diethyl 2-hydroxy-3-phenylpropanephosphonate | 95448-38-7

• 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 2-hydroxy-3-phenylpropanephosphonate
• 英文别名: diethyl 2-hydroxy-3-phenylpropylphosphonate；Phosphonic acid, (2-hydroxy-3-phenylpropyl)-, diethyl ester；1-diethoxyphosphoryl-3-phenylpropan-2-ol
• CAS: 95448-38-7
• 化学式: C₁₃H₂₁O₄P
• 分子量: 272.281
• InChiKey: VQQSLBXXFIFOFG-UHFFFAOYSA-N

物化性质

• 沸点：
  401.4±38.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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 2-hydroxy-3-phenylpropanephosphonate 在 三(2-氯乙基)胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 diethyl (2-azido-3-phenylpropyl)phosphonate
  参考文献：
  名称：

  Gajda, T.; Nowalinska, M.; Zawadzki, S., Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 105, # 1-4, p. 45 - 50

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基膦酸二乙酯 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 diethyl 2-hydroxy-3-phenylpropanephosphonate
  参考文献：
  名称：

  Biocatalytic syntheses of chiral non-racemic 2-hydroxyalkanephosphonates

  摘要：

  A series of 2-oxoalkanephosphonates 2 were screened for reduction with Geotrichum candidum. Only diethyl 2-oxopropanephosphonate 2a underwent asymmetric reduction to give (+)-(R)-diethyl 2-hydroxypropanephosphonate 3a with 98% e.e. In turn, a series of racemic 2-hydroxyalkanephosphonates 3 were acetylated under kinetic resolution conditions in the presence of various lipases to give the corresponding 2-acetoxyalkanephosphonates 4 and recovered alcohols 3 in good yields and with e.e. up to 93%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00567-5

文献信息

• A NEW SYNTHETIC ROUTE OF β-HYDROXYALKYLPHOSPHONATES FROM β,γ-EPOXYALKYLPHOSPHONATES
  作者：Toshio Nagase、Takayuki Kawashima、Naoki Inamoto

  DOI：10.1246/cl.1984.1997

  日期：1984.11.5

  β-Hydroxyalkylphosphonates were synthesized from β,γ -epoxyalkylphosphonates and RMgX/ cat. CuI reagents, which is a new synthetic route for the various types of α- and/or γ-substituted β-hydroxyalkylphosphonates.

  β-羟基烷基磷酸盐是通过β,γ-环氧烷基磷酸盐与RMgX/催化剂CuI试剂合成的，这是一种新的合成不同类型的α和/或γ取代的β-羟基烷基磷酸盐的路线。
• A facile synthesis of β- and γ- hydroxyphosphonate esters from epoxides
  作者：Saibaba Racha、Zhengong Li、Hussein El-Subbagh、Elie Abushanab

  DOI：10.1016/s0040-4039(00)61125-5

  日期：1992.9

  A BF3.OEt2 catalyzed, regiospecific nucleophilic ring opening reaction of epoxides by dialkyl phosphite and methanephosphonate esters is described. The reaction proceeds in good to excellent yields to give the title compounds and is compatible with a variety of other functional groups.

  描述了BF 3 .OEt 2催化的亚磷酸二烷基酯和甲膦酸酯的环氧化物的区域特异性亲核开环反应。反应以良好的收率进行，得到优异的标题化合物，并且与多种其他官能团相容。
• Synthesis of branched 9-[2-(2-phosphonoethoxy)ethyl]purines as a new class of acyclic nucleoside phosphonates which inhibit Plasmodium falciparum hypoxanthine–guanine–xanthine phosphoribosyltransferase
  作者：Dana Hocková、Antonín Holý、Milena Masojídková、Dianne T. Keough、John de Jersey、Luke W. Guddat

  DOI：10.1016/j.bmc.2009.07.044

  日期：2009.9.1

  the salvage enzyme, hypoxanthine–guanine–xanthine phosphoribosyltransferase (HGXPRT), for the synthesis of the 6-oxopurine nucleoside monophosphates. Specific acyclic nucleoside phosphonates (ANPs) inhibit PfHGXPRT and possess anti-plasmodial activity. Two series of novel branched ANPs derived from 9-[2-(2-phosphonoethoxy)ethyl]purines were synthesized to investigate their inhibition of PfHGXPRT and

  疟疾寄生虫恶性疟原虫（Pf）缺乏从头途径，并且依赖挽救酶次黄嘌呤-鸟嘌呤-黄嘌呤磷酸核糖基转移酶（HGXPRT）来合成6-氧代嘌呤核苷一磷酸。特定的无环核苷膦酸酯（ANP）抑制Pf HGXPRT并具有抗疟原虫活性。合成了两个系列的9- [2-（2-膦酰基乙氧基）乙基]嘌呤衍生的新型支链ANP，以研究其对Pf HGXPRT和人HGPRT的抑制作用。Pf HGXPRT的最佳抑制剂具有K i1μM。数据表明，疏水取代基的位置和性质都改变了ANP的效能和选择性。
• Phillips, A. M. M. M.; Mphahlele, M. J.; Modro, A. M., Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 71, p. 165 - 174
  作者：Phillips, A. M. M. M.、Mphahlele, M. J.、Modro, A. M.、Modro, T. A.、Zwierzak, A.

  DOI：——

  日期：——
• NAGASE, TOSHIO;KAWASHIMA, TAKAYUKI;INAMOTO, NAOKI, CHEM. LETT., 1984, N 11, 1997-2000
  作者：NAGASE, TOSHIO、KAWASHIMA, TAKAYUKI、INAMOTO, NAOKI

  DOI：——

  日期：——