3,4-Epoxypentan-2-ol | 22520-29-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-Epoxypentan-2-ol
• CAS: 22520-29-2
• 化学式: C₅H₁₀O₂
• 分子量: 102.13
• InChiKey: FHIKGRJBSRFOJT-WISUUJSJSA-N

物化性质

• 沸点：
  164.7±8.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-戊烯-2-醇 在 titanium(IV) isopropylate 、 C₂₀H₃₈O₈ 、 过氧化氢异丙苯 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 3,4-Epoxypentan-2-ol 、 (S)-3-penten-2-ol
  参考文献：
  名称：

  An optimised and recoverable tartrate surrogate for sharpless asymmetric epoxidations

  摘要：

  The tetrahydroxy diester 7d (R = Pr-i) is almost as effective as diisopropyl tartrate in SAE reactions of (E)-allylic alcohols and can be recovered and re-used following a relatively simple work-LIP procedure. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.069

文献信息

• Regio-, Diastereo-, and Chemoselectivities in the Dioxirane Oxidation of Acyclic and Cyclic Allylic Alcohols by Methyl(trifluoromethyl)dioxirane (TFD): A Comparison with Dimethyldioxirane
  作者：Waldemar Adam、Rodrigo Paredes、Alexander K. Smerz、L. Angela Valoza

  DOI：10.1002/(sici)1099-0690(199802)1998:2<349::aid-ejoc349>3.0.co;2-r

  日期：1998.2

  regioselectivity of the geraniol epoxidation by methyl(trifluoromethyl)dioxirane (TFD) reveals that as for the less reactive dimethyldioxirane (DMD), hydrogen bonding stabilizes the transition state of the epoxidation. In protic media, the hydrogen bonding is exerted intermolecularly by the solvent, whereas in unpolar, non-hydrogen-bonding solvents intramolecular assistance through the adjacent hydroxy

  甲基（三氟甲基）二环氧乙烷（TFD）对香叶醇环氧化的区域选择性的溶剂依赖性变化表明，对于反应性较低的二甲基二环氧乙烷（DMD），氢键稳定了环氧化的过渡态。在质子介质中，氢键由溶剂在分子间施加，而在非极性，非氢键的溶剂中，通过相邻羟基官能团的分子内辅助起作用，并且有利于对烯丙基醇部分的攻击。对于手性烯丙基醇，另外的空间相互作用在构象固定的过渡态中控制π-面选择性。与DMD相似，TFD环氧化的氢键过渡态中的优选二面角约为130°，此处研究的1和3-5被TFD化学选择性环氧化而未形成相应的烯酮。
• Oxidation of allylic alcohols by dimethyldioxirane: Competition reaction between epoxidation and C-H insertion
  作者：Waldemar Adam、Frank Prechtl、Markus J. Richter、Alexander K. Smerz

  DOI：10.1016/s0040-4039(00)61350-3

  日期：1993.1

  Epoxidation of allylic alcohols with dimethyldioxirane is accompanied by oxidation of the hydroxy functionality; thus enone formation increases with decreasing substitution at the C-C double bond; nonetheless, selective epoxidation can be obtained by acylation of the alcohol functionality.
• Adam, Waldemar; Mitchell, Catherine M., Angewandte Chemie, 1996, vol. 108, # 5, p. 578 - 581
  作者：Adam, Waldemar、Mitchell, Catherine M.

  DOI：——

  日期：——
• Solvent Effects in the Regio- and Diastereoselective Epoxidations of Acyclic Allylic Alcohols by Dimethyldioxirane:  Hydrogen Bonding as Evidence for a Dipolar Transition State
  作者：Waldemar Adam、Alexander K. Smerz

  DOI：10.1021/jo951984r

  日期：1996.1.1

  A mechanistically significant solvent effect is observed in the regioselectivity of the geraniol epoxidation by dimethyldioxirane. In hydrogen-bonding solvents (MeOH), the 6,7-epoxide is preferred over the 2,3-epoxide (74:26), which reveals that the more nucleophilic 6,7 double bond (the 2,3 double bond is inductively deactivated by the allylic hydroxy group) is preferentially attacked by the electrophilic dimethyldioxirane. In MeOH, both regioisomeric dipolar transition states are equally well stabilized by interaction through intermolecular hydrogen bonding with solvent molecules. In the nonpolar CCl4, intramolecular hydrogen bonding with the allylic hydroxy functionality favors attack at the 2,3 double bond and proportionally more 2,3-epoxide is formed. Similarly, also the pi-facial selectivity in the dimethyldioxirane epoxidation of methyl-substituted chiral acyclic allylic alcohols is controlled by intermolecular versus intramolecular hydrogen bonding. Thus, higher three selectivities are obtained in the nonpolar CCl4 by stabilization of the diastereomeric transition state with minimal allylic strain through intramolecular hydrogen bonding with the allylic hydroxy group. The geometry of the dipolar transition state for the dimethyldioxirane epoxidations is similar to that of m-CPBA, but with apparently a slightly larger (ca. 130 degrees) dihedral angle alpha to relieve 1,2-allylic strain.
• Kamata, Keigo; Hirano, Tomohisa; Kuzuya, Shinjiro, Journal of the American Chemical Society, 2009, vol. 131, p. 6997 - 7004
  作者：Kamata, Keigo、Hirano, Tomohisa、Kuzuya, Shinjiro、Mizuno, Noritaka

  DOI：——

  日期：——