苯乙醇-D5 | 35845-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯乙醇-D5
• 英文名称: phenylethanol-d5
• 英文别名: [phenyl-2H5]phenylethyl alcohol；ring-deuterated phenyl ethanol；2-phenylethanol-d₅；2-<²H5>Phenylaethanol；2-pentadeuteriophenyl-ethanol；Benzeneethanol-d5；2-(2,3,4,5,6-pentadeuteriophenyl)ethanol
• CAS: 35845-63-7
• 化学式: C₈H₁₀O
• 分子量: 127.127
• InChiKey: WRMNZCZEMHIOCP-RALIUCGRSA-N

物化性质

• 溶解度：
  可溶于氯仿（少量）、DMSO（少量）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

制备方法与用途

2-苯基乙醇-d5是氘标记的2-苯基乙醇[1]。2-苯基乙醇，又称苯乙醇或苯乙醇，是一种无色液体，从玫瑰、康乃馨、风信子、阿勒颇松、橙花等生物中提取。它具有宜人的花香，并且由真菌白色念珠菌产生的一种自身抗生素[2]。由于其在基本条件下的稳定性，2-苯基乙醇-d5被用作香烟中的添加剂和肥皂中的防腐剂。

反应信息

• 作为反应物：
  描述：

  苯乙醇-D5 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以36%的产率得到(2-溴乙基)苯-D5
  参考文献：
  名称：

  用于代谢研究的[苯基-2H5]葡糖苷酸及其代谢物的合成

  摘要：

  描述了从 [2H5] 溴苯开始合成氘标记的芥子油苷，[2H5]gluconasturtiin。还描述了硫代葡萄糖苷的潜在代谢物，即 [苯基-2H5] 苯乙基异硫氰酸酯、腈、硫氰酸酯、胺和苯乙基异硫氰酸酯的巯基酸共轭物。该系列化合物已制备用于喂养研究，以检查葡糖苷酸的哺乳动物代谢并寻找新的暴露生物标志物。版权所有 © 2005 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1004
• 作为产物：
  描述：

  氘代苯 在 溴 、 铁粉 、 magnesium 作用下， 以 乙醚 为溶剂， 生成 苯乙醇-D5
  参考文献：
  名称：

  A resonance Raman investigation on the interaction of styrene and 4-methyl styrene oligomers on sulphated titanium oxide

  摘要：

  In order to understand the nature of the interaction that gives rise to the yellow-orange colour observed when styrene or 4-methyl styrene are put in contact with sulphated TiO2, the resonance Raman spectra of such systems, including deuterated styrene (ring-deuterated d(5) and perdeuterated d(8)) and allylbenzene were investigated. In all cases a substantial enhancement of the ring v(CC) stretching mode was observed. A charge transfer process involving a transition from the ring pi-electrons to the empty d-pi orbitals of titanium was ascribed responsible for the absorption in the visible. Two types of resonance Raman spectra were observed depending on the excitation wavelength which can be explained by the presence of two kinds of oligomers, saturated and unsaturated, on the surface of the oxide with the former giving rise to a Raman enhancement at a higher excitation energy. (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1386-1425(99)00128-6

文献信息

• Distal Weak Coordination of Acetamides in Ruthenium(II)‐Catalyzed C−H Activation Processes
  作者：Qingqing Bu、Torben Rogge、Vladislav Kotek、Lutz Ackermann

  DOI：10.1002/anie.201711108

  日期：2018.1.15

  C−H activations with challenging arylacetamides were accomplished by versatile ruthenium(II) biscarboxylate catalysis. The distal C−H functionalization offers ample scope—including twofold oxidative C−H functionalizations and alkyne hydroarylations—through facile base‐assisted internal electrophilic‐type substitution (BIES) C−H ruthenation by weak O‐coordination.

  具有挑战性的芳基乙酰胺的CH活化是通过通用的双羧酸钌（II）催化完成的。远端C H功能化提供了广泛的范围-包括双重的氧化C H H功能化和炔烃加氢芳基化-通过弱O配位通过碱辅助的内部亲电子型取代（BIES）CH H钌化。
• Palladium‐Catalyzed Distal C−H Selenylation of 2‐Aryl Acetamides with Diselenides and Selenyl Chlorides
  作者：Meicui He、Linghui Gu、Yuqiang Tan、Yang Wang、Yuchi Wang、Chunran Zhang、Wenbo Ma

  DOI：10.1002/adsc.202000948

  日期：2020.12.22

  selenylation of the 2‐aryl acetamides assisted with removable 8‐aminoquinoline with readily available diselenides and selenyl chlorides has been developed. This selenylation reaction is scalable and tolerates a wide range of functional groups, providing a straightforward way of the preparing unsymmetrical diaryl selenides and dibenzoselene‐pinone. Preliminary mechanistic studies indicated that a single‐electron

  已经开发了一种方便有效的钯催化2-芳基乙酰胺的CH H硒化反应的方法，该方法辅以可移动的8-氨基喹啉，以及容易获得的二硒化物和硒基氯。硒化反应具有可扩展性，并能耐受各种官能团，为制备不对称的二芳基硒化物和二苯并硒酮提供了直接的方法。初步的机理研究表明，单电子转移型机理和CH-H金属易化是可行的。
• Preparation of deuterium labelled styrenes and divinylbenzenes
  作者：Nick Henry Werstiuk、George Timmins

  DOI：10.1139/v86-179

  日期：1986.6.1

  Specifically deuteriated styrenes (1-d, 2,2′-d₂, and ring labelled), perdeuteriostyrene, and specifically deuteriated divinylbenzenes (1,1′-d₂,2,2,2′,2′-d₄, and ring labelled) have been prepared by transforming suitably labelled phenylacetic (hydride or deuteride reduction and dehydration by solid KOH) and phenylenediacetic acids (esterification, hydride or deuteride reduction, and dehydration by solid KOH), respectively.

  具体氘代苯乙烯（1-氘，2,2′-二氘，和环标记）、全氘代苯乙烯和具体氘代二乙烯基苯（1,1′-二氘，2,2,2′,2′-四氘，和环标记）已通过适当标记的苯乙酸（通过固体KOH的氢化物或氘化物还原和脱水）和苯基乙二酸（酯化，氢化物或氘化物还原，和固体KOH的脱水）的转化而制备。
• Etude structurale de derives du phenyl-ethane
  作者：J.P. Lere-Porte、A. Bonniol、J. Petrissans、Cl. Charlon、G. Luu-Duc

  DOI：10.1016/0022-2860(83)90009-1

  日期：1983.3

  derivatives is consistent with the existence of trans-gauche conformational equilibria in the dissolved state. The relative amounts of each conformer have been determined and agree well with previous determinations. A theoretical study of the rotational isomerism has been carried out by the PCILO method for 1-phenyl-2-chloroethane and 1-phenyl-1-fluoro-2chloroethane. The relative stability and polarity of

  摘要 苯基乙烷衍生物的亚甲基弯曲模式的分析与溶解状态下反式构象平衡的存在是一致的。每个构象异构体的相对数量已经确定并且与之前的确定非常吻合。通过 PCILO 方法对 1-苯基-2-氯乙烷和 1-苯基-1-氟-2-氯乙烷进行了旋转异构的理论研究。trans 和 gauche 异构体的相对稳定性和极性与实验数据非常一致。
• On the generation and characterization of the spiro[2,5]octadienyl anion in the gas phase
  作者：Wilfrid P. M. Maas、Peter A. Van Veelen、Nico M. M. Nibbering

  DOI：10.1002/oms.1210240807

  日期：1989.8

  AbstractThree routes have been explored in both a high‐pressure chemical ionization (CI) source and a low‐pressure Fourier transform ion cyclotron resonance (FT‐ICR) cell to generate the spiro[2,5]octadienyl anion in the gas phase: (i) proton abstraction from spiro[2,5]octa‐4,6‐diene; (ii) expulsion of trimethysilyl fluoride by phenyl ring participation following fluoride anion attack upon the silicon centre of 2‐phenylethyl trimethylsilane; and (iii) collisionally induced dissociation (CID) of the carboxylate anion of 3‐phenylpropanoic acid via carbon dioxide loss. From comparison of the CID spectra of various reference [C8H9]− ions with those of the [C8H9]− ions which could be generated via the routes (i) and (iii) in the CI source it can be concluded that only the third route yields a [C8H9]−ion whose CID spectrum is not inconsistent with the one expected for the spiro[2,5]octadienyl anion. In the FT‐ICR cell [C8H9]− ions are generated along all three routes; their structures have been identified by specific ion‐molecule reactions and appear to be different. Route (i) yields an α‐methyl benzyl anion, probably due to isomerization within the ion‐molecule complex formed. An ortho‐ethylphenyl anion is formed along route (ii), presumably due to an intramolecular ortho proton abstraction in the generated trimethylsilyl fluoride solvated 2‐phenylethyl primary carbanion. The [C8H9]− ion formed along route (iii) shows reactions similar to those of the 1,1‐dimethylcyclohexadienyl anion which is structurally related to the spiro[2,5]octadienyl anion. Furthermore, the [C8H9]− ion generated via route (iii) reacts with hexafluorobenzene under expulsion of only one hydrogen fluoride molecule which contains exclusively one of the original phenyl ring hydrogen atoms. On the basis of all these observations it is therefore quite likely that the spiro[2,5]octadienyl anion is formed by collisionally induced decarboxylation of the 3‐phenylpropanoic acid carboxylate anion and can be a long‐lived and stable species in the gas phase.