1,32-dotriacontanediol | 85756-62-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,32-dotriacontanediol
• 英文别名: dotriacontane-1,32-diol
• CAS: 85756-62-3
• 化学式: C₃₂H₆₆O₂
• 分子量: 482.875
• InChiKey: NMHYYHYTDQOLCA-UHFFFAOYSA-N

物化性质

• 熔点：
  115-116 °C
• 沸点：
  578.9±23.0 °C(Predicted)
• 密度：
  0.875±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  34
• 可旋转键数：
  31
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,32-dotriacontanediol 在 水 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 乙腈 为溶剂， 反应 74.0h， 生成 32-{[hydroxy(2-hydroxyethoxy)phosphoryl]oxy}dotriacontan-1-yl-{2-[N-3-(dimethylaminopropyl)-N,N-dimethylammonio]ethylphosphate}
  参考文献：
  名称：

  Synthesis of Novel Asymmetrical Single-Chain Phosphoglycol-Based Bolaamphiphiles

  摘要：

  The synthesis of long-chain 1,-diols with orthogonal cleavable protecting groups can be effectively performed with the use of the Grignard coupling reaction, successfully leading to the preparation of novel asymmetrical single-chain phosphoglycol-based bolaamphiphilesa side-product that always occurred during the synthesis of symmetrical bolalipids. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.825806
• 作为产物：
  描述：

  16-溴-1-十六烷醇 在 4-甲基苯磺酸吡啶 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 1,32-dotriacontanediol
  参考文献：
  名称：

  一系列单链1，omega-bis（phosphocholines）的一般合成和聚集行为。

  摘要：

  描述了一系列具有22至32个碳原子的偶数链长的聚亚甲基-1，ω-双（磷酸胆碱）的合成和理化特性。提出了两种新的合成策略，用于制备长链1，ω-二醇作为烃类结构单元。通过低温透射电子显微镜（cryo-TEM），差示扫描量热法（DSC）和傅里叶变换红外光谱（FTIR）研究了单链双亲性嗜蓝菌的温度依赖性自组装。

  DOI：

  10.1002/chem.200601866

文献信息

• Structure–property relationships in a series of diglycerol tetraether model lipids and their lyotropic assemblies: the effect of branching topology and chirality
  作者：Thomas Markowski、Simon Drescher、Annette Meister、Alfred Blume、Bodo Dobner

  DOI：10.1039/c4ob00048j

  日期：——

  preparation of diglycerol tetraethers was either performed by condensing suitable blocked monoglycerol diethers by Grubbs metathesis or by reaction of the transmembrane C32-chain with blocked glycerols followed by further alkylation steps. Finally, we could show that the resulting lipids can form closed lipid vesicles comparable to the optically pure counterparts. Therefore, these much simpler lipids compared

  合成了三种具有一条跨膜链的新型二甘油四醚脂质。这些脂质在疏水链的选定位置仅包含两个或四个外消旋甲基分支，这与来自具有类异戊二烯取代模式的古细菌膜的天然脂质相反。甲基部分的插入是从任一（RS）-香茅基溴化物或廉价的甲基丙二酸乙酯。对于链延长，使用Cu催化的格氏试剂偶联反应。甘油二醚的制备通过通过Grubbs复分解缩合合适的封闭单甘油二醚或通过跨膜C32链与封闭甘油的反应进行，然后进行进一步的烷基化步骤来进行。最后，我们可以证明所得的脂质可以形成与光学纯的脂质相当的闭合脂质囊泡。因此，与来自古细菌膜的天然脂质相比，这些简单得多的脂质也适用于制备稳定的定制脂质体。
• Chain Multiplication of Fatty Acids to Precise Telechelic Polyethylene
  作者：Timo Witt、Manuel Häußler、Stefanie Kulpa、Stefan Mecking

  DOI：10.1002/anie.201702796

  日期：2017.6.19

  double bond of the α,ω‐dicarboxylic fatty acid self‐metathesis products is shifted selectively to the statistically much‐disfavored α,β‐position in a catalytic dynamic isomerizing crystallization approach. “Chain doubling” by a subsequent catalytic olefin metathesis step, which overcomes the low reactivity of this substrates by using waste internal olefins as recyclable co‐reagents, yields ultra‐long‐chain

  从常见的单不饱和脂肪酸开始，揭示了一种策略，该策略通过两个可扩展的催化步骤序列提供超长的脂肪族α，ω-双官能结构单元，实际上使起始原料的链长增加了一倍。在催化动态异构化结晶方法中，α，ω-二羧酸脂肪酸自复分解产物的中心双键选择性地转移到统计学上不利的α，β-位置。通过随后的催化烯烃复分解步骤实现“链加倍”，该步骤通过使用废弃的内部烯烃作为可回收的共试剂克服了这种底物的低反应性，从而产生了具有精确链长的超长链α，ω-双官能结构单元，如C 48所示链。这些结构的独特性体现在由这些遥螯单体产生的脂肪族聚酯的无与伦比的熔点（T m = 120°C），以及它们自组装成聚乙烯类单晶的过程。
• General Synthesis and Aggregation Behaviour of New Single-Chain Bolaphospholipids: Variations in Chain and Headgroup Structures
  作者：Simon Drescher、Annette Meister、Gesche Graf、Gerd Hause、Alfred Blume、Bodo Dobner

  DOI：10.1002/chem.200800033

  日期：2008.7.28

  The chemical structures of polymethylene-1,omega-bis(phosphocholines) that self-assemble into nanofibres was modified on the one hand in the hydrophobic chain region, by introduction of sulfur and oxygen atoms, and on the other hand by variation of the polar headgroup structure with functionalised tertiary amines. The temperature-dependent self-assembly of these novel bolaphospholipids into nanofibres

  自组装成纳米纤维的聚亚甲基-1，ω-双（磷酸胆碱）的化学结构一方面在疏水链区域中通过引入硫和氧原子而被修饰，另一方面通过极性的变化而被修饰。带有官能化叔胺的头基结构。通过差示扫描量热法（DSC）和透射电子显微镜（TEM）研究了这些新型的硼磷脂到纳米纤维和球形胶束中的温度依赖性自组装。纳米纤维的热稳定性强烈取决于头基和疏水链的化学组成。通过点击化学在头基区域中插入新功能，使得这些物质对于生物科学和材料科学中的潜在应用很有趣。
• Chain Length Dependence of Intramolecular Excimer Formation with 1,<i>n</i>-Bis(1-pyrenylcarboxy)alkanes for <i>n</i> = 1−16, 22, and 32
  作者：Klaas A. Zachariasse、Antonio L. Maçanita、Wolfgang Kühnle

  DOI：10.1021/jp991611k

  日期：1999.10.1

  Time-resolved and photostationary measurements in alkane solvents as a function of temperature are presented for the 1,n-bis(1-pyrenylcarboxy)alkanes (1PC(n)1PC, n = 1-16, 22, 32) with n methylene groups in the chain. For all compounds except 1PC(1)1PC intramolecular excimer fluorescence is observed. From fluorescence decay analysis and quenching data, the rate constant k(a) of excimer formation in the series 1PC(n)1PC is determined as a function of chain length. The value of k(a), as well as that of the excimer-to-monomer fluorescence quantum yield ratio Phi'/Phi, peaks at n = 5 and then gradually decreases with increasing n. These results are in clear contrast to those obtained previously with the 1,n-di(1-pyrenyl)alkanes (1Py(n)1Py), where Phi'/Phi, reaches its maximum at n = 3, with a sharp minimum (no excimer formation) at n = 7. This difference is attributed to a reduced steric hindrance at the excimer configuration (k(a)) and to dimer formation in the electronic ground state between the pyrenylcarboxy end groups in 1PC(n)1PC (Phi'/Phi). Both effects arise from the absence of methylene hydrogens next to the pyrenyl moieties of these molecules, which hydrogens prevent excimer formation in the case of 1Py(7)1Py.
• Synthesis of new bifluorophoric probes adapted to studies of donor-donor electronic energy transfer in lipid systems
  作者：Irina V Grechishnikova、Lennart B.-Å Johansson、Julian G Molotkovsky

  DOI：10.1016/0009-3084(96)02537-6

  日期：1996.6

  A series of bifluorophoric fluorescent probes with identical pairs of chromophores have been synthesized. The fluorophores are 9-anthryl, 3-perylenyl and rhodamine 101, and they are separated by a long rigid (bisteroid) or flexible (dotriacontane) diol spacer. The probes are designed for studies of intra- and intermolecular electronic energy transfer in lipid systems such as model and biological membranes. They are shown to incorporate in phosphatidylcholine vesicles with an hitherto unknown orientation.