2-Octyloxy-[1,3,2]dioxaphospholane 2-oxide | 96720-28-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 2-Octyloxy-[1,3,2]dioxaphospholane 2-oxide
• 英文别名: 2-(Octyloxy)-1,3,2lambda~5~-dioxaphospholan-2-one；2-octoxy-1,3,2λ5-dioxaphospholane 2-oxide
• CAS: 96720-28-4
• 化学式: C₁₀H₂₁O₄P
• 分子量: 236.248
• InChiKey: PBKCJVXMBQUKBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  293.1±7.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  十八烷基二甲基叔胺 、 2-Octyloxy-[1,3,2]dioxaphospholane 2-oxide 以 乙腈 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Zwitterionic Geminis. Coacervate Formation from a Single Organic Compound

  摘要：

  [GRAPHICS]Easily "tunable" zwitterionic gemini surfactants were prepared with a wide variety of chain combinations. These geminis self-assemble into micelles, vesicles, and tubules at low concentrations in water, Two particularly remarkable geminis form a coacervate whose "sponge-like" structure is visible by cryo-high-resolution scanning electron microscopy.

  DOI：

  10.1021/ol990205g
• 作为产物：
  描述：

  辛醇 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 12.5h， 生成 2-Octyloxy-[1,3,2]dioxaphospholane 2-oxide
  参考文献：
  名称：

  A new efficient and versatile synthesis of alkyl prosphorylcholines

  摘要：

  DOI：

  10.1016/s0040-4039(00)98424-7

文献信息

• Interaction between Zwitterionic Surfactants and Amphiphilic Drug: A Tensiometric Study
  作者：Wajid Husain Ansari、Sahar Noori、Andleeb Naqvi、Kabir - ud - Din

  DOI：10.1524/zpch.2012.0340

  日期：2013.4.1

  The physicochemical properties, viz, critical micelle concentration (cmc), surface excess concentration (Γ _max), minimum area per head group (A _min) of zwitterionic surfactants (designated as n(−)-2-m(+); n = 8, 10, 12 and m = 12, 14, 16) and their mixtures with amphiphilic antidepressant drug amitriptyline hydrochloride (AMT) were determined by using surface tension measurements. The cmc and ideal cmc (cmc_id) values along with interaction parameters, β ^m and β ^σ (calculated using Rubingh's and Rosen's models), suggest attractive interactions among the components. The Krafft temperature measurements also indicate strong attractive interactions. Γ _max (or A _min) increases (or decreases) with the addition of gemini surfactant; the values being closer to that of the drug. These values and micellar mole fraction (X₁ ^m-calculated from Rubingh's model and X ₁ ^Moto-calculated from Motomura's model) indicate larger contribution of gemini surfactants in mixed micelles and smaller contribution at air/solution interface (as mole fraction values at interface, X ₁ ^σ , are slightly smaller than X ₁ ^m). The standard Gibbs energy of micellization (Δ G _micº) and adsorption (Δ G _adº) as well as excess energy of mixing (Δ G _ex ^m) are all negative. All these results suggest higher stability of the mixed systems. UV absorbance results also suggest that the mixed micelles are stable for several days.

  物理化学性质，如带电表面活性剂（标记为n(-)-2-m+; n = 8, 10, 12和m = 12, 14, 16）及其与两性抗抑郁药阿米替林盐酸盐（AMT）混合物的临界胶束浓度（cmc）、表面过剩浓度（Γmax）、每个头基最小面积（Amin）通过表面张力测量确定。cmc和理想cmc（cmc id）值以及相互作用参数βm和βσ（使用Rubingh和Rosen模型计算）表明组分之间存在吸引相互作用。Krafft温度测量也表明存在强烈的吸引相互作用。Γmax（或Amin）随着双子表面活性剂的添加而增加（或减少）；这些值接近药物的值。这些值和胶束摩尔分数（X1m-从Rubingh模型计算和X1Moto-从Motomura模型计算）表明双子表面活性剂在混合胶束中的贡献更大，在气液界面的贡献较小（因为界面的摩尔分数值X1σ略小于X1m）。胶束化的标准吉布斯能（ΔGmicº）和吸附（ΔGadº）以及混合的过剩能（ΔGexm）均为负值。所有这些结果表明混合系统的稳定性更高。UV吸收结果还表明混合胶束在几天内是稳定的。
• Effect of Asymmetric Dimeric Zwitterionic Surfactants on Micellization Behavior of Amphiphilic Drugs
  作者：Sahar Noori、Andleeb Z. Naqvi、Wajid H. Ansari、Kabir-ud-Din

  DOI：10.1007/s10953-015-0338-9

  日期：2015.6

  The micellization process in mixtures of amphiphilic drugs and asymmetric dimeric zwitterionic surfactants have been investigated tensiometrically. The drugs used are from two families: imipramine hydrochloride (IMP)—a tricyclic antidepressant and ibuprofen (IBF)—a nonsteroidal antiinflammatory drug, whereas zwitterionic dimeric surfactants are heterogemini surfactants that contain quaternary ammonium and phosphate groups as heads. The results show that the cmc of drug-surfactant mixtures decreases with the increase in stoichiometric mole fraction of surfactants (α 1), suggesting attractive interaction among the two components. This is supported by the values of cmc id (critical micelle concentration values for ideal mixing) which are always greater than experimental cmc values. Also, the decrease in magnitude is more in IBF–dimeric surfactant mixed systems than in IMP–dimeric surfactant mixed systems. Micellar mole fraction values, obtained using Rubingh’s ( $$ X_\text1}}^\textm}} $$ ) and Motomura’s ( $$ X_\text1}}^\textm}} $$ ) models, are lower than the micellar mole fraction for ideal mixing ( $$ X_\text1}}^\textid}}} $$ ). The micellar interaction parameter ( $$ \beta^\textm}} $$ ) follows the order: 8(−)−2−16(+) > 10(−)−2−16(+) > 10(−)−2−14(+) > 8(−)−2−14(+). The results are explained on the basis of difference in tail lengths. Interfacial mole fraction ( $$ X_\text1}}^\upsigma} $$ ) values, evaluated using Rosen’s model, are higher than $$ X_\text1}}^\textm}} $$ values for IMP-10(−)−2−16(+) and IMP-10(−)−2−14(+) systems while for all other systems (except 8(−)−2−14(+)) the values are smaller than $$ X_\text1}}^\textm}} $$ . The interaction parameter at the interface ( $$ \beta^\upsigma} $$ ) is negative and $$ \beta_av}^\textm}} $$ values are greater than $$ \beta_av}^\upsigma} $$ in magnitude. All the results indicate that the dimeric surfactants are mostly in cationic form.

  通过表面张力法研究了两性药物与非对称二聚两性离子表面活性剂混合体系中的胶束化过程。所用药物分别来自两类：咪帕明盐酸盐（IMP）—一种三环类抗抑郁药和布洛芬（IBF）—一种非甾体抗炎药，而两性离子二聚表面活性剂则是包含季铵和磷酸基团作为头基的杂双子表面活性剂。结果表明，药物-表面活性剂混合体系的临界胶束浓度随表面活性剂的计量摩尔分数（α1）的增加而降低，表明两种组分之间存在吸引相互作用。这可通过临界胶束浓度值（cmc id，理想混合物的临界胶束浓度）总是大于实验临界胶束浓度值得到支持。此外，IBF-二聚表面活性剂混合体系的降低幅度比IMP-二聚表面活性剂混合体系的降低幅度更大。通过Rubingh模型（ $$ X_\text1}}^\textm}} $$ ）和Motomura模型（ $$ X_\text1}}^\textm}} $$ ）得到的胶束摩尔分数值低于理想混合的胶束摩尔分数（ $$ X_\text1}}^\textid}}} $$ ）。胶束相互作用参数（ $$ \beta^\textm}} $$ ）遵循以下顺序：8(-)−2−16(+) > 10(-)−2−16(+) > 10(-)−2−14(+) > 8(-)−2−14(+)。结果基于尾部长度的差异进行解释。使用Rosen模型评估的界面摩尔分数（ $$ X_\text1}}^\upsigma} $$ ）值，对于IMP-10(-)−2−16(+)和IMP-10(-)−2−14(+)系统，这些值高于 $$ X_\text1}}^\textm}} $$ 值，而对于所有其他系统（除了8(-)−2−14(+)），这些值小于 $$ X_\text1}}^\textm}} $$ 。界面相互作用参数（ $$ \beta^\upsigma} $$ ）为负值，并且 $$ \beta_av}^\textm}} $$ 值的绝对值大于 $$ \beta_av}^\upsigma} $$ 。所有结果表明，二聚表面活性剂主要以阳离子形式存在。
• Zwitterionic Phospholipidation of Cationic Polymers Facilitates Systemic mRNA Delivery to Spleen and Lymph Nodes
  作者：Shuai Liu、Xu Wang、Xueliang Yu、Qiang Cheng、Lindsay T. Johnson、Sumanta Chatterjee、Di Zhang、Sang M. Lee、Yehui Sun、Ting-Chih Lin、John L. Liu、Daniel J. Siegwart

  DOI：10.1021/jacs.1c09822

  日期：2021.12.22

  Polymers represent a promising therapeutic platform for extrahepatic messenger RNA (mRNA) delivery but are hampered by low in vivo efficacy due to polyplex serum instability and inadequate endosomal escape following systemic administration. Here, we report the rational design and combinatorial synthesis of zwitterionic phospholipidated polymers (ZPPs) via cationic polymer postmodification by alkylated

  聚合物代表了一种有前途的肝外信使 RNA (mRNA) 递送治疗平台，但由于多聚物血清不稳定和全身给药后内体逃逸不足，体内疗效低下而受到阻碍。在这里，我们报告了两性离子磷脂化聚合物 (ZPP) 的合理设计和组合合成，通过烷基化二氧杂磷烷氧化物的阳离子聚合物后修饰，在体内将 mRNA 递送至脾脏和淋巴结. 这种模块化的后修饰方法很容易产生可调节的两性离子物种以实现血清抗性，并同时引入烷基链以增强内体逃逸，从而将有缺陷的阳离子聚合物转化为有效的两性离子 mRNA 载体，而无需精心合成功能单体。ZPPs在体外介导的蛋白质表达比其母体阳离子对应物高 39500 倍，并且在体内静脉内给药后能够选择性地在脾脏和淋巴结中有效地递送 mRNA. 这种两性离子磷脂化方法提供了一种通用且可推广的后修饰策略，可将两性离子引入阳离子聚合物的侧链，扩展了阳离子聚合物家族在精确递送 mRNA 方面的用途，并展示了免疫治疗应用的巨大潜力。
• A Modular Synthesis of Alkynyl-Phosphocholine Headgroups for Labeling Sphingomyelin and Phosphatidylcholine
  作者：Mahendra S. Sandbhor、Jessie A. Key、Ileana S. Strelkov、Christopher W. Cairo

  DOI：10.1021/jo901824h

  日期：2009.11.20

  A general route to phospho- and sphingolipids that incorporate an alkyne in the phosphocholine headgroup is described. The strategy preserves the ammonium functionality of the phosphocholine and call be easily modified to introduce desired functional groups at the N-acyl chain. The targets accessible with this strategy provide a bioorthogonal handle for postsynthetic introduction of fluorophores or other labeling agents with aqueous phase chemistry. We report the synthesis of sphingomyelin derivatives that incorporate a fluorophore and an alkyne. The modified sphingolipids retain activity as substrates for sphingomyelinase, making these compounds viable probes of enzymatic activity. Importantly, the strategy allows modification of the lipid across the phosphodiester, making the alkyne a potential probe of sphingomyelinase activity.
• A Combinatorially-Derived Structural Phase Diagram for 42 Zwitterionic Geminis
  作者：Fredric M. Menger、Andrey V. Peresypkin

  DOI：10.1021/ja003779l

  日期：2001.6.1