1-(2,2-2H2)-butanol | 70639-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,2-2H2)-butanol
• 英文别名: [2,2-d2]-1-butanol；[2,2-2H]2-butanol；n-butanol-2,2-d2；butanol-3,3-d2；2,2-dideuterio-butan-1-ol；<2,2-D2>-1-Butanol；2,2-Dideuteriobutan-1-ol
• CAS: 70639-32-6
• 化学式: C₄H₁₀O
• 分子量: 76.1069
• InChiKey: LRHPLDYGYMQRHN-SMZGMGDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  5
• 可旋转键数：
  2
• 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

反应信息

• 作为反应物：
  描述：

  1-(2,2-2H2)-butanol 在 硫酸 、 氢溴酸 作用下， 生成 溴丁烷-D2
  参考文献：
  名称：

  The formation of [CH3CH2C(OH)CH2]+˙ from 1-hepten-3-ol

  摘要：

  AbstractThe [C4H8O]+˙ ion in the mass spectrum of 1‐hepten‐3‐ol is shown to be \documentclass{article}\pagestyle{empty}\begin{document}$ {\rm{CH}}_{\rm{3}} {\rm{CH}}_{\rm{2}} {\rm{C(= }}\mathop {\rm{O}}\limits^{\rm{ + }} {\rm{H}})\mathop {\rm{C}}\limits^{\rm{.}} {\rm{H}}_{\rm{2}} $\end{document} by collisional activation spectra, appearance energies and comparison of the ratios of the intensities of metastable decompositions. [C4H8O]+˙ appears to be formed by rearrangement of ionized 1‐hepten‐3‐ol to \documentclass{article}\pagestyle{empty}\begin{document}$ {\rm{CH}}_{\rm{3}} \mathop {\rm{C}}\limits^{\rm{.}} {\rm{HC(= }}\mathop {\rm{O}}\limits^{\rm{ + }} {\rm{H)CH}}_{\rm{2}} {\rm{CH}}_{\rm{2}} {\rm{CH}}_{\rm{2}} {\rm{CH}}_{\rm{3}} $\end{document} followed by γ‐hydrogen rearrangement‐β‐cleavage.

  DOI：

  10.1002/oms.1210160704
• 作为产物：
  描述：

  丁醛-D2 在 lithium aluminium tetrahydride 、 三缩四乙二醇 作用下， 以 三甘醇二甲醚 为溶剂， 生成 1-(2,2-2H2)-butanol
  参考文献：
  名称：

  Raman spectroscopy of n-pentyl methyl ether and deuterium labelled analogues

  摘要：

  报告并讨论了正戊基甲醚（C5H11OCH3）及六种选择性氘标记的类似物的拉曼光谱。建立并完善了观察到的ν(sp3CH)拉伸和弯曲频带与烷基链中氘原子位置之间的相关性。将特定骨架振动与拉曼光谱中的频带关联也取得了类似的进展。强调了本研究在改善生物相关较大系统的拉曼光谱频带分配方面的重要性。版权 © 2010 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jrs.2595

文献信息

• Synthesis of sequentially deuterated 1-n-Butyl-3-methylimidazolium ionic liquids
  作者：Alexander Khrizman、Hiu Yan Cheng、Guillermo Moyna

  DOI：10.1002/jlcr.1884

  日期：2011.6.30

  Deuterium isotopologues of the ionic liquid (IL) 1–n-butyl-3-methylimidazolium chloride ([C4mim]Cl) sequentially labeled on the C-1″, C-1′, C-2′, C-3′, and C-4′ positions of the N-alkyl groups were prepared following a strategy that minimizes the number of distinct reactions through the use of analogous synthetic routes. In several cases, good yields after the initial deuterium incorporation reaction were achieved by combining well-established chemical transformations into efficient single-step processes. Copyright © 2011 John Wiley & Sons, Ltd.

  氘同位素的离子液体（IL）1–n-丁基-3-甲基咪唑氯化物（[C4mim]Cl）在N-烷基侧基的C-1″、C-1′、C-2′、C-3′和C-4′位点上逐步标记，采用了一种通过类似合成路径最小化不同反应数量的策略。在多个案例中，通过将成熟的化学转化结合为高效的单一步骤过程，初步氘掺入反应后获得了良好的产率。版权 © 2011 John Wiley & Sons, Ltd.
• Site-selective deuterium labeling of the tetrabutylammonium cation
  作者：Melissa J. Heinsen、Thomas C. Pochapsky

  DOI：10.1002/(sici)1099-1344(200004)43:5<473::aid-jlcr333>3.0.co;2-s

  日期：2000.4

  Four separate selectively deuterated samples of tetrabutylammonium iodide have been prepared in which each one of the four nonequivalent alkyl carbons is separately and fully deuterated. These samples were prepared for nuclear magnetic resonance (NMR) studies of the aggregation of ion pairs in low polarity solvents.
• Intermediacy of ion neutral complexes in the fragmentation of short-chain dialkyl sulfides
  作者：G. Filsak、H. Budzikiewicz

  DOI：10.1002/(sici)1096-9888(199906)34:6<601::aid-jms811>3.0.co;2-8

  日期：1999.6

  The main fragmentation processes after electron ionization of butyl methyl and butyl ethyl sulfides are rationalized by the intermediacy of the ion neutral complex [RSH . methylcyclopropane](+.) as demonstrated by extensive labeling and collision activation studies. Copyright (C) 1999 John Wiley & Sons, Ltd.
• Reactions of ionized dibutyl ether
  作者：Richard D. Bowen、Dennis Suh、Johan K. Terlouw

  DOI：10.1002/oms.1210291211

  日期：1994.12

  AbstractThe reactions of ionized di‐n‐butyl ether are reported and compared with those of ionized n‐butyl sec‐butyl and di‐sec‐butyl ether. The main fragmentation of metastable (CH3CH2CH2CH2)2O+. is C2H5⋅ loss (˜85%), but minor amounts (2–4%) of CH3⋅, C4H7⋅, C4H9⋅, C4H10 and C4H10O are also eliminated. In contrast, C2H5⋅ elimination is of much lower abundance (20 and 4%, respectively) from metastable CH3CH2CH2CH2OCH(CH3)CH2CH3+. and [CH3CH2(CH3)CH]2O+., which expel mainly C2H6 and CH3⋅ (35–55%). Studies on collisional activation spectra of the C6H13O+ oxonium ions reveal that C2H5⋅ loss from (CH3CH2CH2CH2)2O+. gives the same product, (CH3CH2CH2CH2 +OCHCH3) as that formed by direct cleavage of CH3CH2CH2CH2OCH(CH3)CH2CH3+.. Elimination of C2H5⋅ from (CH3CH2CH2CH2)2O+. is interpreted by means of a mechanism in which a 1,4‐H shift to the oxygen atom initiates a unidirectional skeletal rearrangement to CH3CH2CH2CH2OCH(CH3)CH2CH3+., which then undergoes cleavage to CH3CH2CH2CH2+OCHCH3 and C2H5⋅. Further support for this mechanism is obtained from considering the collisional activation and neutralization‐reionization mass spectra of the (C4H9)2O+. species and the behaviour of labelled analogues of (CH3CH2CH2CH2)2O+.. The rate of ethyl radical loss is suppressed relative to those of alternative dissociations by deuteriation at the γ‐position of either or both butyl substituents. Moreover, C2H5⋅ loss via skeletal rearrangement and fragmentation of the unlabelled butyl group in CH3CH2CH2CH2OCH2CH2CD2CH3+. occurs approximately five times more rapidly than C2H4D⋅ expulsion via isomerization and fission of the labelled butyl substituent. These findings indicate that the initial 1,4‐hydrogen shift is influenced by a significant isotope effect, as would be expected if this step is rate limiting in ethyl radical loss.
• Unimolecular reactions of isolated organic ions: The chemistry of the oxonium ions CH3CH2CH2CH2+O = CH2 and CH3CH2CH2CH = O+CH3
  作者：Richard D. Bowen、Peter J. Derrick

  DOI：10.1002/oms.1210281035

  日期：1993.10

  AbstractThe reactions of the metastable oxonium ions CH3CH2CH2CH2+O = CH2 and CH3CH2CH2 = O+ CH3 are reported and discussed. Both these isomers of C5H11O+ expel predominantly CH2O (75–90% of the metastable ion current), a moderate amount of C3H6 (5–15%), a minor amount of CH3OH (2–8%) and a very small proportion of H2O (0.5–3%). All these processes give rise to Gaussian metastable peaks. The kinetic energy releases associated with fragmentation of these oxonium ions are similar, but slightly larger for dissociation of CH3CH2CH2CH = O+CH3. The behaviour of labelled analogues confirm that the reactions of CH3CH2CH2CH = O+CH3 are closely related, but subtly different. Elimination of CH2O and C3H6 is intelligible by means of mechanisms involving CH3CH+CH2CH2OCH3. This open‐chain cation is accessible to CH3CH2CH2 +O = CH2 by a 1,5‐H shift and to CH3CH2CH2‐CH = O+CH3 by two consecutive 1,2‐H shifts (or, possibly, a direct 1,3‐H shift). The rates of these 1,2‐, 1,3‐ and 1,5‐H shifts are compared with one another and also with the rates of CH2O and C3H6 loss from each of the two oxonium ions. The 1,5‐H shift that converts CH3CH+CH2CH2OCH3 formed from CH3CH2CH2CH = O+ CH3 into CH3CH2CH2+O = CH2 prior to CH2O elimination is essentially unidirectional. In contrast, the corresponding step converting C5H11O+ ions generated as CH3CH2CH2CH2+O = CH2 into CH3CH+ CH2CH2OCH3 competes effectively with expulsion of CH2O and C3H6. The implications of the latter finding for the degree of concert in the hydrogen transfer and carbon‐carbon bond fission steps in alkene losses from oxonium ions via routes that are formally isoelectronic with the retro ‘ene’ pericyclic process are emphasized.