(diisopropyl) (2,4-dithiapentamethylene)diphosphonate | 158955-07-8

• 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: (diisopropyl) (2,4-dithiapentamethylene)diphosphonate
• 英文别名: 2-[Di(propan-2-yloxy)phosphorylmethylsulfanylmethylsulfanylmethyl-propan-2-yloxyphosphoryl]oxypropane
• CAS: 158955-07-8
• 化学式: C₁₅H₃₄O₆P₂S₂
• 分子量: 436.511
• InChiKey: BBDLBPDBDRYYHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  493.0±35.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (diisopropyl) (2,4-dithiapentamethylene)diphosphonate 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 生成 (diisopropoxyphosphorylmethanesulfonylmethanesulfonylmethyl)phosphonic acid diisopropyl ester
  参考文献：
  名称：

  A novel reagent for the synthesis of geminal di-sulfones

  摘要：

  A novel reagent (diisopropoxyphosphorylmethanesulfonylmethyl)-phosphonic acid diisopropyl ester (8) capable of forming symmetrical and non-symmetrical alpha,beta unsaturated gem-disulfones is reported. Both aromatic and aliphatic aldehydes react in good yields to give exclusively the trans isomer. Selectivity for the mono-olefin can be achieved by varying the stoichiometry of reagents. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01004-8
• 作为产物：
  描述：

  diisopropyl <(acetylthio)methyl>phosphonate 在 sodium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.5h， 生成 (diisopropyl) (2,4-dithiapentamethylene)diphosphonate
  参考文献：
  名称：

  A novel reagent for the synthesis of geminal di-sulfones

  摘要：

  A novel reagent (diisopropoxyphosphorylmethanesulfonylmethyl)-phosphonic acid diisopropyl ester (8) capable of forming symmetrical and non-symmetrical alpha,beta unsaturated gem-disulfones is reported. Both aromatic and aliphatic aldehydes react in good yields to give exclusively the trans isomer. Selectivity for the mono-olefin can be achieved by varying the stoichiometry of reagents. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01004-8

文献信息

• Reductions of phosphonodithioformates: Syntheses of β-phosphonyl thiols and hemidithioacetals.
  作者：Hubert Makomo、Serge Masson、Monique Saquet

  DOI：10.1016/s0040-4020(01)81760-9

  日期：1994.8

  The phosphonodithioformates appeared versatile precursors to the (mercaptomethyl)phosphonates and derivatives, through sodium borohydride reduction in acetonitrile heated under reflux. By contrast, when the reduction was performed at room temperature with sodium borohydride, the (mercapto-alkylthio-methyl)phosphonates were exclusively obtained; reduction with BH3-Me(2)S (BMS) or within lithium diisopropylaminoborohydride also led to these hemidithioacetals. The aforementioned products of reduction were characterized by the syntheses of various derivatives. In particular, S-phosphonyl trithiocarbonates, N-phenyl imidodithiocarbonate and dithiocarbamate were prepared.
• Synthesis and Biological Evaluation of Geminal Disulfones as HIV-1 Integrase Inhibitors
  作者：D. Christopher Meadows、Timothy B. Mathews、Thomas W. North、Michael J. Hadd、Chih Lin Kuo、Nouri Neamati、Jacquelyn Gervay-Hague

  DOI：10.1021/jm049171v

  日期：2005.7.1

  Integration of HIV-1 viral DNA into the host genome is carried out by HIV-integrase (IN) and is a critical step in viral replication. Although several classes of compounds have been reported to inhibit IN in enzymatic assays, inhibition is not always correlated with antiviral activity. Moreover, potent antiviral IN inhibitors such as the chicoric acids do not act upon the intended enzymatic target but behave as entry inhibitors instead. The charged nature of the chicoric acids contributes to poor cellular uptake, and these compounds are further plagued by rapid ester hydrolysis in vivo. To address these critical deficiencies, we designed neutral, nonhydrolyzable analogues of the chicoric acids. Herein, we report the synthesis, enzyme inhibition studies, and cellular antiviral data for a series of geminal disulfones. Of the 10 compounds evaluated, 8 showed moderate to high inhibition of IN in purified enzyme assays. The purified enzyme data correlated with antiviral assays for all but two compounds, suggesting alternative modes of inhibition. Time-of-addition studies were performed on these analogues, and the results indicate that they inhibit an early stage in the replication process, perhaps entry. In contrast, the most potent member of the correlative group shows behavior consistent with IN being the cellular target.
• A novel reagent for the synthesis of geminal di-sulfones
  作者：Michael J Hadd、Mark A Smith、Jacquelyn Gervay-Hague

  DOI：10.1016/s0040-4039(01)01004-8

  日期：2001.7

  A novel reagent (diisopropoxyphosphorylmethanesulfonylmethyl)-phosphonic acid diisopropyl ester (8) capable of forming symmetrical and non-symmetrical alpha,beta unsaturated gem-disulfones is reported. Both aromatic and aliphatic aldehydes react in good yields to give exclusively the trans isomer. Selectivity for the mono-olefin can be achieved by varying the stoichiometry of reagents. (C) 2001 Published by Elsevier Science Ltd.