1-tetradecylphosphorodichloridate | 109259-35-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 1-tetradecylphosphorodichloridate
• 英文别名: Tetradecyl phosphorodichloridate；1-dichlorophosphoryloxytetradecane
• CAS: 109259-35-0
• 化学式: C₁₄H₂₉Cl₂O₂P
• 分子量: 331.263
• InChiKey: CWLGNBMUGORIIO-UHFFFAOYSA-N

物化性质

• 沸点：
  390.6±11.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  19
• 可旋转键数：
  14
• 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-tetradecylphosphorodichloridate 在 copper(l) iodide 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 20.0h， 生成 3-[4-({[6-hydroxyspiro(phthalid-3,9-xanthen-3-yl)]oxy}methyl)-1H-1,2,3-triazol-1-yl]propyl tetradecyl 2-(dimethylamino)ethylamidophosphate
  参考文献：
  名称：

  功能化磷脂分子平台：用于生产阳离子荧光脂质

  摘要：

  荧光两亲性磷脂（中性或阳离子），其中荧光探针包含在脂质域中，是通过具有两个不同脂质链的磷酰胺中间体合成的。这些脂质链之一用叠氮化物或炔烃基团进行 ω 功能化，随后通过 Huisgen 环加成作用引入荧光探针。本研究考虑了五种不同的荧光探针（萘二甲酰亚胺、丹磺酰、荧光素、尼罗红和香豆素）。这些中性和阳离子荧光脂质与选定的阳离子脂质 (KLN47) 以 1% 的摩尔比加入，以产生通过动态光散射和 zeta 电位测量表征的脂质体溶液。

  DOI：

  10.1002/ejoc.201301416
• 作为产物：
  描述：

  十四醇 在 三乙胺 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 1-tetradecylphosphorodichloridate
  参考文献：
  名称：

  米替福新类似物的合成和抗真菌活性

  摘要：

  Miltefosine 是一种烷基磷酸胆碱，在体外具有广谱抗真菌活性，在隐球菌病小鼠模型中的体内疗效有限。为了进一步探索此类化合物治疗全身性真菌病的潜力，通过修饰米替福新的胆碱结构部分和烷基链长度，合成了九种类似物 ( 3a - 3i )。这些化合物对机会性真菌病原体白色念珠菌、光滑念珠菌、克柔念珠菌、烟曲霉和新型隐球菌的体外测试表明，N-苄基-N、N-二甲基-2-{[(十六烷氧基)羟基膦基]氧基}乙胺内盐（3a )，N，N-二甲基-N- (4-硝基苄基)-2-{[(十六烷氧基)羟基膦基]氧基}乙胺内盐( 3d )，和N- (4-甲氧基苄基) -N，N-二甲基-与 MIC 为 2.5-3.3 μg/mL 的米替福新相比，2-{[(十六烷氧基)羟基膦基]氧基}乙胺内盐 ( 3e ) 对所有测试病原体的最小抑制浓度 (MIC) 为 2.5-5.0 μg/mL。化合物3a对三种类似于米替福新的哺

  DOI：

  10.1016/j.bmcl.2013.06.096

文献信息

• Cationic lipophosphoramidates with two different lipid chains: synthesis and evaluation as gene carriers
  作者：Stéphanie S. Le Corre、Mathieu Berchel、Nawal Belmadi、Caroline Denis、Jean-Pierre Haelters、Tony Le Gall、Pierre Lehn、Tristan Montier、Paul-Alain Jaffrès

  DOI：10.1039/c3ob42270d

  日期：——

  The synthesis of a series of new cationic lipids possessing two different lipid chains is detailed. The transfection efficacies have shown the interest to associate a phytanyl chain with either, a lauryl or oleyl chain.

  一系列新的阳离子脂质合成细节涉及具有两种不同脂肪链的脂质。转染效率表明将一种萜烯基链与月桂基链或油酸基链结合是有趣的。
• Synthesis and biological activity of dialkylphosphocholines
  作者：Miloš Lukáč、Martin Mrva、Eva Fischer-Fodor、Ivan Lacko、Marián Bukovský、Natalia Miklášová、František Ondriska、Ferdinand Devínsky

  DOI：10.1016/j.bmcl.2009.09.079

  日期：2009.11

  A series of dialkylphosphocholines were prepared and evaluated for their biological activity. The antiprotozoal activity was determined against Acanthamoeba lugdunensis. Compound 15 exhibited excellent trophocidal activity. None of the tested dialkylphosphocholines exhibited better fungicidal activity against Candida albicans than miltefosine. The antineoplastic activity was determined against HeLa. The most cytotoxic was compound 10, which was more active against tumor cells as against normal cells. (C) 2009 Elsevier Ltd. All rights reserved.
• Autotaxin structure–activity relationships revealed through lysophosphatidylcholine analogs
  作者：E. Jeffrey North、Daniel A. Osborne、Peter K. Bridson、Daniel L. Baker、Abby L. Parrill

  DOI：10.1016/j.bmc.2009.03.030

  日期：2009.5

  Autotaxin (ATX) catalyzes the hydrolysis of lysophosphatidylcholine (LPC) to form the bioactive lipid lysophosphatidic acid (LPA). LPA stimulates cell proliferation, cell survival, and cell migration and is involved in obesity, rheumatoid arthritis, neuropathic pain, atherosclerosis and various cancers, suggesting that ATX inhibitors have broad therapeutic potential. Product feedback inhibition of ATX by LPA has stimulated structure-activity studies focused on LPA analogs. However, LPA displays mixed mode inhibition, indicating that it can bind to both the enzyme and the enzyme-substrate complex. This suggests that LPA may not interact solely with the catalytic site. In this report we have prepared LPC analogs to help map out substrate structure-activity relationships. The structural variances include length and unsaturation of the fatty tail, choline and polar linker presence, acyl versus ether linkage of the hydrocarbon chain, and methylene and nitrogen replacement of the choline oxygen. All LPC analogs were assayed in competition with the synthetic substrate, FS-3, to show the preference ATX has for each alteration. Choline presence and methylene replacement of the choline oxygen were detrimental to ATX recognition. These findings provide insights into the structure of the enzyme in the vicinity of the catalytic site as well as suggesting that ATX produces rate enhancement, at least in part, by substrate destabilization. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.
• Practical Synthesis of 3-Carboxy-(2<i>R</i>)- [[hydroxy[(tetradecyl)oxy]phosphinyl]oxy]-<i>N</i>,<i>N</i>,<i>N</i>-trimethyl-1-propanaminium Hydroxide Inner Salt (CPI975):  A Carnitine Palmitoyltransferase I Inhibitor
  作者：Mahavir Prashad、John C. Amedio、Lech Ciszewski、George Lee、Carmine Villa、Kau-Ming Chen、Kapa Prasad、Oljan Repič

  DOI：10.1021/op020215o

  日期：2002.11.1

  An efficient, safe, and cost-effective synthesis of 3-carboxy-(2R)[[hydroxy[(tetradecyl)oxy]phosphinyl]oxy]-N,N,N-trimethyl-1-propanaminium hydroxide inner salt (1, CPI975), a carnitine palmitoyltransferase I inhibitor, is described. The reaction of 1-tetradecanol (2) with stoichiometric amounts Of PCl3 in THF at -15 to -20 degreesC furnished 1-tetradecyl phosphorochloridate (3). Treatment of 3 directly with L-carnitine (7) in THF in the presence of 2,4,6.collidine afforded 8, which was oxidized with bromine to afford a crude aqueous solution of 1. Desalting was done using a cheap, stable, and recyclable resin Amberlite XAD-4. The drug substance was purified by recrystallization from a mixture of ethanol and THE The yield of 1 was 65 % with 99.7% purity. Alternatively, instead of desalting with Amberlite XAD-4 resin, 1 can be isolated by an extraction with 1-decanol, followed by precipitation with acetone and recrystallization from ethanol and THF mixture.