(2-fluoro-1,1-dideuterio)ethanol | 148871-33-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (2-fluoro-1,1-dideuterio)ethanol
• 英文别名: 1,1-dideuterio-2-fluoroethanol
• CAS: 148871-33-4
• 化学式: C₂H₅FO
• 分子量: 66.0436
• InChiKey: GGDYAKVUZMZKRV-CBTSVUPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  4.0
• 可旋转键数：
  1.0
• 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：

  (2-fluoro-1,1-dideuterio)ethanol 在 重铬酸吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 [1-2H1]-Fluoroacetaldehyde
  参考文献：
  名称：

  Moss, Steven J.; Murphy, Cormac D.; Hamilton, John T. G., Chemical Communications, 2000, # 22, p. 2280 - 2282

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium fluoroacetate 在 lithium aluminium deuteride 作用下， 以 乙醚 为溶剂， 反应 48.0h， 生成 (2-fluoro-1,1-dideuterio)ethanol
  参考文献：
  名称：

  β-卤代乙醇底物作为半乳糖氧化酶自由基机制的探针

  摘要：

  已知在与羰基相邻的碳上具有卤素取代基的羰基自由基阴离子通过卤化物阴离子喷射快速重排。这种重排是单铜/酪氨酸自由基酶半乳糖氧化酶 (GOase) 催化机制中可能的酮基阴离子中间体的理想探针。GOase 对 β-氟-、β-氯-、β-溴-和 β-碘乙醇的转化，通过将酶捕获在催化失活的单电子还原形式中，导致酶的基于机制的失活。假设基于机制的失活和周转通过相同的反应中间体进行，此处报告的数据将底物氧化步骤（从底物到酶的两个电子转移）的可能机制缩小到两种相似的可能性。

  DOI：

  10.1021/ja9626695

文献信息

• Currie, Graeme J.; Bowie, John H.; Downard, Kevin M., Journal of the Chemical Society. Perkin transactions II, 1989, p. 1973 - 1980
  作者：Currie, Graeme J.、Bowie, John H.、Downard, Kevin M.、Sheldon, John C.

  DOI：——

  日期：——
• Naghipur, Ali; Ikonomou, Michael G.; Kebarle, Paul, Journal of the American Chemical Society, 1990, vol. 112, # 8, p. 3178 - 3187
  作者：Naghipur, Ali、Ikonomou, Michael G.、Kebarle, Paul、Lown, J. William

  DOI：——

  日期：——
• Formation of isomeric ethylenehalonium and α-haloethyl cations and the role of ion-neutral complexes in the decomposition of protonated β-haloethanols
  作者：Albert J. R. Heck、Leo J. de Koning、Nico M. M. Nibbering

  DOI：10.1002/oms.1210280317

  日期：1993.3

  AbstractDecomposition of protonated β‐haloethanols was found to proceed predominantly via the loss of water. The mechanism was studied in the decomposition of metastable and collisionally activated isotopically labelled protonated β‐haloethanols. The study involved the characterization of the resulting fragment ions by collisionally activated decomposition and by low‐pressure ion/molecule probe reactions. The results indicate that loss of water from protonated β‐haloethanols proceeds via two competing mechanisms. The competition between these mechanisms appears to be governed by the nature of the halogen and by the internal energy of the decomposing protonated β‐haloethanol. In the first mechanism, loss of water is considered to be initiated by a concerted 1,2‐elimination of H3O+ resulting in an ion–molecule complex between H3O+ and haloethene. Rapid and reversible proton transfers between the two species in the complex is followed by a relatively slow dissociation ofthe intermediate complex resulting in the formation of an water molecule and an α‐haloethyl cation. In competition with this mechanism, loss of water can be initiated by carbon–oxygen bond cleavage, which is assisted by halogen–carbon bond formation resulting in the formation of a water molecule and cyclic ethylenehalonium ion.
• NAGHIPUR, ALI;IKONOMOU, MICHAEL G.;KEBARLE, PAUL;LOWN, J. WILLIAM, J. AMER. CHEM. SOC., 112,(1990) N, C. 3178-3187
  作者：NAGHIPUR, ALI、IKONOMOU, MICHAEL G.、KEBARLE, PAUL、LOWN, J. WILLIAM

  DOI：——

  日期：——