1-pentadecanyl dichlorophosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-pentadecanyl dichlorophosphate
• 英文别名: Pentadecyl Phosphorodichloridate；1-dichlorophosphoryloxypentadecane
• 化学式: C₁₅H₃₁Cl₂O₂P
• 分子量: 345.29
• InChiKey: GHTACXFJOAGPEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-pentadecanyl dichlorophosphate 、 三乙胺 在 二乙氨基乙醇 作用下， 反应 3.0h， 生成 pentadecanyltriethylammonium chloride
  参考文献：
  名称：

  从正醇和烯丙醇一锅法合成阳离子两亲物

  摘要：

  已经开发出一种新型、高效的单锅法，首次以良好的收率从正醇和天然萜烯（烯丙醇）合成两亲化合物，如 N-烷基化/N-烯丙基化三乙胺和吡啶鎓盐。这些两亲物已作为表面活性剂、DNA 载体和其他生物应用获得工业应用。研究了 N-烷基化和 N-烯丙基化三乙胺和吡啶盐的 DNA 递送功效和细胞毒性。

  DOI：

  10.1055/s-0030-1260939
• 作为产物：
  描述：

  1-十五醇 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-pentadecanyl dichlorophosphate
  参考文献：
  名称：

  Salinipostin A的首次对映选择性合成，Salinipostin A是从Salinispora sp中分离出来的海洋环状烯醇-磷酸三酯

  摘要：

  Salinipostins是从海洋来源的Salinispora sp。分离得到的环状烯醇磷酸三酯。作为抗疟化合物。在此，实现了对salinipostin A的首次对映选择性合成。有机催化剂介导的不对称环丙烷化和区域选择性环丙烷开环是关键步骤。

  DOI：

  10.1016/j.tetlet.2019.07.008

文献信息

• Synthesis of structural analogues of hexadecylphosphocholine and their antineoplastic, antimicrobial and amoebicidal activity
  作者：Lukáš Timko、Eva Fischer-Fodor、Mária Garajová、Martin Mrva、Gabriela Chereches、František Ondriska、Marián Bukovský、Miloš Lukáč、Janka Karlovská、Janka Kubincová、Ferdinand Devínsky

  DOI：10.1016/j.ejmech.2015.02.014

  日期：2015.3

  Twelve derivatives of hexadecylphosphocholine (miltefosine) were synthesized to determine how the position and length of the alkyl chain within the molecule influence their biological activities. The prepared alkylphosphocholines have the same molecular formula as miltefosine. Activity of the compounds was studied against a spectrum of tumour cells, two species of protozoans, bacteria and yeast. Antitumour efficacy of some alkylphosphocholines measured up on MCF-7, A2780, HUT-78 and THP-1 cell lines was higher than that of miltefosine. The compounds showed antiprotozoal activity against Acanthamoeba lugdunensis and Acanthamoeba quina. Some of them also possess fungicidal activity against Candida albicans equal to miltefosine. No antibacterial activity was observed against Staphylococcus aureus and Escherichia coil. A difference in position of a long hydrocarbon chain within the structure with maximum efficacy was observed for antitumour, antiprotozoal and antifungal activity. (C) 2015 Elsevier Masson SAS. All rights reserved.
• One-Pot Synthesis of Cationic Amphiphiles from n-Alcohols and Allyl Alcohols
  作者：Tadigoppula Narender、R. Tripathi、Gaurav Madhur、K. Reddy、S. Sarkar、J. Sarkar

  DOI：10.1055/s-0030-1260939

  日期：2011.7

  one-pot method has been developed to synthesize amphiphiles such as N-alkylated/N-allylated triethyl-amines and pyridinium salts for the first time from n-alcohols and naturally occurring terpenes (allyl alcohols) in good yields. These amphiphiles have got industrial application as surfactants, DNA carriers, and other biological applications. The DNA delivery efficacy and cytotoxicity of N-alkylated and

  已经开发出一种新型、高效的单锅法，首次以良好的收率从正醇和天然萜烯（烯丙醇）合成两亲化合物，如 N-烷基化/N-烯丙基化三乙胺和吡啶鎓盐。这些两亲物已作为表面活性剂、DNA 载体和其他生物应用获得工业应用。研究了 N-烷基化和 N-烯丙基化三乙胺和吡啶盐的 DNA 递送功效和细胞毒性。
• First enantioselective synthesis of salinipostin A, a marine cyclic enol-phosphotriester isolated from Salinispora sp
  作者：Hironori Okamura、Takanobu Fujioka、Naoki Mori、Tohru Taniguchi、Kenji Monde、Hidenori Watanabe、Hirosato Takikawa

  DOI：10.1016/j.tetlet.2019.07.008

  日期：2019.8

  Salinipostins are cyclic enol-phosphotriesters isolated from a marine-derived Salinispora sp. as antimalarial compounds. Herein, the first enantioselective synthesis of salinipostin A was achieved. Organocatalyst-mediated asymmetric cyclopropanation and regioselective cyclopropane ring opening were the key steps.

  Salinipostins是从海洋来源的Salinispora sp。分离得到的环状烯醇磷酸三酯。作为抗疟化合物。在此，实现了对salinipostin A的首次对映选择性合成。有机催化剂介导的不对称环丙烷化和区域选择性环丙烷开环是关键步骤。