1-(trideuteriomethoxy)prop-2-ene | 78638-92-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(trideuteriomethoxy)prop-2-ene
• 英文别名: allyl methyl-d₃ ether；allyl methyl-d3 ether
• CAS: 78638-92-3
• 化学式: C₄H₈O
• 分子量: 75.0831
• InChiKey: FASUFOTUSHAIHG-BMSJAHLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  5.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(trideuteriomethoxy)prop-2-ene 以 氘代甲醇 为溶剂， 反应 148.0h， 生成 C₄H₅⁽²⁾H₃O
  参考文献：
  名称：

  （P（C（6）H（5））（3））CpRu（+）催化的烯丙基羧酸酯的脱保护。

  摘要：

  报道了使用过渡金属络合物对烯丙基羧酸酯进行脱保护的新的有效催化方法。反应以高的底物/催化剂比率进行，并且不使用额外的亲核试剂，以定量收率得到了脱保护的羧酸。也可以使用多种底物，包括多功能氨基酸和肽。与传统的钯催化方法相比，该新方法更加有效，安全且操作简单。

  DOI：

  10.1021/jo020281o
• 作为产物：
  描述：

  氘代甲醇 、 烯丙基苯乙基醚 在 喹哪啶酸 、 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 作用下， 以99.6%的产率得到1-(trideuteriomethoxy)prop-2-ene
  参考文献：
  名称：

  CpRuIIPF6 /喹啉酸催化的化学选择性烯丙基醚裂解。一种简单实用的羟基脱保护方法。

  摘要：

  阳离子CpRu（II）配合物与奎宁酸组合显示出高反应活性和化学选择性，可催化脱保护作为烯丙基醚的羟基。该催化剂在醇溶剂中操作，不需要任何其他亲核试剂，满足了操作简便，安全和环境友好的实际要求。该脱保护策略对包括肽和核苷在内的多种多功能分子的广泛应用，可能在保护基化学中提供新的机会。[结构：见文字]

  DOI：

  10.1021/ol0493397

文献信息

• Pathways of decomposition of N-cyclopropyl N nitrosoureas in methanol
  作者：I. P. Klimenko、Yu. V. Tomilov

  DOI：10.1007/s11172-005-0260-1

  日期：2005.2

  Decomposition of a series of N-cyclopropyl-N-nitrosoureas (CNU) in CD3OD was studied. These decompose much more rapidly than N-methyl-N-nitrosourea, one of the decomposition pathways being denitrosation, which is atypical of alkylnitrosoureas under the reaction conditions used. The nature of substituents in the cyclopropane ring has a great effect on the stability of CNU and the product ratio. In the presence of H2 SO4, decomposition occurs much more rapidly. Possible pathways of the formation of the major decomposition products of CNU are proposed based on the experimental data.

  对一系列N-环丙基-N-亚硝基脲（CNU）在CD3OD中的降解进行了研究。它们的降解速度远快于N-甲基-N-亚硝基脲，其中一个降解途径是脱亚硝基化，这在所用反应条件下对烷基亚硝基脲而言是不典型的。环丙烷环中取代基的性质对CNU的稳定性和产物比具有很大影响。在H2SO4存在下，降解速度大大加快。根据实验数据，提出了CNU主要降解产物形成的可能途径。
• Raman spectroscopic study of allyl methyl ether (3-methoxy-1-propene), CH2CHCH2OCH3, and some isotopically labelled analogues
  作者：R.D. Bowen、H.G.M. Edwards、D.W. Farwell

  DOI：10.1016/0022-2860(95)08852-m

  日期：1995.6

  Abstract Fourier-transform Raman spectra of allyl methyl ether, CH 2 CHCH 2 OCH 3 , three deuterated derivatives and one 13 C derivative have been obtained. Comparison of the spectra of the deuterated and protiated compounds in conjunction with polarization data has enabled full vibrational assignments to be made for the carbon-hydrogen modes and the 13 C data have identified some skeletal modes of

  摘要 获得了烯丙基甲基醚、CH 2 CHCH 2 OCH 3 、三种氘代衍生物和一种13 C衍生物的傅里叶变换拉曼光谱。氘化和质子化化合物的光谱与极化数据的比较使得能够对碳氢模式进行完整的振动分配，并且 13 C 数据已经确定了 CO 和 CC 键的一些骨架模式。由于从氘代化合物中获得的数据，特别是对一些初步建议进行了修订，以对生物学感兴趣的分子进行暂定文献分配。在其他情况下，已确认现有分配。
• Unimolecular reactions of ionized methyl allyl ether
  作者：Richard D. Bowen、Andrew D. Wright、Peter J. Derrick

  DOI：10.1002/oms.1210270812

  日期：1992.8

  AbstractThe fragmentation of CH2CHCH2OCH3+· cation‐radicals has been investigated by means of 2H‐ and 13C‐labelling experiments and by analysis of collision‐induced dissociation spectra. Metastable C4H8O+· species decompose via one of three main channels which involve loss of (a) a hydrogen atom, (b) a methyl radical or (c) a formaldehyde molecule. Extensive, but not complete, exchange of the hydrogen and deuterium atoms in specifically labelled C4H8‐nDnO+· analogues precedes each of the three fragmentation pathways. The role of distonic ions in the rearrangement steps which bring about hydrogen exchange is discussed. The influence of isotope effects on the relative rates of the major reactions and the associated kinetic energy releases is examined. Only loss of a hydrogen atom is subject to a substantial isotope effect. Elimination of a methyl radical releases a large amount of kinetic energy, as is shown by the broad and dish‐topped appearance of the corresponding metastable peak (T1/2 ≈ 42 kJ mol−1). The carbon atom of the original methoxy group is specifically expelled in this process. Both the large T1/2 value and the unusual site selectivity are atypical of methyl and other alkyl radical losses from ionized alkenyl methyl ethers. The carbon atom of the methoxy group also participates specifically in formaldehyde elimination, but the two hydrogen atoms are not always selected from the three contained in the initial methoxy group. The implications of these labelling results for the synchronicity of concert of formaldehyde loss, which can be formu lated as a pericyclic process, is analysed.
• Halide-Free Dehydrative Allylation Using Allylic Alcohols Promoted by a Palladium−Triphenyl Phosphite Catalyst
  作者：Yoshihito Kayaki、Takashi Koda、Takao Ikariya

  DOI：10.1021/jo030370g

  日期：2004.4.1

  The triphenyl phosphite-palladium complex was found to effect catalytic substitution reactions of allylic alcohols via a direct C-O bond cleavage. The dehydrative etherification proceeded efficiently without any cocatalysts and bases to give allylic ethers in good to excellent yields.