catalytic Aldol–Cyclization Cascade of 3-Isothiocyanato Oxindoles with α-Ketophosphonates for the Enantioselective Synthesis of β-Amino-α-hydroxyphosphonates
  作者：Satavisha Kayal、Santanu Mukherjee

  DOI：10.1021/acs.orglett.5b02929

  日期：2015.11.6

  A cascade aldol cyclization reaction between 3-isothiocyanato oxindoles and alpha-ketophosphonates has been developed for the synthesis of beta-amino-alpha-hydroxyphosphonate derivatives. Catalyzed by a quinine-based tertiary amino-thiourea derivative, this reaction delivers 2-thioxooxazolidinyl phosphonates based on a spirooxindole scaffold bearing two contiguous quaternary stereogenic centers in high yields with excellent diastereo- (up to >20:1 dr) and enantioselectivities (up to >99:1 er).