2-溴乙基二氯膦酸酯 | 4167-02-6

• 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
• 中文名称: 2-溴乙基二氯膦酸酯
• 中文别名: Β-溴乙基磷酰二氯；2-溴乙基磷酰二氯
• 英文名称: 2-Bromoethyl dichlorophosphate
• 英文别名: 2-bromoethylphosphoric acid dichloride；1-bromo-2-dichlorophosphoryloxyethane
• CAS: 4167-02-6
• 化学式: C₂H₄BrCl₂O₂P
• mdl: MFCD04116122
• 分子量: 241.836
• InChiKey: NYKRTKYIPKOPLK-UHFFFAOYSA-N

物化性质

• 沸点：
  75-78°C
• 溶解度：
  氯仿、DMSO（少量溶解）、乙酸乙酯（少量溶解）

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  3
• 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

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  2-溴乙基二氯膦酸酯 生成 3-(dodecyloxy)-2-hydroxypropyl 2-(trimethylammonio)ethyl phosphate
  参考文献：
  名称：

  GODFROID J. -J.; BROQUET C.; JOUQUEY S.; LEBBAR M.; HEYMANS F.; REDEUILH +, J. MED. CHEM., 30,(1987) N 5, 5

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴乙醇 在 三氯氧磷 作用下， 以 甲苯 为溶剂， 生成 2-溴乙基二氯膦酸酯
  参考文献：
  名称：

  古细菌双极脂质类似物的合成：多功能药物/基因传递系统的一种方法。

  摘要：

  已经描述了用于制备对称和不对称的古细菌四醚样类似物的合成途径。合成是基于从通用构件中精心修饰的半大环四醚脂质核心，然后同时或相继引入极性头基。设想了具有中性乳糖或磷脂酰胆碱极性头和阳离子甘氨酸甜菜碱部分的四醚脂质的功能化，既可以增加膜的稳定性，又可以表现出与带电核酸的相互作用。另外，还有效地合成了甘露糖和乳糖三天线簇，其被设计为用于与凝集素型受体选择性相互作用的多价配体。

  DOI：

  10.1021/jo071181r
• 作为试剂：
  描述：

  S-[(2R)-1-hexadecoxy-3-trityloxypropan-2-yl] ethanethioate 在 2-溴乙基二氯膦酸酯 、 sodium methylate 、 boron trifluoride methanol complex 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 氯仿 为溶剂， 反应 5.75h， 生成 ((R)-1-Chloromethyl-2-hexadecyloxy-ethylsulfanylmethyl)-benzene
  参考文献：
  名称：

  A Stereoselective and Highly Practical Synthesis of Cytosolic Phospholipase A₂ Substrate, 2-S-Arachidonoyl-1-O-hexadecyl-sn-2-thioglycero-3-O-phosphocholine

  摘要：

  The substrate 1 of cytosolic phospholipase A(2) (cPLA(2)) is an ether-type thiophospholipid with arachidonic acid at the C-2 position and is required for the chromogenic assay for reliable and convenient high throughput screening. The original method of synthesis of 1 has significant problems, resulting in extremely low overall yield and purity. We developed a novel and highly practical method of preparing sufficient quantities of pure 1 for assay. Our synthetic sequence is started with commercially available 1,2-O-isopropylidene-sn-grycerol (5) and is based on the following key steps: trityl migration reaction of 10 with boron trifluoride etherate to form 13, phosphocholine-forming reaction of 13 to yield 15, and efficient conversion of 15 into 1 by deprotection of a trityl group and condensation with arachidonic acid. Our method offers a practical means of large-scale production of 1 with excellent high chemical purity, because of the introduction of arachidonic acid at the last step of the synthetic sequence.

  DOI：

  10.1021/jo970882t

文献信息

• On the preparation of some phospholipid analogues
  作者：Judith E. Browne、Richard T. Freeman、Jeremy C. Russell、Peter G. Sammes

  DOI：10.1039/a910266n

  日期：——

  Several structural analogues of the biocompatible diacyl glycerol phosphatidylcholine family have been prepared. Considerable variation in structure is allowed without impairing the desirable biocompatible properties. In particular, derivatives in which the fatty ester link is replaced by ether links and in which the central glycerol group is replaced by simple variants such as the symmetrical tris(hydroxymethyl)ethane group retain biocompatible properties.

  已制备了生物相容性二酰基甘油磷脂酰胆碱家族的若干结构类似物。在不损害理想的生物相容性特性的前提下，结构允许相当大的变化。特别是，当脂肪酸酯键被醚键取代，以及中央甘油基团被对称的三羟甲基乙烷等简单变体取代时，这些衍生物仍能保持生物相容性特性。
• A Lipid-Lipase Aggregate with Ether Linkage as a New Type of Immobilized Enzyme for Enantioselective Hydrolysis in Organic Solvents.
  作者：Hiroyuki AKITA、Isao UMEZAWA、Hiroko MATSUKURA、Takeshi OISHI

  DOI：10.1248/cpb.40.318

  日期：——

  For the purpose of carrying out smoothly enzymatic reaction of water-insoluble substrates in organic solvents, a new type of immobilized enzyme, a lipid-lipase aggregate, was developed. In order to prepare various kinds of lipid-lipase aggregates, 27 kinds of dialkyl ether-type phospholipid analogues were newly synthesized and used for the preparation of aggregates with lipase. Thus obtained lipid-lipase aggregates were found to catalyze the enantioselective hydrolysis of the (±)-α-acyloxy ester 2 much more efficiently than lipase immobilized with synthetic prepolymer (ENTP-4000) in water-saturated isopropyl ether. Namely. the reaction time became much shorter (2 to 3d for completion as compared with 21 d) and the chemical and optical yields of the reaction products were found to be high.

  为了顺利进行水不溶性底物在有机溶剂中的酶促反应，开发了一种新型的固定化酶——脂质-脂肪酶聚集体。为了制备各种脂质-脂肪酶聚集体，新合成了27种二烷基醚型磷脂类似物，并用于制备与脂肪酶的聚集体。所得的脂质-脂肪酶聚集体被发现能够比在水分饱和的异丙醚中通过合成预聚物（ENTP-4000）固定的脂肪酶更有效地催化（±）-α-酰氧基酯2的对映选择性水解。即，反应时间大大缩短（完成需要2至3天，而之前需要21天），并且反应产物的化学和光学产率都很高。
• [EN] BIPOLAR TETRAETHER LIPIDS<br/>[FR] LIPIDES BIPOLAIRES DE TYPE TÉTRAÉTHER
  申请人：UNIV CALIFORNIA

  公开号：WO2017040702A1

  公开（公告）日：2017-03-09

  Disclosed herein, inter alia, are compounds, compositions, and liposomes and methods of thereof.

  披露的内容包括但不限于化合物、组合物、脂质体及其方法。
• Compounds for determining the activity of phospholipase A2
  申请人：Sirs-Lab GmbH

  公开号：US07301043B2

  公开（公告）日：2007-11-27

  Compounds for determining the activity of phospholipase A2, are described herein, and include embodiments having formula (1) wherein L1 is derived from an ether (R1—OR2)m, wherein R1 and R2 are independently selected and are derived from a hydrocarbon having 1 to 12 carbon atoms, with m being an integer from 1 to 4, or from a hydrocarbon R having 1 to 20 carbon atoms; F is unsubstituted or substituted pyrene as a flouraphore; Q is a quencher, and L2 is C(O)-L1 or C(O)-L1-NH, wherein L1 is as defined above. These compounds may be used to determine the activity of phospholipase A2, in particular PAF-AH.

  用于确定磷脂酶A2活性的化合物在此处描述，并包括具有以下式（1）的实施例 其中 L1源自醚（R1—OR2）m，其中R1和R2独立选择并源自具有1至12个碳原子的碳氢化合物，m为1至4的整数，或源自具有1至20个碳原子的碳氢化合物R; F是未取代或取代的芘作为荧光素; Q是一个猝灭剂，以及 L2是C(O)-L1或C(O)-L1-NH，其中L1如上定义。这些化合物可用于确定磷脂酶A2的活性，特别是PAF-AH。
• Hybrid Lipids Inspired by Extremophiles and Eukaryotes Afford Serum‐Stable Membranes with Low Leakage
  作者：Takaoki Koyanagi、Kevin J. Cao、Geoffray Leriche、David Onofrei、Gregory P. Holland、Michael Mayer、David Sept、Jerry Yang

  DOI：10.1002/chem.201701378

  日期：2017.5.17

  strategy (lipid tethering or cholesterol incorporation) to increase membrane integrity. Molecular dynamics simulations reveal that tethering of lipid tails and integration of cholesterol both reduce the disorder in lipid tails and time-dependent variance in area per lipid within a membrane, leading to tighter lipid packing. These hybrid lipid membranes have exceptional stability in serum, yet can support

  本文提出了一种新的杂种脂质，融合了古细菌使用的脂质尾巴分子束缚和真核生物使用的胆固醇基团整合的思想，从而利用了自然界采用的两种策略来增加膜中脂质的堆积。与仅使用一种策略（脂质束缚或胆固醇掺入）增加膜完整性的脂质体相比，由纯杂种脂质组成的脂质体在小离子和分子的膜泄漏中表现出5-30倍的减少。分子动力学模拟显示，脂质尾部的束缚和胆固醇的整合都可以减少脂质尾部的紊乱和膜内每个脂质的面积随时间的变化，从而导致脂质堆积更紧密。这些杂化脂质膜在血清中具有出色的稳定性，