3-chloro-1,1-dideuteriopropanol | 21045-91-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-chloro-1,1-dideuteriopropanol
• 英文别名: 3-chloro-1,1-dideuterio-propan-1-ol；3-Chlor-1,1-dideutero-propanol；3-Chlor-(1,1-D2)-propanol-(1)；3-Chlor-propanol-(1)-d2-(1,1)；3-Chlor-1-propanol-1,1-d(2)；3-chloro-1,1-dideuteriopropan-1-ol
• CAS: 21045-91-0
• 化学式: C₃H₇ClO
• 分子量: 96.5251
• InChiKey: LAMUXTNQCICZQX-SMZGMGDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  5.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-chloro-1,1-dideuteriopropanol 、 乙酰氯 生成 <3-Chlor-1-dideutero-propyl>-acetat
  参考文献：
  名称：

  Chemical ionization mass spectra of selected C3H6O compounds

  摘要：

  AbstractThe chemical ionization mass spectra of five isomers of C3H6O (acetone, propionaldehyde, oxetane, propylene oxide and allyl alcohol) have been determined using a variety of reagent gases (H2, D2, N2/H2, CO2/H2 and CO/H2). The [C3H7O]+ ions produced by protonation of these isomers undergo very similar reactions to those reported for analogous [C3H7O]+ metastable ions; however, decomposing ions generated by chemical ionization appear to have somewhat higher internal energies. The results of 2H labelling studies (D2 reagent gas or labelled analogues of C3H6O) indicate that protonation occurs mainly on oxygen and are consistent with previous investigations of metastable oxonium ions. The protonated acetone ion is particularly stable, in agreement with the higher activation energies for fragmentation of this isomer than for other [C3H7O]+ structures. As the calculated heat of protonation of C3H6O is reduced by changing the reagent gas, so the extent to which fragmentation occurs decreases. This is discussed in the context of competition between fragmentation and collisional stabilization of the excited [C3H7O]+* ion. It is concluded that on average a large fraction (approaching 1) of the exothermicity of the protonation reaction resides in the [C3H7O]+* ions produced initially.

  DOI：

  10.1002/oms.1210160404
• 作为产物：
  描述：

  3-氯丙酸甲酯 在 lithium aluminium deuteride 作用下， 以 乙醚 为溶剂， 生成 3-chloro-1,1-dideuteriopropanol
  参考文献：
  名称：

  Chemical ionization mass spectra of selected C3H6O compounds

  摘要：

  AbstractThe chemical ionization mass spectra of five isomers of C3H6O (acetone, propionaldehyde, oxetane, propylene oxide and allyl alcohol) have been determined using a variety of reagent gases (H2, D2, N2/H2, CO2/H2 and CO/H2). The [C3H7O]+ ions produced by protonation of these isomers undergo very similar reactions to those reported for analogous [C3H7O]+ metastable ions; however, decomposing ions generated by chemical ionization appear to have somewhat higher internal energies. The results of 2H labelling studies (D2 reagent gas or labelled analogues of C3H6O) indicate that protonation occurs mainly on oxygen and are consistent with previous investigations of metastable oxonium ions. The protonated acetone ion is particularly stable, in agreement with the higher activation energies for fragmentation of this isomer than for other [C3H7O]+ structures. As the calculated heat of protonation of C3H6O is reduced by changing the reagent gas, so the extent to which fragmentation occurs decreases. This is discussed in the context of competition between fragmentation and collisional stabilization of the excited [C3H7O]+* ion. It is concluded that on average a large fraction (approaching 1) of the exothermicity of the protonation reaction resides in the [C3H7O]+* ions produced initially.

  DOI：

  10.1002/oms.1210160404

文献信息

• Synthesis of L-ornithines stereospecifically deuterated at C-3
  作者：Jack E. Baldwin、Kirsten D. Merritt、Christopher J. Schofield

  DOI：10.1016/s0040-4039(00)79263-x

  日期：1993.6

  (2S, 3S)-[2,3-H-2(2)]-Ornithine and (2S, 3R)-[3-H-2(1)]-ornithine were prepared with high stereoselectivity via asymmetric reduction catalysed by bicyclo[2.2.1]hepta-2,5-diene}(R)-1,2-bis(diphenylphosphino)propane}rhodium (1) trifluoromethanesulphonate [(R)-Rh-Prophos].

  通过(Rh)-Rh-Prophos催化的不对称还原反应，以高立体选择性制备了(2S, 3S)-[2,3-H-2(2)]-鸟氨酸和(2S, 3R)-[3-H-2(1)]-鸟氨酸。
• Reductive Deuteration of Acyl Chlorides for the Synthesis of α,α-Dideuterio Alcohols Using SmI2 and D2O
  作者：Hengzhao Li、Yuxia Hou、Mengqi Peng、Lijun Wang、Junyu Li、Lei Ning、Zemin Lai、Yixuan Li、Jie An

  DOI：10.3390/molecules28010416

  日期：——

  The synthesis of α,α-dideuterio alcohols has been achieved via single electron transfer reductive deuteration of acyl chlorides using SmI2 and D2O. This method is distinguished by its remarkable functional group tolerance and exquisite deuterium incorporation, which has also been applied to the synthesis of valuable deuterated agrochemicals and their building blocks.

  α,α-二氘醇的合成是通过使用 SmI2 和 D2O 对酰氯进行单电子转移还原氘化来实现的。该方法以其卓越的官能团耐受性和精细的氘掺入而著称，也已应用于合成有价值的氘代农用化学品及其结构单元。
• Synthesis of chirally deuteriated phthalimido-propanols and evaluation of their absolute stereochemistry
  作者：P. C. Prabhakaran、Steven J. Gould、Gary R. Orr、James K. Coward

  DOI：10.1021/ja00225a032

  日期：1988.8
• MAERCKER, ADALBERT;STOTZEL, REINHARD, CHEM. BER., 120,(1987) N 10, 1695-1706
  作者：MAERCKER, ADALBERT、STOTZEL, REINHARD

  DOI：——

  日期：——
• PRABHAKARAN, P. C.;GOULD, STEVEN J.;ORR, GARY R.;COWARD, JAMES K., J. AMER. CHEM. SOC., 110,(1988) N 17, C. 5779-5784
  作者：PRABHAKARAN, P. C.、GOULD, STEVEN J.、ORR, GARY R.、COWARD, JAMES K.

  DOI：——

  日期：——