碘代丙烷-D2 | 25493-14-5

• 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-D2
• 英文名称: 1-iodo<1,1-2H2>propane
• 英文别名: Propyljodid-1,1-d2；1-Iod-1,1-dideuterio-propan；1-Iod-1,1-dideutero-propan；n-Propyliodid-1,1-d2；1,1-dideuterio-1-iodo-propane；1-Iodopropane-1,1-D2；1,1-dideuterio-1-iodopropane
• CAS: 25493-14-5
• 化学式: C₃H₇I
• 分子量: 171.977
• InChiKey: PVWOIHVRPOBWPI-SMZGMGDZSA-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：

  1,1-二氘代-2-丙烯醇 、 碘代丙烷-D2 在 sodium hydride 作用下， 生成 <1,1-2H2>allyl <1,1-2H2>-1-propyl ether
  参考文献：
  名称：

  Bowen, Richard D.; Wright, Andrew D.; Derrick, Peter J., Journal of the Chemical Society. Perkin transactions II, 1993, # 3, p. 501 - 507

  摘要：

  DOI：
• 作为产物：
  描述：

  丙醇-D2 在 磷化氢 、 碘 作用下， 生成 碘代丙烷-D2
  参考文献：
  名称：

  Bowen, Richard D.; Derrick, Peter J., Journal of the Chemical Society. Perkin transactions II, 1992, # 7, p. 1041 - 1047

  摘要：

  DOI：

文献信息

• Bowen, Richard D.; Derrick, Peter J., Journal of the Chemical Society. Perkin transactions II, 1992, # 7, p. 1041 - 1047
  作者：Bowen, Richard D.、Derrick, Peter J.

  DOI：——

  日期：——
• Mass spectrometry in structural and stereochemical problems. CLXXX. Study of the effect of ring size in reciprocal hydrogen transfer
  作者：George Eadon、Carl Djerassi

  DOI：10.1021/ja01038a052

  日期：1969.5
• Bowen, Richard D.; Wright, Andrew D.; Derrick, Peter J., Journal of the Chemical Society. Perkin transactions II, 1993, # 3, p. 501 - 507
  作者：Bowen, Richard D.、Wright, Andrew D.、Derrick, Peter J.

  DOI：——

  日期：——
• Mechanism of propene and water elimination from the oxonium ion CH₃CHO⁺CH₂CH₂CH₃
  作者：Richard D. Bowen、Dennis Suh、Johan K. Terlouw

  DOI：10.1039/p29950000119

  日期：——

  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.