alpha deuteriated decyl alcohol | 133827-65-3

• 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: alpha deuteriated decyl alcohol
• 英文别名: decan-1-ol-1-d；1-deuteriodecanol；Deuterodecanol；1-deuteriodecan-1-ol
• CAS: 133827-65-3
• 化学式: C₁₀H₂₂O
• 分子量: 159.276
• InChiKey: MWKFXSUHUHTGQN-MMIHMFRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  11
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  alpha deuteriated decyl alcohol 在 氯化亚砜 作用下， 以 吡啶 为溶剂， 生成 deuteriated decyl chloride
  参考文献：
  名称：

  Nicoletta, Fiore Pasquale; Golemme, Attilio; Picci, Nevio, Gazzetta Chimica Italiana, 1996, vol. 126, # 5, p. 279 - 284

  摘要：

  DOI：
• 作为产物：
  描述：

  癸醛 在 锰 、 2,4,6-collidine deuterochloride 、 重水 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到alpha deuteriated decyl alcohol
  参考文献：
  名称：

  Mn(0)-Mediated Chemoselective Reduction of Aldehydes. Application to the Synthesis of α-Deuterioalcohols

  摘要：

  A mild simple safe chemoselective reduction of different kinds to the corresponding alcohols mediated by the Mn dust/water system is described. In addition to this, the use of D2O leads to the synthesis of alpha-deuerated alcohols and constitutes an efficient inexpensive alternative for the preparation of these compounds.

  DOI：

  10.1021/jo1015618

文献信息

• Mechanistic study of the rhodium(I)-catalyzed hydroboration reaction
  作者：David A. Evans、Gregory C. Fu、Benjamin A. Anderson

  DOI：10.1021/ja00043a010

  日期：1992.8

  The objective of this study has been to elucidate the mechanism of the rhodium(I)-catalyzed hydroboration process. Evidence that the reaction proceeds through a multistep pathway analogous to that of transition metal catalyzed olefin hydrogenation is presented. Deuterium labeling experiments reveal reversible elementary steps in the catalytic cycle; the level of reversibility is found to be substrate-dependent

  本研究的目的是阐明铑（I）催化的硼氢化过程的机理。提供了该反应通过类似于过渡金属催化的烯烃氢化的多步途径进行的证据。氘标记实验揭示了催化循环中可逆的基本步骤；发现可逆性水平取决于底物。通过与外来氧化剂接触造成的催化剂污染对反应有显着影响，并且似乎是涉及产品区域选择和氘标记实验的报告差异的来源
• The rhodium-catalyzed hydroboration of olefins: a mechanistic investigation
  作者：David A. Evans、Gregory C. Fu

  DOI：10.1021/jo00295a007

  日期：1990.4
• Accessing Z‐Enynes via Cobalt‐Catalyzed Propargylic Dehydrogenation
  作者：Alexandra K. Bodnar、Timothy R. Newhouse

  DOI：10.1002/anie.202402638

  日期：2024.6.21

  Alkenes constitute an enabling motif in organic synthesis, as they can be functionalized to form highly substituted molecules. Z‐alkenes are generally challenging to access due to the thermodynamic preference for the formation of E‐alkenes compared to Z‐alkenes. Dehydrogenation methodologies to selectively form Z‐alkenes have not yet been reported. Herein, we report a Z‐selective, propargylic dehydrogenation that provides 1,3‐enynes through the invention of a Co‐catalyzed oxidation system. Observation of a kinetic isotope effect (KIE) revealed that deprotonation of the propargylic position is the rate limiting step. Additionally, isomerization experiments were conducted and confirmed that the observed Z‐selectivity is a kinetic effect. A proposed stereomechanistic model for the Z‐selectivity is included.