oleyl tetradecyl H-phosphonate | 1042667-58-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: oleyl tetradecyl H-phosphonate
• 英文别名: (Z)-1-[oxido(tetradecoxy)phosphaniumyl]oxyoctadec-9-ene
• CAS: 1042667-58-2
• 化学式: C₃₂H₆₅O₃P
• 分子量: 528.84
• InChiKey: MGWAKXKGUKAQEM-ZCXUNETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  36
• 可旋转键数：
  31
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  41.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吡啶 、 oleyl tetradecyl H-phosphonate 在 三苯基氯甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 6.0h， 生成 C₃₇H₆₈NO₃P
  参考文献：
  名称：

  Synthesis and evaluation of new phosphonolipid compounds for gene delivery

  摘要：

  The preparation of a series of novel water soluble cationic lipid derivatives possessing phosphonate ester groups linked to the para-position of N-methyl pyridinium moieties and bearing either identical or different alkyl chains is reported. The obtained phospholipids were tested for transfection efficiency into three different mammalian cell lines alone and in conjunction with diphytanoylphosphatidylethanolamine (DiPPE) or dioleylphosphatidylethanolamine (DOPE), using an assay adapted for 96-well microplates based on the detection of a colorimetric change caused by the production of a chromogen induced by expressed secreted human placental alkaline phosphatase. In our conditions, the highest transfection activities of cells HEK293 and hard-to-transfect cell lines B 16 and CHO were achieved with a 4-phosphonobutylpyridinium compound used at 1:5, 1: 10 or 3:6 DNA/lipid ratio bearing two myristyl chains in the presence of the fusogenic helper lipid DiPPE. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.11.002
• 作为产物：
  描述：

  十四醇 、 C₂₄H₄₁O₃P 在 吡啶 作用下， 反应 3.0h， 生成 oleyl tetradecyl H-phosphonate
  参考文献：
  名称：

  Synthesis and evaluation of new phosphonolipid compounds for gene delivery

  摘要：

  The preparation of a series of novel water soluble cationic lipid derivatives possessing phosphonate ester groups linked to the para-position of N-methyl pyridinium moieties and bearing either identical or different alkyl chains is reported. The obtained phospholipids were tested for transfection efficiency into three different mammalian cell lines alone and in conjunction with diphytanoylphosphatidylethanolamine (DiPPE) or dioleylphosphatidylethanolamine (DOPE), using an assay adapted for 96-well microplates based on the detection of a colorimetric change caused by the production of a chromogen induced by expressed secreted human placental alkaline phosphatase. In our conditions, the highest transfection activities of cells HEK293 and hard-to-transfect cell lines B 16 and CHO were achieved with a 4-phosphonobutylpyridinium compound used at 1:5, 1: 10 or 3:6 DNA/lipid ratio bearing two myristyl chains in the presence of the fusogenic helper lipid DiPPE. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.11.002

文献信息

• Convenient Method for the Preparation of Heterodialkyl‐<i>H</i>‐phosphonates from Diphenyl‐<i>H</i>‐phosphonate
  作者：Angélique Durand Dal‐Maso、Frédéric Legendre、Casimir Blonski、Pascal Hoffmann

  DOI：10.1080/00397910801982282

  日期：2008.5

  Abstract A procedure for the introduction of two different alkyl chains (myristyl, oleyl and phytanyl) leading to heterodialkyl‐H‐phosphonates is reported, based on two successive transesterification reactions of commercially available diphenyl‐H‐phosphonate with the corresponding alcohols.

  摘要 基于市售的二苯基-H-膦酸酯与相应醇的两次连续酯交换反应，报道了引入两种不同的烷基链（肉豆蔻基、油基和植烷基）导致杂二烷基-H-膦酸酯的程序。