(2S,5R)-2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran | 105814-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2S,5R)-2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran
• 英文别名: 2-[(2S,5R)-5-methyloxolan-2-yl]propan-2-ol
• CAS: 105814-93-5
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: GDFJZYRQAYBNLM-RQJHMYQMSA-N

物化性质

• 沸点：
  195.6±8.0 °C(Predicted)
• 密度：
  0.981±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,5R)-2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran 在 2,6-二甲基吡啶 、 rhenium(VII) oxide 作用下， 生成 丙酮 、 γ-戊内酯
  参考文献：
  名称：

  Directed oxidative cyclization of 5-hydroxyalkenes with rhenium oxide

  摘要：

  5-Hydroxyalkenes react with rhenium(VII) oxide (Re2O7) to provide 2-hydroxymethyltetrahydrofurans. Oxidative cyclization occurs with overall syn addition to the alkenes in moderate yields with little tendency toward oxidation of alcohols to carbonyl compounds.

  DOI：

  10.1016/0040-4039(92)80010-h
• 作为产物：
  描述：

  6-甲基-5-庚烯-2-醇 在 Ru2(CO)4(μ-H)(C4Ph4COHOCC4Ph4) Candida antarctica lipase B 、 四溴化碳 、 Rhodococcus ruber DSM 44540 、 Tris buffer 、 硫酸 、 potassium carbonate 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 121.5h， 生成 (2S,5R)-2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran
  参考文献：
  名称：

  Enantio- and diastereo-convergent synthesis of (2R,5R)- and (2R,5S)-Pityol through enzyme-triggered ring closure

  摘要：

  A short chemoenzymatic synthesis of the (2R,5S)- and (2R,5R)-stereoisomer of the bark beetle pheromone Pityol 1 was achieved from (+/-)-Sulcatol 2 in an enantio- and diastereo-convergent fashion without the formation of any 'unwanted' stereoisomer. The key steps include: (i) lipase-catalyzed deracemization of (+/-)-2 using kinetic resolution coupled to an in-situ inversion or alternatively, dynamic resolution using combined lipase- and Ru-catalysis: and (ii) creation of the second stereogenic center by an epoxide hydrolase-catalyzed diastereo-convergent hydrolysis of a haloalkyl oxirane, followed by spontaneous ring Closure to form 1 in a stereoselective fashion. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00370-6

文献信息

• Diastereoselective Titanocene-Catalyzed Oxidative Cyclization of Bishomoallylic Alcohols
  作者：Alessandra Lattanzi、Giorgio Della Sala、Maurizio Russo、Arrigo Scettri

  DOI：10.1055/s-2001-16779

  日期：——

  Bishomoallylic alcohols are converted in good yields and diastereoselectivity into tetrahydrofuranols and tetrahydropyranols by Cp2TiCl2/t-butyl hydroperoxide/activated 4 Å molecular sieves system.

  Bishomo醇在Cp2TiCl2/t-丁基过氧化氢/活化的4 Å分子筛体系中以良好的产率和立体选择性转化为四氢呋喃醇和四氢吡喃醇。
• Stereoselective reduction of acetals. A method for reductive generation of heterocyclic ring systems
  作者：Kazuaki Ishihara、Atsunori Mori、Hisashi Yamamoto

  DOI：10.1016/s0040-4020(01)85584-8

  日期：1990.1

  A new synthetic process for the construction of oxygen-containing heterocyclic systems starting from bicyclic acetals is described. We have investigated the mechanism and the stereochemical course of the reductive cleavage of acetals.

  描述了一种新的合成方法，用于从双环缩醛开始构建含氧杂环系统。我们已经研究了乙缩醛还原裂解的机理和立体化学过程。
• Stereocontrolled oxidation of 5-hydroxyalkenes with rhenium oxide. III
  作者：Suhan Tang、Robert M. Kennedy

  DOI：10.1016/s0040-4039(00)79077-0

  日期：1992.9

  5-Hydroxyalkenes react with rhenium (VII) oxide (Re2O7) to provide 2-hydroxymethyl-tetrahydrofurans. Oxidation occurs with overall syn addition to the alkene. Stereoselectivity is easily understood by invoking [2+2] cycloaddition followed by reductive elimination.

  5-羟基烯烃与氧化（（Re 2 O 7）反应，生成2-羟甲基-四氢呋喃。氧化与烯烃的全部合成物加成一起发生。通过调用[2 + 2]环加成，然后进行还原性消除，可以轻松理解立体选择性。
• Enzyme-triggered opening of an epoxide: Chemoenzymatic synthesis of (2R,5R)- and (2S,5R)-pityol
  作者：Martin Mischitz、Alexandra Hackinger、Iris Francesconi、Kurt Faber

  DOI：10.1016/s0040-4020(01)85340-0

  日期：1994.1

  Treatment of a diastereomeric mixture of (±)-epoxy-ester 1 with a crude immobilised enzyme preparation (Novo SP 409) or whole lyophilized cells of Rhodococcus erythropolis NCIB 11540 in aqueous buffer (pH 7.0) did not lead to the formation of the expected epoxy alcohol 2 or diol 5 but surprisingly furnished the rearranged products 4a and 4b in >98% enantiomeric excess. (2R*,5R*)-2-(1-Hydroxy- 1 -m

  用粗制的固定化酶制剂（Novo SP 409）或红球红球菌NCIB 11540的冻干全细胞在水性缓冲液（pH 7.0）中处理（±）-环氧酯1的非对映混合物环氧醇2或二醇5，但出人意料的是提供的重排产物4a和4b对映体过量> 98％。（2 R *，5 R *）-2-（1-羟基-1-甲基乙基）-5-甲基四氢呋喃（pityol，4a）是榆树皮甲虫Pteleobius vittatus的信息素。苯甲醇不是由环氧酒精形成的事实2 在没有生物催化剂的情况下，我们得出的结论是重排是由酶触发的。
• Stereoselective reduction of bicyclic acetals. A method for reductive generation of heterocyclic ring systems
  作者：Kazuaki Ishihara、Atsunori Mori、Hisashi Yamamoto

  DOI：10.1016/s0040-4039(00)96927-2

  日期：——