(S)-diethyl furan-2-yl(hydroxy)methylphosphonate | 192701-21-6

• 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: (S)-diethyl furan-2-yl(hydroxy)methylphosphonate
• 英文别名: diethyl (hydroxy)(2-furfuryl)methylphosphonate；(S)-diethoxyphosphoryl(furan-2-yl)methanol
• CAS: 192701-21-6
• 化学式: C₉H₁₅O₅P
• 分子量: 234.189
• InChiKey: RCZYWSRSTXSNHM-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  糠醛 、 亚磷酸二乙酯 在 manganese(II) bromide 、 C₁₀H₁₅N₃O 、 lithium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以43%的产率得到
  参考文献：
  名称：

  锰脯氨酸衍生的新催化剂体系，用于α-羟基膦酸酯和α-氨基膦酸酯的对映选择性合成

  摘要：

  报道了一种新颖的锰/脯氨酸衍生的催化剂体系，用于α-羟基膦酸酯和α-氨基膦酸酯的立体选择性合成。反应在温和的反应条件下以有效的反应时间顺利进行。得到的产物具有高收率和良好的对映选择性（高达83％ee）。

  DOI：

  10.1016/j.tetlet.2017.02.088

文献信息

• Synthesis of an unusual dinuclear chiral iron complex and its application in asymmetric hydrophosphorylation of aldehydes
  作者：Pandi Muthupandi、Govindasamy Sekar

  DOI：10.1039/c2ob25810b

  日期：——

  An unusual dinuclear chiral iron complex has been synthesized and effectively utilized in the asymmetric hydrophosphorylation of aldehydes to synthesize optically active α-hydroxy phosphonates with excellent yield and good enantioselectivity.

  合成了一种不寻常的双核手性铁复合物，并有效地用于醛的非对称氢磷酸化反应，合成了光学活性的α-羟基磷酸酯，产率优秀且对映选择性良好。
• Chiral N,N′-dioxide-Yb(III) complexes catalyzed enantioselective hydrophosphonylation of aldehydes
  作者：Weiliang Chen、Yonghai Hui、Xin Zhou、Jun Jiang、Yunfei Cai、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1016/j.tetlet.2010.05.137

  日期：2010.8

  Chiral N,N'-dioxide-Ytterbium(III) complexes promoted the asymmetric addition of diethyl phosphate to aldehydes, giving the corresponding products with good yields and enantioselectivities. The addition of pyridine favored both reactivity and enantioselectivity. A possible catalytic cycle was proposed to explain the mechanism of the asymmetric hydrophosphonylation of aldehydes. (C) 2010 Elsevier Ltd. All rights reserved.
• Highly Enantioselective Hydrophosphonylation of Aldehydes Catalyzed by Tridentate Schiff Base Aluminum(III) Complexes
  作者：Xin Zhou、Xiaohua Liu、Xu Yang、Deju Shang、Junguo Xin、Xiaoming Feng

  DOI：10.1002/anie.200704116

  日期：2008.1
• Nonenzymatic kinetic resolution of racemic α-hydroxyalkanephosphonates with chiral copper catalyst
  作者：Yosuke Demizu、Atsushi Moriyama、Osamu Onomura

  DOI：10.1016/j.tetlet.2009.07.003

  日期：2009.9

  Kinetic resolution of alpha-hydroxyalkanephosphonates was efficiently performed by benzoylation in the presence of copper(II) triflate and (R,R)-Ph-BOX as a catalyst with excellent s value of up to 286. (C) 2009 Elsevier Ltd. All rights reserved.
• Manganese-proline derived new catalyst system for the enantioselective synthesis of α -hydroxyphosphonates and α -aminophosphonates
  作者：Hyun Lim、Vicklyn Datilus、Rania Teriak、Prianka Chohan、Parminder Kaur

  DOI：10.1016/j.tetlet.2017.02.088

  日期：2017.4

  A novel manganese/proline-derived catalyst system is reported for the stereoselective synthesis of α-hydroxyphosphonates and α-aminophosphonates. The reaction proceeded smoothly under mild reaction conditions with efficient reaction times. The resulting products were obtained with high yields and good enantioselectivities (up to 83% ee).

  报道了一种新颖的锰/脯氨酸衍生的催化剂体系，用于α-羟基膦酸酯和α-氨基膦酸酯的立体选择性合成。反应在温和的反应条件下以有效的反应时间顺利进行。得到的产物具有高收率和良好的对映选择性（高达83％ee）。