2-Cyanoethoxy(diisopropylamino)-2-(methacryloyloxy)ethoxyphosphine | 190070-80-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Cyanoethoxy(diisopropylamino)-2-(methacryloyloxy)ethoxyphosphine
• 英文别名: 2-((2-cyanoethoxy)(diisopropylamino)phosphinoxy)ethyl methacrylate；2-[2-Cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyethyl 2-methylprop-2-enoate
• CAS: 190070-80-5
• 化学式: C₁₅H₂₇N₂O₄P
• 分子量: 330.364
• InChiKey: LVBOXFDZMHXGJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Cyanoethoxy(diisopropylamino)-2-(methacryloyloxy)ethoxyphosphine 在 4,5-二氯咪唑 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 40.17h， 生成 2-甲基丙烯酰氧乙基磷酸胆碱
  参考文献：
  名称：

  Preparation of phospholipid analogues using the phosphoramidite route

  摘要：

  磷酸胺酯路线已被用于制备具有生物相容性特性的磷脂类类似物，以及用于制备生物相容性聚合物的单体2-(甲基丙烯酰氧基)乙基磷酰胆碱。对已有方法的改进包括，作为热不稳定的四唑的替代品，使用4,5-二氯咪唑作为酸催化剂，以从相应的磷酸胺酯制备磷酸酯，并使用氧化三甲胺作为氧化剂，将磷酸酯转化为相应的磷酸盐。

  DOI：

  10.1039/a910270l
• 作为产物：
  描述：

  甲基丙烯酸羟乙酯 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-Cyanoethoxy(diisopropylamino)-2-(methacryloyloxy)ethoxyphosphine
  参考文献：
  名称：

  Preparation of phospholipid analogues using the phosphoramidite route

  摘要：

  磷酸胺酯路线已被用于制备具有生物相容性特性的磷脂类类似物，以及用于制备生物相容性聚合物的单体2-(甲基丙烯酰氧基)乙基磷酰胆碱。对已有方法的改进包括，作为热不稳定的四唑的替代品，使用4,5-二氯咪唑作为酸催化剂，以从相应的磷酸胺酯制备磷酸酯，并使用氧化三甲胺作为氧化剂，将磷酸酯转化为相应的磷酸盐。

  DOI：

  10.1039/a910270l

文献信息

• Polymer, contrast agent for nuclear magnetic resonance analysis or magnetic resonance imaging using the polymer, compound and method of nuclear magnetic resonance analysis and method of magnetic resonance imaging using the polymer
  申请人：CANON KABUSHIKI KAISHA

  公开号：US10029021B2

  公开（公告）日：2018-07-24

  As a substance used as a contrast agent for a method of nuclear magnetic resonance analysis or a method of magnetic resonance imaging, a substance with high selectivity and high sensitivity was demanded. According to the present invention, when a polymer having, in a side chain thereof, a sequence of a 1H—13C—15N, 1H—15N—13C or 1H—13C—13C bond, that is, a structure labeled with stable isotopes of 13C and 15N, is used, the abundance of such a sequence in one molecule can be increased, and hence, high selectivity and higher sensitivity can be attained when used as a contrast agent.

  作为核磁共振分析方法或磁共振成像方法中用作对比剂的物质，需要一种具有高选择性和高灵敏度的物质。根据本发明，当使用在其侧链中具有 1H-13C-15N、1H-15N-13C 或 1H-13C-13C 键序列（即用 13C 和 15N 的稳定同位素标记的结构）的聚合物时，可以增加这种序列在一个分子中的丰度，因此在用作造影剂时可以获得高选择性和高灵敏度。
• Magnetic Resonance Imaging of Tumor with a Self-Traceable Phosphorylcholine Polymer
  作者：Hisatsugu Yamada、Yoshinori Hasegawa、Hirohiko Imai、Yuki Takayama、Fuminori Sugihara、Tetsuya Matsuda、Hidehito Tochio、Masahiro Shirakawa、Shinsuke Sando、Yu Kimura、Akio Toshimitsu、Yasuhiro Aoyama、Teruyuki Kondo

  DOI：10.1021/ja510479v

  日期：2015.1.21

  Polymers are concentration-amplified with respect to the monomeric units. We show here that a phosphorylcholine polymer enriched with C-13/N-15 at the methyl groups is self-traceable by multiple-resonance (heteronuclear-correlation) NMR in tumor-bearing mice inoculated with the mouse rectal cancer cell line (colon 26). Preliminary measurements indicated that the present polymeric nanoprobe was satisfactorily distinguished from lipids and detectable with far sub-micromolar spectroscopic and far sub-millimolar imaging sensitivities. Detailed ex vivo and in vivo studies for the tumor-bearing mice administered the probe with a mean molecular weight of 63 000 and a mean size of 13 nm, revealed the following: (1) this probe accumulates in the tumor highly selectively (besides renal excretion) and efficiently (up to 30% of the injected dose), (2) the tumor can thus be clearly in vivo imaged, the lowest clearly imageable dose of the probe being 100 mg/kg or 2.0 mg/20-g mouse, and (3) the competition between renal excretion and tumor accumulation is size-controlled; that is, the larger (higher molecular-weight) and smaller (lower molecular-weight) portions of the probe undergo tumor accumulation and renal excretion, respectively. The observed size dependence suggests that the efficient tumor-targeting of the present probe is stimulated primarily by the so-called enhanced permeability and retention (EPR) effect, that is, size-allowed invasion of the probe into the tumor tissue via defective vascular wall. Self-traceable polymers thus open an important area of magnetic resonance imaging (MRI) of tumors and may provide a highly potential tool to visualize various delivery/localization processes using synthetic polymers.
• POLYMER, CONTRAST AGENT FOR NUCLEAR MAGNETIC RESONANCE ANALYSIS OR MAGNETIC RESONANCE IMAGING USING THE POLYMER, COMPOUND AND METHOD OF NUCLEAR MAGNETIC RESONANCE ANALYSIS AND METHOD OF MAGNETIC RESONANCE IMAGING USING THE POLYMER
  申请人：CANON KABUSHIKI KAISHA

  公开号：US20150071861A1

  公开（公告）日：2015-03-12

  As a substance used as a contrast agent for a method of nuclear magnetic resonance analysis or a method of magnetic resonance imaging, a substance with high selectivity and high sensitivity was demanded. According to the present invention, when a polymer having, in a side chain thereof, a sequence of a 1 H— 13 C— 15 N, 1 H— 15 N— 13 C or 1 H— 13 C— 13 C bond, that is, a structure labeled with stable isotopes of 13 C and 15 N, is used, the abundance of such a sequence in one molecule can be increased, and hence, high selectivity and higher sensitivity can be attained when used as a contrast agent.
• Preparation of phospholipid analogues using the phosphoramidite route
  作者：Judith E. Browne、Michael J. Driver、Jeremy C. Russell、Peter G. Sammes

  DOI：10.1039/a910270l

  日期：——

  The phosphoramidite route has been used to prepare phospholipid analogues possessing biocompatible properties and the monomer 2-(methacryloyloxy)ethylphosphorylcholine, utilised in the preparation of biocompatible polymers. Modifications to established methodology include, as an alternative to the thermally unstable tetrazole, the use of 4,5-dichloroimidazole as an acid catalyst for preparing phosphite esters from the corresponding phosphoramidites, and the use of trimethylamine N-oxide as oxidant for the conversion of the phosphite esters into the corresponding phosphates.

  磷酸胺酯路线已被用于制备具有生物相容性特性的磷脂类类似物，以及用于制备生物相容性聚合物的单体2-(甲基丙烯酰氧基)乙基磷酰胆碱。对已有方法的改进包括，作为热不稳定的四唑的替代品，使用4,5-二氯咪唑作为酸催化剂，以从相应的磷酸胺酯制备磷酸酯，并使用氧化三甲胺作为氧化剂，将磷酸酯转化为相应的磷酸盐。