硬脂醇-D2 | 86369-69-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 硬脂醇-D2
• 英文名称: <1,1-d2>stearyl alcohol
• 英文别名: n-octadecyl-1,1-D2 alcohol；1,1-d2-octadecanethiol；[1,1-2H2]-octadecanol；1-octadecanol-1,1-d2；1,1-d2-octadecanol；[1,1-d2]stearyl alcohol；1,1-dideuteriooctadecan-1-ol
• CAS: 86369-69-9
• 化学式: C₁₈H₃₈O
• 分子量: 272.483
• InChiKey: GLDOVTGHNKAZLK-CPLZMPMBSA-N

物化性质

• 熔点：
  57.0-59.0 °C(Solv: acetonitrile (75-05-8))

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  19
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

制备方法与用途

1-羟基十八烷-d₂是氘标记的1-羟基十八烷基[1]。这种化合物是一种内源性的代谢产物。

反应信息

• 作为反应物：
  描述：

  硬脂醇-D2 在 diphenylphosphinopolystyrene 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 2,2-d2-nonadecanonitrile
  参考文献：
  名称：

  同位素标记脂肪酸的快速合成方法：2,2-d2-壬酸的制备

  摘要：

  我们描述了一种新的合成途径，用于通过将羧酸直接转化为 2,2-二氘代同源物的同源程序来制备同位素标记的饱和奇数脂肪酸。该过程可用于从羧酸开始获得奇数和偶数的 2,2-双氘化脂肪酸。此外，该过程的重复也可用于合成多氘化脂肪酸，其中重原子位于相邻的碳原子上或在分子中以不同的方式排列。版权所有 © 2006 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1094
• 作为产物：
  描述：

  硬脂醇 在 5% activated charcoal-supported ruthenium catalyst 、 氢气 、 重水 作用下， 80.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以95%的产率得到硬脂醇-D2
  参考文献：
  名称：

  一种方便有效的区域选择性氘化方法

  摘要：

  通过在碳上使用5％钌（Ru / C），氢气和氧化氘（D 2 O）的组合，可以实现邻位碳上羟基的便捷和区域选择性氘化。

  DOI：

  10.1002/adsc.200800407

文献信息

• Oxygen-Independent Decarbonylation of Aldehydes by Cyanobacterial Aldehyde Decarbonylase: A New Reaction of Diiron Enzymes
  作者：Debasis Das、Bekir E. Eser、Jaehong Han、Aaron Sciore、E. Neil G. Marsh

  DOI：10.1002/anie.201101552

  日期：2011.7.25

  Just add water: Structurally, cyanobacterial aldehyde decarbonylases are members of the non‐heme diiron oxygenase family of enzymes. However, the enzyme catalyzes the hydrolysis of aliphatic aldehydes to alkanes and formate (see scheme), in an oxygen‐independent reaction. This unusual and chemically difficult reaction most likely involves free radical intermediates.

  只需加水：在结构上，蓝藻醛脱羰酶是非血红素二铁加氧酶家族的成员。然而，该酶在不依赖于氧的反应中催化脂肪醛水解为烷烃和甲酸酯（见方案）。这种不寻常且化学上困难的反应很可能涉及自由基中间体。
• Synthesis of deuterated 5-n-alkylresorcinols
  作者：Kirsti Parikka、Kristiina Wähälä

  DOI：10.1002/jlcr.1463

  日期：2008.1

  Four alternative strategies for the preparation of deuterium poly-labelled 5-n-alkylresorcinols are explored. Ring-labelled 2H3-alkylresorcinols synthesized by acidic H/D exchange are stable under electrospray ionization MS conditions but scrambling occurs in electron bombardment ionization MS. Side chain-labelled 2H4-derivatives prepared by two different total synthesis approaches are contaminated by isotopologues with varying number of deuterium labels due to H/D redistribution and exchange during D2 gas deuterogenation. The derivative carrying an ω-2H3 label is isotopically pure and completely stable under all relevant analytical conditions encountered in quantitation work. Copyright © 2008 John Wiley & Sons, Ltd.

  本研究探讨了制备氘多标记 5-正烷基间苯二酚的四种替代方法。通过酸性 H/D 交换合成的环状标记 2H3- 烷基间苯二酚在电喷雾电离质谱条件下是稳定的，但在电子轰击电离质谱条件下会出现扰乱。通过两种不同的全合成方法制备的侧链标记 2H4-衍生物在 D2 气体氘代化过程中由于 H/D 的重新分布和交换而受到氘标记数量不同的同位素的污染。带有 ω-2H3 标记的衍生物在定量工作中遇到的所有相关分析条件下都是同位素纯的，而且完全稳定。Copyright © 2008 John Wiley & Sons, Ltd. All Rights Reserved.
• A study of the structure and dynamics of dimethyloctadecylsilyl-modified silica using wide-line 2H NMR techniques
  作者：Robert C. Zeigler、Gary E. Maciel

  DOI：10.1021/ja00017a001

  日期：1991.8

  The structure and dynamics of dimethyloctadecylsilyl-modified silica gel (C18-silica) were studied by using solid-state H-2 NMR techniques. In order to reproduce with a theoretical model the H-2 line shapes that were observed for the C18-silica samples, it was necessary to assume that a variety of environments are present on the C18-silica surface and that this heterogeneity results in different details of the motion of silane groups that are bonded to different regions of the C18-silica surface. H-2 spectra that were taken on the C18-silica samples at temperatures below room temperature appear to be superpositions of two line shapes, indicating that some silane groups move with a simple two-site jump motion, along with others that move with a more complex distribution of motions. At -50-degrees-C, the addition of wetting liquids can affect the H-2 line shape; different liquids can have dramatically different effects on the observed H-2 line shapes. Simple surface structures for Cl8-silica are proposed that are consistent with the NMR data observed in this study.
• Structure and Dynamics in Alkanethiolate Monolayers Self-Assembled on Gold Nanoparticles:  A DSC, FT-IR, and Deuterium NMR Study
  作者：Antonella Badia、Louis Cuccia、Linette Demers、Fred Morin、R. Bruce Lennox

  DOI：10.1021/ja963571t

  日期：1997.3.1

  Gold nanoparticles, cn. 30 Angstrom in diameter, have been derivatized with specifically deuterated (position 1 and positions 10 to 13) and perdeuterated (positions 2 to 18) octadecanethiols (C18SH). The phase behavior of the octadecanethiolate monolayers chemisorbed onto the colloidal Sold surface was characterized by differential scanning calorimetry(DSC). The DSC thermograms show that the C18SH-derivatized Au nanoparticles undergo distinct phase transitions which can be associated with the reversible disordering of the alkyl chains. Despite the highly curved geometry of these Au particles, there is a remarkable degree of conformational order in the alkanethiolate chains and the thermotropic behavior of the thiol-modified gold nanoparticles is very similar to that of conventional, planar self-assembled monolayers. Both the peak maximum temperature and the enthalpy associated with the DSC transition strongly parallel those of the gel-to-liquid crystalline transition of n-diacylphosphatidylcholine lipid bilayer membranes of equivalent chain length. Restricted chain mobility due to covalent bonding of the sulfur head group to the gold surface does not affect the cooperativity of the transition in terms of the transition temperature and enthalpy. Local chain ordering and dynamics in the deuterated C18S/Au nanoparticles have been probed using variable-temperature solid-state deuterium NMR spectroscopy and transmission FT-IR spectroscopy. The temperature dependence of the symmetric CD2 stretching frequency has confirmed that the DSC-detected phase transition involves a thermally-induced change from a predominantly all-trans conformation to a chain disordered state. A comparison of the thermal behavior of d(35)-C18S/Au and 10,10, II, II, IZ, 12, 13, 13-d(8)-C18S/Au shows that disordering originates in the chain terminus region and propagates toward the middle of the chain as the temperature increases, Studies of I,1-d(2)-C18S/Au show that the disorder does not extend to the tethered sulfur head group. Deuterium NMR spectroscopy specifically establishes that chain melting arises from an increased frequency of gauche bonds in the alkanethiolate chains. The H-2 NMR line shapes further indicate that the tethered alkanethiolate chains are undergoing rapid trans-gauche bond isomerization and axial chain rotation.
• The nominal butyl ester ion in the mass spectra of long-chainn-alkyl esters: A postscript
  作者：Seymour Meyerson、Eugene S. Kuhn、Imre Puskas、Ellis K. Fields、Leonard C. Leitch、Thomas A. Sullivan

  DOI：10.1002/oms.1210180305

  日期：1983.3

  Abstractn‐Octadecyl benzoate, taken as a model for long‐chain n‐alkyl carboxylates generally, loses C14H28 under electron impact to yield a product with the same elemental composition as the butyl benzoate molecular ion. This product retains quantitatively one hydrogen from C‐6, and seems to be formed as an oxygen‐protonated 4‐benzoyloxybutyl radical. It reacts further to lose H2O, in which deuterium labeling demostrates that the second hydrogen atom comes predominantly from C‐4. The intermediate reorganization, for which the driving force is presumably furnished by the instability associated with a primary radical, is pictured in terms of cyclization via bonding between the C‐4 radical site and the benzoyl carbon concerted with hydrogen migration via a 4‐membered quasicyclic transition state.