二丙基丙基膦酸酯 | 1789-95-3

• 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
• 中文名称: 二丙基丙基膦酸酯
• 中文别名: 丙基磷羧酸二丙酯
• 英文名称: dipropyl propylphosphonate
• 英文别名: Propyl-phosphonsaeure-dipropylester；Dipropyl-propylphosphonat；Propylphosponsaeure-dipropylester；1-[propoxy(propyl)phosphoryl]oxypropane
• CAS: 1789-95-3
• 化学式: C₉H₂₁O₃P
• 分子量: 208.238
• InChiKey: KETARUSDLXXJCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  二丙基丙基膦酸酯 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Discovery of phosphonamidate IDO1 inhibitors for the treatment of non-small cell lung cancer

  摘要：

  Targeting indoleamine 2,3-dioxygenase 1 (IDO1) has been identified as an attractive approach for the development of cancer immunotherapy. In this study, a series of phosphonamidate ester containing compounds were designed, synthesized and evaluated for their inhibitory activities against IDOL. Among them, compounds 16,17, and 26 with good IDO1 inhibitory (HeLa IDO1 IC50 = 10-21 nM, hIDO1 IC50 = 78 -121 nM) activities were selected for further investigation and showed good physicochemical properties. Furthermore, based on comparable PK profile and excellent IDO2/TDO inhibitory potency, representative compound 16 was selected for further bio-evaluation and characterized with good efficacy in suppressing lung metastasis (77% inhibition rate) of Lewis cells in vivo. Thus, compound 16 could be a potential and efficacious agent for further evaluation. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111629
• 作为产物：
  描述：

  生成 二丙基丙基膦酸酯
  参考文献：
  名称：

  Pudovik,A.N.; Tarasova,R.I., Journal of general chemistry of the USSR, 1964, vol. 34, p. 1142 - 1146

  摘要：

  DOI：

文献信息

• Microwave-Assisted Ionic Liquid-Catalyzed Selective Monoesterification of Alkylphosphonic Acids—An Experimental and a Theoretical Study
  作者：Nikoletta Harsági、Réka Henyecz、Péter Ábrányi-Balogh、László Drahos、György Keglevich

  DOI：10.3390/molecules26175303

  日期：——

  It is well-known that the P-acids including phosphonic acids resist undergoing direct esterification. However, it was found that a series of alkylphoshonic acids could be involved in monoesterification with C2–C4 alcohols under microwave (MW) irradiation in the presence of [bmim][BF4] as an additive. The selectivity amounted to 80–98%, while the isolated yields fell in the range of 61–79%. The method developed is a green method for P-acid esterification. DFT calculations at the M062X/6–311+G (d,p) level of theory (performed considering the solvent effect of the corresponding alcohol) explored the three-step mechanism, and justified a higher enthalpy of activation (160.6–194.1 kJ·mol−1) that may be overcome only by MW irradiation. The major role of the [bmim][BF4] additive is to increase the absorption of MW energy. The specific chemical role of the [BF4] anion of the ionic liquid in an alternative mechanism was also raised by the computations.

  众所周知，包括膦酸在内的P-酸不易直接酯化。然而，发现一系列烷基膦酸在微波（MW）辐射下与C2-C4醇在[bmim][BF4]存在下可以进行单酯化反应。选择性达到80-98％，而分离收率在61-79％的范围内。所开发的方法是一种绿色的P-酸酯化方法。在M062X/6-311+G(d,p)理论水平上进行的DFT计算（考虑了相应醇的溶剂效应）探索了三步机制，并证明了较高的活化焓（160.6-194.1 kJ·mol-1），只有通过MW辐射才能克服。[bmim][BF4]添加剂的主要作用是增加MW能量的吸收。计算还提出了离子液体中[BF4]阴离子的特定化学作用在另一种机制中的作用。
• An efficient method for the esterification of phosphonic and phosphoric acids using silica chloride
  作者：Manisha Sathe、Arvind K. Gupta、M.P. Kaushik

  DOI：10.1016/j.tetlet.2006.02.159

  日期：2006.5

  Silica chloride is used as an effective heterogeneous catalyst for the rapid esterification of alkyl/aryl phosphonic/phosphoric acids to their corresponding alkyl/aryl phosphonates/phosphates under mild conditions with quantitative yields.

  氯化硅被用作有效的非均相催化剂，用于在温和条件下以定量收率将烷基/芳基膦酸/磷酸快速酯化为其相应的烷基/芳基膦酸酯/磷酸盐。
• <i>p</i>-Toluenesulfonic Acid–Celite as a Reagent for Synthesis of Esters of Alkylphosphonic Acids under Solvent-Free Conditions
  作者：Arvind K. Gupta、Rajesh Kumar、Devendra K. Dubey、M.P. Kaushik

  DOI：10.3184/030823407x218066

  日期：2007.6

  The coupling reaction of alkylphosphonic acids and alcohols on the surface of p-toluenesulfonic acid–Celite under mild and solvent-free conditions gave the corresponding phosphonates in excellent yields. This method provides a useful rapid synthesis of phosphonates for use in the unambiguous identification of chemical warfare agents.

  在温和且无溶剂的条件下，烷基膦酸和醇在对甲苯磺酸-硅藻土表面的偶联反应以优异的产率得到相应的膦酸酯。该方法提供了一种有用的膦酸盐快速合成方法，可用于明确鉴定化学战剂。
• Physical properties and chemical constitution. Part XLIX. The refractivities, densities, and surface tensions of some organophosphorus compounds
  作者：A. A. Foxton、G. H. Jeffery、A. I. Vogel

  DOI：10.1039/j19660000249

  日期：——

  Pure samples of tri-n-alkyl phosphites, di-n-alkyl phosphonates, di-n-propyl n-alkylphosphonates, di-n-alkyl ethylphosphonates (methyl to octyl) of tri-n-alkyl orthophosphates (butyl to heptyl), of tri-2-n-alkoxyethyl phosphites (methoxy- to hexyloxy-), of di-2-n-alkoxyethyl phosphonates (methoxy- to heptyloxy-) and of 2-n-alkoxy-4-methyl- 1,3,2-dioxaphospholans (methoxy- to hexyloxy-) have been prepared

  亚磷酸三正烷基酯，正膦酸二正烷基酯，正烷基膦酸二正丙基酯，正磷酸三正烷基酯（丁基至庚基）的正膦酸二正烷基酯（甲基至辛基），亚磷酸三-2-正烷氧基乙基酯（甲氧基-己氧基），亚磷酸二-2-正烷氧基乙基酯（甲氧基-庚氧基-）和2-正烷氧基-4-甲基-1,3,2已经制备了-二氧杂膦酸酯（甲氧基-至己氧基-），并确定了它们在20°的折射率以及在一定温度范围内的密度和表面张力：详细测量了许多代表性化合物的红外光谱。键（P O），（P–O），（P–C），（P–H）和1,3,2-二氧杂膦环的抛物线，折射和分子折射系数已通过新的实验数据。
• 一种坦西莫司衍生物
  申请人：鲁南制药集团股份有限公司

  公开号：CN114057793A

  公开（公告）日：2022-02-18

  本发明属于医药化工领域，具体涉及一种坦西莫司衍生物；所述坦西莫司衍生物制备方法包括惰性气体保护，化合物VI和化合物VII加入有机溶剂中，加入有机碱，控温反应，TLC检测，反应完毕，加入溶液稀释，无水硫酸钠干燥，减压浓缩，得化合物I；提供一种新中间体化合物VI，可有效提高雷帕霉素酯化反应的区域选择性，有利于42位羟基的反应，可有效避免31位羟基的反应。