2-[N-tert-butyl-N-(1-diethoxyphosphoryl-2,2-dimethylpropyl)aminoxy]propionic acid | 540770-92-1

• 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: 2-[N-tert-butyl-N-(1-diethoxyphosphoryl-2,2-dimethylpropyl)aminoxy]propionic acid
• 英文别名: 2-[Tert-butyl-(1-diethoxyphosphoryl-2,2-dimethylpropyl)amino]oxypropanoic acid
• CAS: 540770-92-1
• 化学式: C₁₆H₃₄NO₆P
• 分子量: 367.423
• InChiKey: DBCQPMVLXCFHMG-UHFFFAOYSA-N

物化性质

• 沸点：
  442.8±55.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[N-tert-butyl-N-(1-diethoxyphosphoryl-2,2-dimethylpropyl)aminoxy]propionic acid 在 4-二甲氨基吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 16.75h， 生成 Cyclohex-2-en-1-yl 2-[tert-butyl-(1-diethoxyphosphoryl-2,2-dimethylpropyl)amino]oxypropanoate
  参考文献：
  名称：

  SG1 based alkoxyamines as radical initiators for the synthesis of lactones and lactames

  摘要：

  Recently, it has been shown that alkoxyamines can be used as radical initiators in tin-free radical chemistry. Thus, it prompted us to develop the preparation of highly valuable alkoxyamines via ionic chemistry and the radical cyclization was triggered by thermal initiation. Following that procedure, bicyclic, spiro and eight-membered lactones were easily prepared in good yields with very high stereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.100
• 作为产物：
  描述：

  methyl 2-(N-tert-butyl-N-(1-diethylphosphono-2,2-dimethylpropyl)aminooxy)propionate 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以90%的产率得到2-[N-tert-butyl-N-(1-diethoxyphosphoryl-2,2-dimethylpropyl)aminoxy]propionic acid
  参考文献：
  名称：

  Alkoxyamines derived from beta-phosphorylated nitroxides, and use thereof for preparing polymerized or non-polymerized mono-or polyalkoxyamines

  摘要：

  该发明涉及使用式(I)的烷氧胺来制备式(II)的聚合或非聚合的单烷氧胺或多烷氧胺。

  公开号：

  US20050065119A1

文献信息

• Simple Synthesis of Cladribine-Based Anticancer Polymer Prodrug Nanoparticles with Tunable Drug Delivery Properties
  作者：Yinyin Bao、Tanguy Boissenot、Elise Guégain、Didier Desmaële、Simona Mura、Patrick Couvreur、Julien Nicolas

  DOI：10.1021/acs.chemmater.6b02502

  日期：2016.9.13

  prodrugs based on cladribine (CdA) as an anticancer drug have been prepared by growing short, well-defined polyisoprene (PI) chains (with number-average molar mass = 1420–4980 g mol–1 and dispersity = 1.09–1.20) from CdA-bearing alkoxyamine by nitroxide-mediated polymerization. Nanoparticles were formed by nanoprecipitation into water of the resulting CdA-PI conjugates and exhibited long-term colloidal stability

  基于克拉屈滨（CdA）作为抗癌药的聚合物前药是通过以下方法制备的：从短的，定义明确的聚异戊二烯（PI）链（数均摩尔质量= 1420–4980 g mol –1，分散度= 1.09–1.20）含CdA的烷氧基胺通过硝基氧介导的聚合反应。纳米粒子是通过将所生成的CdA-PI共轭物纳米沉淀到水中而形成的，并且只需调节药物/聚合物接头，聚合物，就可以在不同介质中表现出长期的胶体稳定性，可调节的胶体特性，药物释放曲线和体外抗癌活性。链长和配方参数。重复静脉注射后未观察到对小鼠的明显体内毒性。
• Long-range polar and steric effects in propionate-SG1-type alkoxyamines (SG1-CHMeCOOX): a multiparameter analysis
  作者：Gennady Ananchenko、Emmanuel Beaudoin、Denis Bertin、Didier Gigmes、Pierre Lagarde、Sylvain R. A. Marque、Eve Revalor、Paul Tordo

  DOI：10.1002/poc.1035

  日期：2006.4

  The effects of the substituent X on the homolysis rate constants (kd) of SG1-propionate type alkoxyamines (SG1-CHMeCOOX) are analyzed by a multiparametric equation with υ, the steric constant and σI, the polar inductive/field Hammett constant of X. An influence of long-range polar and steric effects on kd was observed, that is, decrease in kd with increasing size of the X group and increase in kd with

  在均裂速率常数（取代基X的效果ķ d SG1-丙酸型烷氧基胺（SG1-CHMeCOOX）的）通过用多参数方程分析υ，空间常数和σ我，的极性的感应/场哈米特常数长范围上的极性和空间效应的X的影响ķ d观察到，即，减少在ķ d与在增加X基团和增加的尺寸ķ d随X基团的极性。版权所有©2006 John Wiley＆Sons，Ltd.
• Long-Range Polar Effect on the C-ON Bond Homolysis in (tert-Butyl[1-(diethylphosphonyl)-2,2-dimethylpropyl]aminoxyl) SG1-Based Alkoxyamines
  作者：Denis Bertin、Didier Gigmes、Sylvain R. A. Marque、Stephan Milardo、Jérôme Peri、Paul Tordo

  DOI：10.1135/cccc20042223

  日期：——

  Alkoxyamines and persistent nitroxyl radicals are important regulators of nitroxide-mediated radical polymerization. Because the polymerization times decrease with the increasing rate constant of the homolysis of the C-ON bond between the polymer chain and the nitroxyl moiety, the factors influencing the cleavage rate constant are of considerable interest. Because alkyl acrylate monomers are among the most used in polymerization, we present the measures of the rate constants (k_d) of the C-ON bond cleavage for new SG1 based alkoxyamine models containing para-substituted aromatic acrylates (4-XC₆H₄OC(O)C(Me)H-SG1). It appears that the values of k_d increase with the electron-withdrawing properties of the para-substituent groups (4-X) of the ester SG1-based alkoxyamines.

  烷氧胺和持久的亚硝基自由基是亚硝基介导的自由基聚合的重要调节剂。由于聚合时间随着聚合物链和亚硝基部分之间的C-ON键的断裂速率常数的增加而减少，因此影响断裂速率常数的因素具有相当大的兴趣。由于烷基丙烯酸酯单体是聚合中最常用的单体之一，我们提出了基于新的SG1烷氧胺模型的包含对位取代芳香丙烯酸酯（4-XC6H4OC(O)C(Me)H-SG1）的C-ON键断裂速率常数（kd）的测量值。看来，对SG1基烷氧胺的酯类的4-X对位取代基团的电子吸引性质（4-X）的kd值随之增加。
• Nanoparticles with In Vivo Anticancer Activity from Polymer Prodrug Amphiphiles Prepared by Living Radical Polymerization
  作者：Simon Harrisson、Julien Nicolas、Andrei Maksimenko、Duc Trung Bui、Julie Mougin、Patrick Couvreur

  DOI：10.1002/anie.201207297

  日期：2013.2.4

  bullets: Novel anticancer nanoparticles made of well‐defined polymer–drug conjugate amphiphiles are prepared by the controlled growth of a hydrophobic polyisoprene chain from a drug macroinitiator by using nitroxide‐mediated polymerization (NMP; see picture). The resulting conjugates self‐assembled into nanoparticles exhibiting high drug payloads and significant anticancer activities both in vitro and

  神奇的橡皮子弹：由定义明确的聚合物-药物共轭两亲物制成的新型抗癌纳米粒子是通过使用氮氧介导的聚合（NMP；见图）从药物大分子引发剂中受控生长疏水性聚异戊二烯链来制备的。由此产生的缀合物自组装成纳米颗粒，在体外和体内表现出高药物负载和显着的抗癌活性。
• Fluorescent polymer prodrug nanoparticles with aggregation-induced emission (AIE) properties from nitroxide-mediated polymerization
  作者：Yinyin Bao、Elise Guégain、Valérie Nicolas、Julien Nicolas

  DOI：10.1039/c6cc09052d

  日期：——

  Aggregation-induced emission (AIE)-active polymer prodrug nanoparticles were readily prepared by growing short, well-defined polymer chains from an AIE dye by nitroxide-mediated polymerization, followed by co-nanoprecipitation of the resulting conjugates with similarly constructed anticancer polymer prodrugs. The nanoparticles had sharp fluorescence signal offering excellent imaging ability in living

  聚集诱导发射（AIE）-活性聚合物前体药物纳米颗粒的制备很容易，方法是通过氮氧化物介导的聚合反应从AIE染料中生长出清晰明确的短聚合物链，然后将所得的偶联物与类似构建的抗癌聚合物前体药物共纳米沉淀。纳米粒子具有清晰的荧光信号，可在活细胞中提供出色的成像能力，并且可以精确监控其细胞内定位。