(1SR,2SR,3SR)-2,3-dihydroxycyclohexyl acetate | 4516-83-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1SR,2SR,3SR)-2,3-dihydroxycyclohexyl acetate
• 英文别名: [(1R,2R,3R)-2,3-dihydroxycyclohexyl] acetate
• CAS: 4516-83-0
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: PWBFTKWRAXFTLR-BWZBUEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1SR,2SR,3SR)-2,3-dihydroxycyclohexyl acetate 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 (1RS,2SR)-2-hydroxy-3-oxocyclohexyl acetate
  参考文献：
  名称：

  Regioselective oxidation of azidodiols, bromodiols and triol derivatives by dimethyldioxirane

  摘要：

  Azidodiols, bromodiols and triol derivatives were regioselectively monooxidised to the corresponding ketols using dimethyldioxirane. This regioselectivity is essentially determined by dipolar functionalities close to the potential reactive carbinol. These results make the reactivity of polyols with dimethyldioxirane highly predictable. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00885-0
• 作为产物：
  描述：

  3-乙酰氧基环己烯 在 potassium permanganate 、 双氧水 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以83%的产率得到(1SR,2SR,3SR)-2,3-dihydroxycyclohexyl acetate
  参考文献：
  名称：

  A facile synthesis of vicinal cis-diols from olefins catalyzed by in situ generated Mn_xO_y nanoaggregates

  摘要：

  在烯烃合成邻二醇的过程中，主要是通过KMnO₄/H₂O₂在原位生成MnxOy氧化物衍生物，主要是Mn₃O₄纳米聚集体。

  DOI：

  10.1039/c5ra01646k

文献信息

• The acid accelerated ruthenium-catalysed dihydroxylation. Scope and limitations
  作者：Bernd Plietker、Meike Niggemann、Anja Pollrich

  DOI：10.1039/b316546a

  日期：——

  Recently, we discovered a significant rate acceleration in RuO4-catalysed dihydroxylations of olefins by addition of Brönsted-acids resulting in a reduction of the catalyst loading to only 0.5 mol%. The present paper gives a full account on the optimisation protocol that led to the discovery of the beneficial influence of protic acids. A strong focus is set on the detailed description of the influence of different reaction parameters on both reactivity and selectivity. In the second part an intense investigation of scope and limitations will be presented. The results provided in this manuscript might lead to a deeper understanding of competing processes that influence the selectivity in RuO4-catalysed dihydroxylations.

  最近，我们发现在烯烃双羟基化反应中，通过添加布朗斯台德酸，RuO4催化的反应速率显著加快，并且催化剂负载量降低至仅0.5摩尔%。本文详细阐述了优化程序，揭示了质子酸的有益影响，并着重描述了不同反应参数对反应活性和选择性的影响。在第二部分，将展示对范围和限制的深入研究。本文提供的结果可能有助于更深入地理解影响RuO4催化双羟基化反应选择性的竞争过程。
• On stereochemistry of osmium tetraoxide oxidation of allylic alcohol systems. Empirical rule
  作者：J.K. Cha、W.J. Christ、Y. Kishi

  DOI：10.1016/0040-4020(84)80008-3

  日期：1984.1

  An empirical formulation is presented to predict the stereochemistry of major osmylation products of allylic alcohols and their derivatives.

  提出了一种经验公式来预测烯丙基醇及其衍生物的主要渗透作用产物的立体化学。
• Regioselective Ring-Opening of 2,3-Epoxy Alcohols with Tetramethylammonium Triacetoxyborohydride
  作者：Toshio Honda、Hirotake Mizutani

  DOI：10.3987/com-98-8263

  日期：——

  Treatment of 2,3-epoxy alcohols with tetramethylammonium triacetoxyborohydride afforded the ring-opening products at the C-3 position, regioselectively, where the presence of Me4NBH(OAc)(3) increased the reaction rate and regioselectivity by forming the chelation intermediate between the metal center and the epoxy alcohol oxygens.
• Shing, Tony K. M.; Tai, Vincent W.-F.; Tam, Eric K. W., Angewandte Chemie, 1994, vol. 106, # 22, p. 2408 - 2409
  作者：Shing, Tony K. M.、Tai, Vincent W.-F.、Tam, Eric K. W.

  DOI：——

  日期：——