(1R)-1-[(2S)-oxolan-2-yl]hexan-1-ol | 68480-13-7

• 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: (1R)-1-[(2S)-oxolan-2-yl]hexan-1-ol
• CAS: 68480-13-7；143493-19-0；143264-37-3
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: SZXJOXHALDXHPQ-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(2S)-oxolan-2-yl]hexan-1-ol 在 potassium peroxymonosulfate 、 三氟甲磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 34.0h， 生成
  参考文献：
  名称：

  Acid-Catalyzed Regioselective Sulfetherification of Alkenols and Stereoselective Rearrangement of Tetrahydrofuran to Tetrahydropyran

  摘要：

  An efficient acid-catalyzed sulfetherification of various unsaturated alcohols with sulfenamides to form tetrahydrofurans and tetrahydropyrans regioselectively is described. Mechanistic studies have shown that the tetrahydrofurans can stereoselectively rearrange to the corresponding tetrahydropyrans.

  DOI：

  10.1021/ol200127n
• 作为产物：
  描述：

  (4E)-4-癸烯-1-醇 在 Oxone 作用下， 以 水 、 异丙醇 为溶剂， 反应 0.17h， 生成 (1R)-1-[(2S)-oxolan-2-yl]hexan-1-ol
  参考文献：
  名称：

  Oxidative cyclization of alkenols with Oxone using a miniflow reactor

  摘要：

  开发了一种使用Oxone进行烯醇氧化环化的小流量系统。因此，(Z)-和(E)-烯醇在-PrOH中与Oxone的水溶液在PTFE管中顺利、安全地进行氧化环化，无需任何外源催化物，并随后以流动反应方式迅速熄灭，在5或10分钟的停留时间内定量地得到相应的呋喃基和吡喃基羟基化合物。

  DOI：

  10.3762/bjoc.5.18

文献信息

• Oxidative cyclization of 5-hydroxyalkenes with rhenium oxide, utilizing a co-oxidant. IV
  作者：Suhan Tang、Robert M. Kennedy

  DOI：10.1016/s0040-4039(00)79078-2

  日期：1992.9

  5-Hydroxylalkenes react with rhenium(VII) oxide in the presence of another oxidant, H5IO6, to provide substituted tetrahydrofurans. The yield and stereoselectivity are comparable to stoichiometric results.

  5-羟基烯烃与氧化rh（VII）在另一种氧化剂H 5 IO 6的存在下反应，提供取代的四氢呋喃。产率和立体选择性与化学计量结果相当。
• Determination of absolute configuration of stereogenic carbinol centers in annonaceous acetogenins by proton and fluorine 19-NMR analysis of Mosher ester derivatives
  作者：Matthew J. Rieser、Yu Hua Hui、J. Kent Rupprecht、John F. Kozlowski、Karl V. Wood、Jerry L. McLaughlin、Paul R. Hanson、Zhiping Zhuang、Thomas R. Hoye

  DOI：10.1021/ja00052a018

  日期：1992.12

  The absolute configuration of the stereogenic carbinol centers in nine annonaceous acetogenins has been determined by careful 1 H- and 19 F-NMR analysis of (S)- and (R)-Mosher ester [methoxy(trifluoromethyl)phenylacetate or MTPA] derivatives. These acetogenins include five adjacent bis-tetrahydrofuran acetogenins [uvaricin (3), bullatacin (4), bullatacinone (5), asimicin (6), and rolliniastatin 1 (7)]

  通过对 (S)- 和 (R)-Mosher 酯 [甲氧基（三氟甲基）苯基乙酸酯或 MTPA] 衍生物进行仔细的 1 H-和 19 F-NMR 分析，确定了九个番荔枝苷元中立体生成甲醇中心的绝对构型。这些 acetogenins 包括五个相邻的双四氢呋喃 acetogenins [uvaricin (3)、bulatacin (4)、bulatacinone (5)、asimicin (6) 和 rolliniastatin 1 (7)] 和四个单四氢呋喃 acetogenins [reticulatacin (8)、isoannonacin -10-一 (9)、番红花素-10-一 (10) 和番红花素 (11)]
• Tightly Convoluted Polymeric Phosphotungstate Catalyst:  An Oxidative Cyclization of Alkenols and Alkenoic Acids
  作者：Yoichi M. A. Yamada、Haiqing Guo、Yasuhiro Uozumi

  DOI：10.1021/ol070258v

  日期：2007.4.1

  A tightly convoluted polymeric phosphotungstate catalyst was prepared via ionic assembly of H3PW12O40 and poly(alkylpyridinium). An oxidative cyclization of various alkenols and alkenoic acids was efficiently promoted by the polymeric catalyst in aq H2O2 in the absence of organic solvents to afford the corresponding cyclic ethers and lactones in high yield. The catalyst was reused four times without loss of catalytic activity.
• Directed oxidative cyclization of 5-hydroxyalkenes with rhenium oxide
  作者：Robert M. Kennedy、Suhan Tang

  DOI：10.1016/0040-4039(92)80010-h

  日期：1992.6

  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.
• Acid-Catalyzed Regioselective Sulfetherification of Alkenols and Stereoselective Rearrangement of Tetrahydrofuran to Tetrahydropyran
  作者：Haining Wang、Deshun Huang、Donghao Cheng、Lijun Li、Yian Shi

  DOI：10.1021/ol200127n

  日期：2011.4.1

  An efficient acid-catalyzed sulfetherification of various unsaturated alcohols with sulfenamides to form tetrahydrofurans and tetrahydropyrans regioselectively is described. Mechanistic studies have shown that the tetrahydrofurans can stereoselectively rearrange to the corresponding tetrahydropyrans.