1-[(2-oxo-1,3,2-dioxaphospholan-2-yl)oxy]dodecane | 96720-29-5

• 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: 1-[(2-oxo-1,3,2-dioxaphospholan-2-yl)oxy]dodecane
• 英文别名: 2-(Dodecyloxy)-1,3,2lambda~5~-dioxaphospholan-2-one；2-dodecoxy-1,3,2λ5-dioxaphospholane 2-oxide
• CAS: 96720-29-5
• 化学式: C₁₄H₂₉O₄P
• 分子量: 292.356
• InChiKey: STDHNXYQKKSXPO-UHFFFAOYSA-N

物化性质

• 沸点：
  358.1±9.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  12
• 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 、 1-[(2-oxo-1,3,2-dioxaphospholan-2-yl)oxy]dodecane 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  42个两性离子双子星的组合派生结构相图。

  摘要：

  DOI：

  10.1021/ja003779l
• 作为产物：
  描述：

  十二烷醇 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 12.5h， 生成 1-[(2-oxo-1,3,2-dioxaphospholan-2-yl)oxy]dodecane
  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。
• Synthesis and Properties of Alkyl Phosphorylcholine Amphiphiles with a Linear and an Asymmetrically Branched Alkyl Chain
  作者：Eui-Chul Kang、Shingo Kataoka、Kenji Kato

  DOI：10.1246/bcsj.78.1558

  日期：2005.8

  Alkyl phosphorylcholine amphiphiles bearing one linear chain and one asymmetrically branched alkyl chain were successfully synthesized using 2-chloro-2-oxo-1,3,2-dioxaphospholane in tetrahydrofuran or ethyl acetate. 1H and 31P NMR studies revealed that the linear alkyl phosphorylcholines (Cn-PC) provide aqueous micelles in D2O and reverse micelles in CDCl3, while the branched alkyl phosphorylcholines (ISOFOLn-PC) give vesicles in D2O. The critical micelle concentrations (CMCs) of Cn-PC were measured by fluorescence dye solubilization methods: the CMCs of C12-PC, C14-PC, C16-PC, and C18-PC were 1.6, 0.38, 0.16, and 0.11 mM, respectively, in water at 25 °C. The critical association concentrations (CACs) of ISOFOL16-PC, ISOFOL20-PC, and ISOFOL24-PC were 0.068, 0.005, and 0.077 mM, respectively, in water at 25 °C. The vesicle size of ISOFOLn-PC in aqueous solution was measured by the dynamic light scattering method. The mean diameter of ISOFOLn-PC vesicles was approximately 30 nm and the size distribution was relatively monodisperse. The ISOFOLn-PC vesicles formed were colloidally stable in water over the period of several weeks.

  成功合成了具有一条直链和一条不对称支链烷基链的烷基膦酰胆碱两亲物，使用2-氯-2-氧代-1,3,2-二氧磷环在四氢呋喃或乙酸乙酯中进行合成。1H和31P核磁共振研究表明，直链烷基膦酰胆碱（Cn-PC）在D2O中提供水溶胶束，在CDCl3中提供反向胶束，而支链烷基膦酰胆碱（ISOFOLn-PC）在D2O中形成囊泡。通过荧光染料溶解方法测定了Cn-PC的临界胶束浓度（CMCs）：在25°C的水中，C12-PC、C14-PC、C16-PC和C18-PC的CMCs分别为1.6、0.38、0.16和0.11 mM。在25°C的水中，ISOFOL16-PC、ISOFOL20-PC和ISOFOL24-PC的临界缔合浓度（CACs）分别为0.068、0.005和0.077 mM。通过动态光散射方法测量了ISOFOLn-PC在水溶液中的囊泡大小。ISOFOLn-PC囊泡的平均直径约为30 nm，尺寸分布相对单一。ISOFOLn-PC囊泡在水溶液中形成，具有几周时间的胶体稳定性。
• Polymer non-aqueous dispersion, process for preparing the same and coating composition formulated therewith
  申请人：NIPPON OIL AND FATS COMPANY, LIMITED

  公开号：EP0305060A2

  公开（公告）日：1989-03-01

  A process for preparing polymer non-aqueous dispersions to be formulated together with a binder component in coating compositions, which comprises the steps of: (1) emulsion polymerizing a hydroxy group containing α,β-ethylenically unsaturated monomer, a polyfunctional α,β-ethylenically unsaturated monomer and an α,β-ethylenically unsaturated monomer different therefrom by using a water-soluble polymerization initiator, preferably a persulphate, in a soap free system or in the presence of an ester group containing anionic or cationic surfactant; adding an organic solvent, preferably comprising an amphipathic organic solvent, to a resultant polymer aqueous dispersion; and then adding a basic compound catalyst when the anionic surfactant is used or an acidic compound catalyst when the cationic surfactant is used, to thereby hydrolyze completely said surfactant and water-soluble polymerization initiator at a temperature not exceeding 95°C as in the condition of suspension; (2) adding an acidic or basic compound to said suspension to neutralize said basic or acidic compound catalyst: then after adding dispersion stabilizing resin, further adding an amine salt of organic acid, followed by leaving said suspension to stand to separate into organic and water layers; and isolating the organic layer from the water layer; and (3) removing residual water in the organic layer. The resultant polymer non-­aqueous dispersion comprises polymer particles having a total ionic group concentration (I) less than 2x10⁻⁵ mol/g particle, a hexane tolerance (HT) from 5 to 40 exclusive and a degree of swelling in acetone (S) less than 10, and used with a binder component comprising a polyol resin and a curing agent for preparing coating compositions.

  一种制备聚合物非水分散体的工艺，该分散体将与粘合剂组分一起配制成涂料组合物，该工艺包括以下步骤：(1) 使用水溶性聚合引发剂（最好是过硫酸盐），在无皂体系中或在含有阴离子或阳 离子表面活性剂的酯基存在下，乳液聚合含羟基的 α、β-乙烯基不饱和单体、多官能团 α、β-乙烯基不饱和单体和与之不同的 α、β-乙烯基不饱和单体；在得到的聚合物水分散液中加入有机溶剂，最好是两性有机溶剂；(2) 向所述悬浮液中加入酸性或碱性化合物，以中和所述碱性或酸性化合物催化剂：(3) 去除有机层中的残留水。由此得到的聚合物非水分散体包含总离子基团浓度（I）小于 2x10-⁵ mol/g 颗粒、正己烷耐受性（HT）从 5 到 40 不等且在丙酮中的溶胀度（S）小于 10 的聚合物颗粒，并与由多元醇树脂和固化剂组成的粘合剂成分一起用于制备涂料组合物。
• 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。
• Zwitterionic Geminis. Coacervate Formation from a Single Organic Compound
  作者：Andrey V. Peresypkin、Fredric M. Menger

  DOI：10.1021/ol990205g

  日期：1999.11.1

  [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.