<2-2H1>acrolein | 10317-37-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <2-2H1>acrolein
• 英文别名: <2-2H>acrolein；2-[D₁]acrolein；acrolein-2-d；acrolein-d1；[2-2H]acrolein
• CAS: 10317-37-0
• 化学式: C₃H₄O
• 分子量: 57.0562
• InChiKey: HGINCPLSRVDWNT-VMNATFBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  4.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  <2-2H1>acrolein 、 phenylmagnesium bromide 以58%的产率得到1-phenyl<2-2H1>prop-2-en-1-ol
  参考文献：
  名称：

  气相碳负离子重排。去质子化的苄基和烯丙基醚

  摘要：

  以下系统进行了研究：（i）所述离子的PhO博士2上碰撞活化经历重排的Wittig至pH 3 CO -碎裂之前; （ii）PhO HCH CH 2经历竞争性重排，即。Wittig重排为Ph（CH 2 CH）CHO –阴离子Claisen重排为（HO）去质子化的邻烯丙基苯酚，前者占优势。（iii）二苄基醚的去质子化反应产生不稳定的物质，形成PhCH 2 –：尽管在缩合相中发生，但在气相中未观察到Wittig重排；和（iv）PhCH 2OCH 2 CH CH 2去质子化以形成两个可相互转换的阴离子Ph HOCH 2 CH CH 2和PhCH 2 O HCH CH 2，前者更稳定。两种离子均产生少量的维蒂希产物，但主要过程是损失H 2 O形成去质子化的二氢萘。在该系统中，气相反应和冷凝相反应之间存在一些类比。烯丙基苄基醚在强制条件下的缩合反应（二异丙基氨基锂/四氢呋喃-六甲基磷酰胺）得到产物1-苯基-丁-3-烯-1-醇，1

  DOI：

  10.1039/p29880000497
• 作为产物：
  描述：

  生成 <2-2H1>acrolein
  参考文献：
  名称：

  Nucleophilic attack at αβ-unsaturated carbonyl systems. The reactions of acrolein and methyl acrylate with CF₃O^–, [F^–⋯ HOMe], RO^–, and [RO^–⋯ HOR]. An ab initio and ion cyclotron resonance study

  摘要：

  DOI：

  10.1039/p29830001337

文献信息

• Vanadium-Catalyzed Deoxydehydration of Glycerol Without an External Reductant
  作者：Allan R. Petersen、Lasse B. Nielsen、Johannes R. Dethlefsen、Peter Fristrup

  DOI：10.1002/cctc.201701049

  日期：2018.2.21

  vanadium‐catalysed deoxydehydration (DODH) of neat glycerol has been developed. Cheap and readily available ammonium metavanadate (NH4VO3) affords higher yields of allyl alcohol than the well‐established catalyst methyltrioxorhenium. A study in which deuterium‐labelled glycerol was used was undertaken to further elucidate the dual role of glycerol as both an oxidant and reductant. This study led to

  已开发出纯甘油的钒催化脱氧脱水（DODH）。廉价且容易获得的偏钒酸铵（NH 4 VO 3）比公认的催化剂甲基三氧or可提供更高的烯丙醇收率。进行了一项使用氘标记甘油的研究，以进一步阐明甘油作为氧化剂和还原剂的双重作用。这项研究导致提出了一种金属催化的DODH机理来生产烯丙醇，并加深了对副产物丙烯醛和丙醛的形成的认识。
• Decomposition of prop-2-ynylic N-oxides to acrolein and schiff bases via O-allenyl hydroxylamines
  作者：G. Hallström、B. Lindeke、A.H. Khuthier、M.A. Al-Iraqi

  DOI：10.1016/s0040-4039(01)85588-x

  日期：1980.1

  Prop-2-ynylic N-oxides rearrange thermally via O-allenyl hydroxylamines to acrolein and an imine. The second rearrangement step, falling in the class of thermal cis-eliminations, is shown with variously 2H-substituted pargyline N-oxides.

  丙-2-基N-氧化物通过O-烯基羟胺热重排为丙烯醛和亚胺。示出了属于热顺式消除类的第二重排步骤，其具有不同的2个H-取代的精氨酸N-氧化物。
• Molecular structure of s-cis- and s-trans-acrolein determined by microwave spectroscopy
  作者：C. E. Blom、G. Grassi、A. Bauder

  DOI：10.1021/ja00336a022

  日期：1984.11
• Infrared Reflection Absorption Spectroscopic Study on the Adsorption Structures of Acrolein on an Evaporated Silver Film
  作者：Shuji Fujii、Naoki Osaka、Masato Akita、Koichi Itoh

  DOI：10.1021/j100018a036

  日期：1995.5

  Infrared reflection absorption (IRA) spectra were measured for acrolein adsorbed on an evaporated silver film at 90 K under ultrahigh vacuum conditions. IRA spectra indicated that acrolein adsorbed on the silver substrate exists In a trans form and that, on increasing exposure levels, the adsorbate takes on type-A, -B, -C, and -D structures successively. The adsorption structures are characterized by the C=O stretching (nu(C=O)) and CH2 out-of-plane bending (omega(CH2)) bands; they are observed at 1670 and 978 cm(-1) (type-A). 1693 and 985 cm(-1) (type-B), 1699 and 995 cm(-1) (type-C), and 1691 and 993 cm(-1) (type-D). Type-A and -B interact directly with the substrate, while the type-C and -D form molecular layers on top of the type-A and -B layer. The intensity ratios, omega(CH2)/nu(C=O), observed for type-A, -B -C, and -D are appreciably larger than the ratio observed for acrolein in a polycrystalline state, indicating that all the adsorbates have the molecular plane more or less parallel to the substrate surface. In the CH out-of-plane bending vibration region, type-C and -D give the CH out-of-plane bending bands of the vinyl group and formyl group near 1018 and 1005 cm(-1), respectively, in addition to the omega(CH2) band, while type-A and -B give only the prominent band due to omega(CH2). This trend was observed also for acrylic acid lying flat on a silver substrate (Fujii, S.; et al. Surf. Sci. 1994, 306, 381). Thus, the selective enhancement of the omega(CH2) band seems to be a general feature for a planar molecule containing a vinyl group and interacting directly with the silver surface. Ab initio molecular orbital method at the RHF/4-31G* level was applied to calculate the normal vibrational frequencies of a free acrolein as well as a silver ion-acrolein complex; the results reproduced frequency differences between IRA bands of type-A and the corresponding bands of acrolein in a gas state. proving that type-A forms a coordination bond between the oxygen atom of the C=O group and a positively charged site of the substrate.