碘代丙烷-D3 | 25493-16-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 中文名称: 碘代丙烷-D3
• 英文名称: <3,3,3-2H3>-1-iodopropane
• 英文别名: [²H₃]-propyl bromide；Propyljodid-3,3,3-d2；1-Iod-3,3,3-trideutero-propan；1,1,1-trideuterio-3-iodo-propane；1-Iodopropane-3,3,3-D3；1,1,1-trideuterio-3-iodopropane
• CAS: 25493-16-7
• 化学式: C₃H₇I
• 分子量: 172.969
• InChiKey: PVWOIHVRPOBWPI-FIBGUPNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  4
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  碘代丙烷-D3 、 异丙醇 在 sodium hydride 作用下， 生成 isopropyl <3,3,3-2H3>propyl ether
  参考文献：
  名称：

  Mechanism of propene and water elimination from the oxonium ion CH₃CHO⁺CH₂CH₂CH₃

  摘要：

  The site-selectivity in the hydrogen transfer step(s) which result in propene and water loss from metastable oxonium ions generated as CH3CH=O+CH2CH2CH3 have been investigated by deuterium-labelling experiments. Propene elimination proceeds predominantly by transfer of a hydrogen atom from the initial propyl-substituent to oxygen. However, the site-selectivity for this process is inconsistent with beta-hydrogen transfer involving a four-centre transition state. The preference for apparent alpha- or gamma-hydrogen transfer is interpreted by a mechanism in which the initial propyl cation accessible by stretching the appropriate bond in CH3CH=O+CH2CH2CH3 isomerizes unidirectionally to an isopropyl cation, which then undergoes proton abstraction-from either methyl group {CH3CH=O+CH2CH2CH3 --> CH3CH=O--- (CH2CH2CH3)-C-+ --> [CH3CH-O (CH)-C-+(CH3)(2)] --> [CH3CH=OH+ CH3CH=CH2]}. This mechanism involving ion-neutral complexes can be elaborated to accommodate the minor contribution of expulsion of propene containing hydrogen atoms originally located on the two-carbon chain. Water elimination resembles propene loss insofar as there is a strong preference for selecting the hydrogen atoms from the alpha- and gamma-positions of the initial propyl group. The bulk of water loss is explicable by an extension of the mechanism for propene loss, with the result that one hydrogen atom is eventually transferred to oxygen from each of the two methyl groups in the complex [CH3CH=O- (CH)-C-+(CH3)(2)]. This site-selectivity is strikingly different from that (almost random participation of the seven hydrogen atoms of the propyl substituent) encountered in the corresponding fragmentation of the lower homologue CH2O+CH2CH2CH(3). This contrast is explained in terms of the differences in the relative energetics and associated rates of the cation rearrangement and hydrogen transfer steps.

  DOI：

  10.1039/p29950000119
• 作为产物：
  描述：

  丙醇-D3 在 碘 作用下， 生成 碘代丙烷-D3
  参考文献：
  名称：

  Unimolecular reactions of isolated organic ions: The chemistry of the oxonium ions CH3CH2CH2CH2+O = CH2 and CH3CH2CH2CH = O+CH3

  摘要：

  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.

  DOI：

  10.1002/oms.1210281035

文献信息

• Key Odor-Active Compounds in Raw Green and Red <i>Toona sinensis</i> (A. Juss.) Roem. and Their Changes during Blanching
  作者：Xiaoting Zhai、Michael Granvogl

  DOI：10.1021/acs.jafc.0c02012

  日期：2020.7.8

  (E,Z)- and (Z,Z)-di-1-propenyl trisulfide, 2-methoxyphenol, and 4-ethylphenol were first identified as key odorants of T. sinensis. Clear differences between green and red T. sinensis in aroma profiles, flavor dilution factors, quantitative data, and odor activity values verified that (E,E)-, (E,Z)-, and (Z,Z)-di-1-propenyl disulfide, (E,E)-, (E,Z)- and (Z,Z)-di-1-propenyl trisulfide, cis- and trans-2-mercapto-3

  芳香提取物稀释分析和顶空香气稀释分析中的应用揭示生绿51种气味剂香椿和54种气味物质在生红香椿在8-4096风味稀释因子范围。（E，E）-2,4-癸二醛，壬醛，2,3,5-三甲基吡嗪，（E，Z）-和（Z，Z）-二-1-丙烯基三硫化物，2-甲氧基苯酚和4-乙基苯酚被首次确定为中华T的关键气味。绿色和红色中华丁香在香气特征，风味稀释因子，定量数据和气味活性值之间的明显差异证实了（E，（E）-，（E，Z）-和（Z，Z）-di-1-丙烯基二硫化物，（E，E）-，（E，Z）-和（Z，Z）-di-1-丙烯基三硫化物，顺式和反式-2-巯基3,4-二甲基-2,3-二氢噻吩和二甲基硫醚引起每个品种的明显硫磺味。此外，己醛，（E）-2-己烯醛，（E）-2-己烯-1-醇和（E，Z）-2,6-壬二烯醛导致绿色丁香中产生绿色气味。2-甲氧基苯酚和4-乙基苯酚有助于红色中华T的强烈酚类香气。变白中华绒螯蟹的定量实验和