diethyl (1-hydroxy-3-methyl-2-butenyl)phosphonate | 149794-32-1

• 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: diethyl (1-hydroxy-3-methyl-2-butenyl)phosphonate
• 英文别名: diethyl 1-hydroxy-3-methylbut-2-enylphosphonate；1-Diethoxyphosphoryl-3-methylbut-2-en-1-ol
• CAS: 149794-32-1
• 化学式: C₉H₁₉O₄P
• 分子量: 222.221
• InChiKey: YDVIXAMYHNCDLH-UHFFFAOYSA-N

物化性质

• 沸点：
  305.9±35.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (1-hydroxy-3-methyl-2-butenyl)phosphonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 盐酸 、 methyloxirane 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 19.25h， 生成 ((E)-3-Amino-3-methyl-but-1-enyl)-phosphonic acid
  参考文献：
  名称：

  Ohler; Kotzinger, Synthesis, 1993, # 5, p. 497 - 502

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl (3-methyl-1-oxo-2-butenyl)phosphonate 在 sodium tetrahydroborate 、 potassium dihydrogenphosphate 作用下， 以 水 为溶剂， 反应 0.42h， 以95%的产率得到diethyl (1-hydroxy-3-methyl-2-butenyl)phosphonate
  参考文献：
  名称：

  Ohler; Kotzinger, Synthesis, 1993, # 5, p. 497 - 502

  摘要：

  DOI：

文献信息

• Novel Lanthanide Amides Incorporating Neutral Pyrrole Ligand in a Constrained Geometry Architecture: Synthesis, Characterization, Reaction, and Catalytic Activity
  作者：Fenhua Wang、Shaowu Wang、Xiancui Zhu、Shuangliu Zhou、Hui Miao、Xiaoxia Gu、Yun Wei、Qingbing Yuan

  DOI：10.1021/om400409x

  日期：2013.7.22

  The first series of lanthanide amido complexes incorporating a neutral pyrrole ligand in a constrained geometry architecture were synthesized, and their bonding, reactions, and catalytic activities were studied. Treatment of [(Me3Si)2N]3Ln(μ-Cl)Li(THF)3 with 1 equiv of (N-C6H5NHCH2CH2)(2,5-Me2C4H2N) (1) afforded the first example of bisamido lanthanide complexes having the neutral pyrrole η5-bonded

  合成了在受限几何结构中结合中性吡咯配体的第一系列镧系酰胺配合物，并研究了它们的键合，反应和催化活性。的治疗[（ME 3 Si）的2 N] 3 LN（μ-Cl）的锂（THF）3与1的（当量Ñ -C 6 ħ 5 NHCH 2 CH 2）（2,5-ME 2 c ^ 4 ħ 2 N）（1），得到具有中性吡咯η双酰胺镧系络合物的第一例5键合的，以配制成[η金属5：η 1-（N -C 6 H 5 NCH 2 CH 2）（2,5-Me 2 C 4 H 2 N）] Ln [N（SiMe 3）2 ] 2（Ln = La（2）和Nd（3）） 。的反应[（ME 3 Si）的2 N] 3的Sm（μ-Cl）的锂（THF）3与2当量的1产生的复杂的[η 5：η 1 - （Ñ -C 6 ħ 5 NCH 2 CH 2） （2,5-我2c ^ 4 ħ 2 N）] [η 1 - （Ñ -C 6 ħ 5 NCH 2 CH 2）（2
• Triflic acid mediated functionalization of α-hydroxyphosphonates: route for sulfonamide phosphonates
  作者：Gangaram Pallikonda、Manab Chakravarty

  DOI：10.1039/c3ra43823f

  日期：——

  An operationally simple synthetic method for (±)-α-aryl/methylsulfonamidomethylphosphonates and new (±)-γ-aryl/methyl sulfonamidomethylvinylphosphonates has been developed through straightforward reactions of (±)-α-hydroxyphosphonates with sulfonamides in the presence of triflic acid (TfOH) at room temperature in a vessel open to air. For γ-dimethylallylhydroxyphosphonate, the (E)-1,3-butadienylphosphonate was formed quantitatively using TfOH while FeCl3 afforded the expected product in moderate yield unpredictably. The favourable sulfonoamidation of benzyl alcohol is also observed when TfOH was used for α-hydroxyphosphonates having a benzyloxy group.

  通过在室温下，在三氟甲磺酸（TfOH）存在下，将（±）-α-羟基膦酸与磺酰胺在开放容器中进行简单反应，开发了一种用于合成（±）-α-芳基/甲基磺酰胺甲基膦酸酯和新型（±）-γ-芳基/甲基磺酰胺甲基乙烯基膦酸酯的操作简便的合成方法。对于γ-二甲基烯丙基羟基膦酸，TfOH定量地形成（E）-1,3-丁二烯基膦酸，而FeCl3则以中等产率不可预测地得到了预期产物。当TfOH用于含有苄氧基的α-羟基膦酸时，也观察到苄醇的有利磺酰胺化。
• An efficient synthesis of (Z)-γ-fluoroallylphosphonates using a base-promoted deconjugation of (E)-γ-fluorovinylphosphonates, and its utility as fluoroolefin-containing building block
  作者：Gerald B. Hammond、Daniel J. deMendonca

  DOI：10.1016/s0022-1139(99)00244-4

  日期：2000.3

  A three-step synthesis of γ-fluoroallylphosphonates starting with α,β-unsaturated aldehydes is described. Treatment with diethyl phosphite in the presence of KF gives α-hydroxyallyl phosphonate in excellent yield; DAST deoxofluorination produces the corresponding γ-fluorovinylphosphonate through a SN2′ mechanism, and finally, a base-promoted double bond migration leads to the desired γ-fluoroallylphosphonate

  描述了一种以α，β-不饱和醛为原料的γ-氟代烯丙基膦酸酯的三步合成法。在KF存在下用亚磷酸二乙酯处理得到α-羟基烯丙基膦酸酯，收率极好。DAST脱氧氟化通过S N 2'机制产生相应的γ-氟乙烯基膦酸酯，最后，碱促进的双键迁移导致所需的γ-氟代烯丙基膦酸酯。γ-氟代烯丙基膦酸酯是合成氟烯烃的有用组成部分。一项探索性研究得出了（Z）-二乙基1-苄基-3-氟-2-丁烯基膦酸酯和（Z）-二乙基1,3-二氟-2-己烯基膦酸酯的优异产率。LiN（TMS）2处理（E）3-氟-2-己烯基膦酸二乙酯和苯甲醛在THF导致优先形成的顺式- （ż） -二乙基-3-氟-1-（羟基苄基）-2- butenylphosphonate。
• New ω-ketovinyl phosphonates: inexpensive synthesis, isomerization studies and route for functionalized 1,3-butadienes
  作者：Gangaram Pallikonda、Swamy Maloth、Sathish Kumar Kurapati、M. Zubair Khalid Baig、Akhil Raj Kumar Saraswathi、Subhas Ghosal、Manab Chakravarty

  DOI：10.1016/j.tet.2015.06.064

  日期：2015.8

  A straightforward and inexpensive synthetic protocol to access new omega-ketovinyl phosphonates is established from the Lewis or Bronsted acid mediated reactions of alpha-hydroxy allylic phosphonates with aromatic 1,3-diketones. Predominantly, FeCl3 or FeCl3 center dot 6H(2)O has been preferred as easily available, inexpensive and efficient Lewis acid under solvent-free conditions. With experimental and theoretical support, we have demonstrated that some of the substituted open chain 1,3-diketones may exist predominantly in the keto form. Mild base mediated isomerization reactions for omega-ketovinyl phosphonates were carried out to generate corresponding allylic phosphonates. Utility of one of the allylic phosphonates in Horner-Wadsworth-Emmons (HWE) reactions facilitated access to variety of densely substituted 1,3-butadienes attached with 1,3-diketone functionality at the terminal carbon. (C) 2015 Elsevier Ltd. All rights reserved.
• Ohler; Kotzinger, Synthesis, 1993, # 5, p. 497 - 502
  作者：Ohler、Kotzinger

  DOI：——

  日期：——