(2R,3S)-2-deuterio-3-hexanol | 89321-79-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S)-2-deuterio-3-hexanol
• CAS: 89321-79-9
• 化学式: C₆H₁₄O
• 分子量: 103.169
• InChiKey: ZOCHHNOQQHDWHG-WMMFQUQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  7.0
• 可旋转键数：
  3.0
• 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：

  (2R,3S)-2-deuterio-3-hexanol 在 chromium(VI) oxide 、 Celite 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (2R)-2-deuterio-3-hexanone
  参考文献：
  名称：

  Optical rotatory dispersion studies. 137. Synthesis and chiroptical properties of .alpha.- and .beta.-deuterium substituted aliphatic aldehydes and ketones

  摘要：

  DOI：

  10.1021/jo00183a007
• 作为产物：
  描述：

  在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.5h， 生成 (2R,3S)-2-deuterio-3-hexanol
  参考文献：
  名称：

  Optical rotatory dispersion studies. 137. Synthesis and chiroptical properties of .alpha.- and .beta.-deuterium substituted aliphatic aldehydes and ketones

  摘要：

  DOI：

  10.1021/jo00183a007

文献信息

• Stereochemical Preferences in 4-Center <i>Syn-</i>Eliminations from Gaseous Ions
  作者：Tangyuan Cao、Michael K. Nguyen、Scott V. Serafin、Thomas Hellman Morton

  DOI：10.1021/jo800658g

  日期：2008.8.1

  Concerted unimolecular eliminations from ionized sec-alkyl aryl ethers (ROAr(+center dot)) display a preference for producing double bonds with trans geometry. This preference can be assessed quantitatively, provided that a regioselective variant can be found. Expulsion of neutral alkenes via syn-elimination to give ionized ArOH does not exhibit a pronounced preference with regard to the direction of elimination. By contrast, ionized 2-hexyl p-trifluoromethylphenyl ether eliminates neutral ArOH regioselectively, giving ionized 2-hexenes rather than ionized 1-hexene. Vicinally monodeuterated 2-hexyl and 3-hexyl ethers were prepared as pure diastereomers. Metastable ion decompositions of their gaseous radical cations are compared over two different time windows. The regioselectivity for the 2-hexyl ether allows the geometric preference for the double bonds to be estimated based on the difference between the erythro and threo monodeuterated diastereomers (trans/cis = 2.0 for producing ionized 2-hexene from parent ions with the lowest internal energies). The 3-hexyl ethers and ionized 2- and 3-phenoxyoctanes also undergo stereoselective elimination but give experimental values that reflect their lack of regioselectivity. Examination of erythro/threo combinations shows that GC/MS/MS has the ability to quantitate stereochemistry in mixtures containing both positional and stereoisomers.