dimethyl (1-chloro-2-oxopropyl)phosphonate | 1352401-31-0

• 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: dimethyl (1-chloro-2-oxopropyl)phosphonate
• 英文别名: 1-Chloro-1-dimethoxyphosphorylpropan-2-one
• CAS: 1352401-31-0
• 化学式: C₅H₁₀ClO₄P
• 分子量: 200.559
• InChiKey: CQYXKGJQAZKGPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  dimethyl (1-chloro-2-oxopropyl)phosphonate 在 葡萄糖 作用下， 以97%的产率得到syn-(1R,2S)-dimethyl 1-chloro-2-hydroxypropanephosphonate
  参考文献：
  名称：

  Asymmetric synthesis of (−)-fosfomycin and its trans-(1S,2S)-diastereomer using a biocatalytic reduction as the key step

  摘要：

  Fosfomycin is a gram positive and gram negative antibiotic that contains an asymmetric epoxide. An enzyme library was screened for its ability to reduce dimethyl(1-chloro-2-oxopropyl)phosphonate to the corresponding asymmetric chlorohydrin. Homology models were built in MOE, which were shown to accurately model the enzyme-substrate complex displaying the stereoselectivity that we observed. Two enzymes, YDR368w and YHR104w, were chosen for the scale up and synthesis of fosfomycin and its trans-(1S,2S)-diastereomer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.009
• 作为产物：
  描述：

  丙酮基膦酸二甲酯 在 磺酰氯 作用下， 以 氯仿 为溶剂， 反应 1.08h， 以63%的产率得到dimethyl (1-chloro-2-oxopropyl)phosphonate
  参考文献：
  名称：

  Asymmetric synthesis of (−)-fosfomycin and its trans-(1S,2S)-diastereomer using a biocatalytic reduction as the key step

  摘要：

  Fosfomycin is a gram positive and gram negative antibiotic that contains an asymmetric epoxide. An enzyme library was screened for its ability to reduce dimethyl(1-chloro-2-oxopropyl)phosphonate to the corresponding asymmetric chlorohydrin. Homology models were built in MOE, which were shown to accurately model the enzyme-substrate complex displaying the stereoselectivity that we observed. Two enzymes, YDR368w and YHR104w, were chosen for the scale up and synthesis of fosfomycin and its trans-(1S,2S)-diastereomer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.009

文献信息

• Chemodivergent Photocatalytic Synthesis of Dihydrofurans and β,γ‐Unsaturated Ketones
  作者：Arianna Quintavalla、Ruben Veronesi、Davide Carboni、Ada Martinelli、Nelsi Zaccheroni、Liviana Mummolo、Marco Lombardo

  DOI：10.1002/adsc.202100260

  日期：2021.7

  A synthetic procedure, catalysed by Ir(ppy)3 under visible-light irradiation, for the chemodivergent synthesis of 2,3-dihydrofurans (3) or β,γ-unsaturated ketones (7) starting from α-halo ketones (1) and alkenes (2) has been developed. The mild reaction conditions and the redox-neutral nature of the process make it particularly sustainable avoiding the use of both sacrificial reactants and stoichiometric

  在可见光照射下由 Ir(ppy) 3催化的合成方法，用于从 α-卤代酮 ( 1 ) 和2,3-二氢呋喃 ( 3 ) 或 β,γ-不饱和酮 ( 7 )化学发散合成烯烃 ( 2 ) 已被开发。该过程的温和反应条件和氧化还原中性性质使其特别可持续，避免使用牺牲反应物和化学计量强氧化剂。在 DFT 计算的支持下，仔细的实验​​研究允许详细披露可能的机制途径，并将合成化学趋向于3或7，不仅取决于基材的性质，还取决于实验条件的选择。
• Org. Biomol. Chem. 2003, 1, 3564-3569
  作者：

  DOI：——

  日期：——
• US5532402A
  申请人：——

  公开号：US5532402A

  公开（公告）日：1996-07-02
• Asymmetric synthesis of (−)-fosfomycin and its trans-(1S,2S)-diastereomer using a biocatalytic reduction as the key step
  作者：Christian P. Marocco、Erik V. Davis、Julie E. Finnell、Phung-Hoang Nguyen、Scott C. Mateer、Ion Ghiviriga、Clifford W. Padgett、Brent D. Feske

  DOI：10.1016/j.tetasy.2011.10.009

  日期：2011.10

  Fosfomycin is a gram positive and gram negative antibiotic that contains an asymmetric epoxide. An enzyme library was screened for its ability to reduce dimethyl(1-chloro-2-oxopropyl)phosphonate to the corresponding asymmetric chlorohydrin. Homology models were built in MOE, which were shown to accurately model the enzyme-substrate complex displaying the stereoselectivity that we observed. Two enzymes, YDR368w and YHR104w, were chosen for the scale up and synthesis of fosfomycin and its trans-(1S,2S)-diastereomer. (C) 2011 Elsevier Ltd. All rights reserved.