2-((12-iodododecyl)oxy)tetrahydro-2H-pyran | 55833-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-((12-iodododecyl)oxy)tetrahydro-2H-pyran
• 英文别名: 2-(12-iodododecyl-1-oxy)tetrahydropyran；2-(12-iodododecyl-2-oxy)tetrahydropyran；2-[(12-Iodododecyl)oxy]oxane；2-(12-iodododecoxy)oxane
• CAS: 55833-20-0
• 化学式: C₁₇H₃₃IO₂
• 分子量: 396.352
• InChiKey: JGALVYNWOOPRQR-UHFFFAOYSA-N

物化性质

• 沸点：
  420.0±30.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((12-iodododecyl)oxy)tetrahydro-2H-pyran 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 32.67h， 生成 2-(tetradec-13-yn-1-yloxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  受古细菌启发的四醚脂质体中药物包封和保留的表征†

  摘要：

  小分子跨膜的被动泄漏是脂质体药物制剂的主要限制。在这里，我们评估了封装在脂质体中的3种临床使用的化学治疗剂（阿糖胞苷，甲氨蝶呤和长春新碱）的泄漏情况，这些脂质体由合成的，古细菌启发的，跨膜的四醚脂质组成。与由市售二酰基脂质形成的脂质体相比，由纯四醚脂质组成的脂质体对中性和带正电荷的药物均表现出优异的保留率（药物泄漏速率最多降低约9倍）。一种带负电荷的药物，没有从任何一种脂质体中泄漏出来。我们还证明了由古细菌启发的脂质制成的脂质体可用于将包封的小分子递送到活细胞中。

  DOI：

  10.1039/c6ob02832b
• 作为产物：
  描述：

  12-(四氢吡喃-2'-氧基)十二烷-1-醇 在 吡啶 、 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 2-((12-iodododecyl)oxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Z-Selective intramolecular Horner–Wadsworth–Emmons reaction for the synthesis of macrocyclic alkenes

  摘要：

  The Z-selective intramolecular Horner-Wadsworth-Emmons reaction of the substrates 7-12 (RO)(2)P(O)CHR'CO(2)Et (R' = (CH(2))(n)CHO) (R = Ph or o-tBuC(6)H(4)) gives the 13-18-membered cyclic alkenes selectively (up to Z:E = 97:3) in good yields using NaH in THF under high dilution conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.043

文献信息

• A dialkynoyl analogue of DOPE improves gene transfer of lower-charged, cationic lipoplexes
  作者：Steven Fletcher、Ayesha Ahmad、Eric Perouzel、Michael R. Jorgensen、Andrew D. Miller

  DOI：10.1039/b514532e

  日期：——

  Positively-charged gene delivery agents, such as cationic liposomes, typically prepared by mixing a cationic lipid and a neutral lipid in a 1 : 1 molar ratio, exhibit a fundamental flaw: on the one hand, the charge encourages cell uptake; on the other hand, the charge leads to aggregation in vivo with anionic serum components. We herein report a more phase-stable analogue of the zwitterionic and fusogenic lipid DOPE that allows for the reduction of the cationic lipid component of the liposome from 50 to 9 mol% with almost no apparent loss in transfection activity. This reduction in charge may induce important in vivo stability whilst still imparting high cell uptake and transgene expression.

  带正电荷的基因递送载体，如阳离子脂质体，通常通过将阳离子脂质和中性脂质以1:1的摩尔比例混合制备，存在一个根本性缺陷：一方面，正电荷促进细胞摄取；另一方面，正电荷导致其在体内与带负电的血清成分发生聚集。本文报道了一种更相稳定的两性离子且具有融合性的脂质DOPE的类似物，能够在几乎不明显降低转染活性的情况下，将脂质体中的阳离子脂质成分从50%降低到9%。这种电荷的减少可能增加体内稳定性，同时仍保持高细胞摄取率和转基因表达。
• Activated carboxylates from the photooxygenation of oxazoles. Application to the synthesis of recifeiolide and other macrocyclic lactones.
  作者：Harry H. Hassennan、Ronald J. Gambale、Mitchell J. Pulwer

  DOI：10.1016/s0040-4039(01)90426-5

  日期：1981.1

  The oxazole system may serve as a protecting group for the carboxyl function. The carboxylate is generated under the mild conditions of photooxygenation in high yield in the form of the reactive triamide. This reaction has been applied to the synthesis of macrocyclic lactones.

  恶唑体系可以用作羧基官能团的保护基。羧酸盐是在温和的光氧化条件下以反应性三酰胺的形式高收率地生成的。该反应已应用于大环内酯的合成。
• In Vivo Studies of Dialkynoyl Analogues of DOTAP Demonstrate Improved Gene Transfer Efficiency of Cationic Liposomes in Mouse Lung
  作者：Steven Fletcher、Ayesha Ahmad、Eric Perouzel、Andrew Heron、Andrew D. Miller、Michael R. Jorgensen

  DOI：10.1021/jm0507227

  日期：2006.1.1

  A novel set of dialkynoyl analogues of the cationic, gene delivery lipid DOTAP (1) was synthesized. Structure-activity studies demonstrate that replacement of the cis-double bonds of DOTAP with triple bonds in varying positions alters both the physical properties of the resultant cationic liposome-DNA complexes and their biological functionalities, both in vitro and in vivo. Particularly, in vivo studies demonstrate that pDNA transfection of mouse lung endothelial cells with lead analogue DS(14-yne)TAP (4):cholesterol lipoplexes exhibits double the transfection level with less associated toxicity relative to the well-established DOTAP:cholesterol system. In fact, 4:cholesterol delivers up to 3 times the dose of pDNA in mice than can be tolerated by DOTAP, leading to nearly 3 times greater marker-gene expression. X-ray diffraction studies suggest that lipoplexes containing analogue 4 display increased stability at physiological temperatures. Our results thus suggest that analogue 4 is a potentially strong candidate for the gene therapy of lung tumors.
• Z-Selective intramolecular Horner–Wadsworth–Emmons reaction for the synthesis of macrocyclic alkenes
  作者：Kaori Ando、Kaori Sato

  DOI：10.1016/j.tetlet.2011.01.043

  日期：2011.3

  The Z-selective intramolecular Horner-Wadsworth-Emmons reaction of the substrates 7-12 (RO)(2)P(O)CHR'CO(2)Et (R' = (CH(2))(n)CHO) (R = Ph or o-tBuC(6)H(4)) gives the 13-18-membered cyclic alkenes selectively (up to Z:E = 97:3) in good yields using NaH in THF under high dilution conditions. (C) 2011 Elsevier Ltd. All rights reserved.
• Ando, Tetsu; Ogura, Yasushi; Uchiyama, Masaaki, Agricultural and Biological Chemistry, 1988, vol. 52, # 6, p. 1415 - 1424
  作者：Ando, Tetsu、Ogura, Yasushi、Uchiyama, Masaaki

  DOI：——

  日期：——