5-methyl-5-vinyltetrahydrofuran-2-ol | 40478-73-7

• 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: 5-methyl-5-vinyltetrahydrofuran-2-ol
• 英文别名: 5-ethenyl-5-methyloxolan-2-ol
• CAS: 40478-73-7
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: BIJAVMAZHUQEJX-UHFFFAOYSA-N

物化性质

• 沸点：
  175.9±40.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  5-methyl-5-vinyltetrahydrofuran-2-ol 在 sodium hydroxide 、 lutidine 、 苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 50.0h， 生成 (E)-6-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,7-dienoic acid
  参考文献：
  名称：

  Synthesis of (±)-(E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid and the corresponding amide (“acacialactam”)

  摘要：

  The total synthesis of the title compounds in racemic form is described. Linalool was used as the starting material and transformed into the target molecules in 6 steps. The synthetic amide displays spectral properties identical to those reported for the natural compound acacialactam, indicating that the structure proposed for the latter compound is not correct.

  DOI：

  10.1016/s0040-4039(00)76907-3
• 作为产物：
  描述：

  芳樟醇 在 盐酸 、 4-二甲氨基吡啶 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 5-methyl-5-vinyltetrahydrofuran-2-ol
  参考文献：
  名称：

  Arteperoxides A–C，三-降单萜-倍半萜与来自 Artemisia judaica 的过氧化物桥结合，表现出抗破骨细胞活性

  摘要：

  对埃及收集的 120 种药用植物提取物进行了抗破骨细胞引导筛选，最终选择了Artemisia judaica L.（菊科）。三种未描述的与达瓦酮相关的萜类化合物，蒿过氧化物 A–C，与两种已知的衍生物羟基达瓦酮和达瓦那酸一起从提取物中分离出来。结构分析显示青蒿过氧化物 A–C 是具有过氧化物桥的三-降单萜-倍半萜偶联物。尽管已从蒿中分离出具有过氧化物（如氢过氧基和过氧半缩酮基团）的达瓦酮衍生物物种中，蒿过氧化物 A-C 是第一个观察到的在两个萜烯衍生单元之间含有过氧化物桥的变体。arteperoxides A 和 B 的绝对构型是根据它们的光谱数据与具有醚键的半合成类似物进行比较研究的。测试了天然和合成化合物的抗破骨细胞活性，青蒿过氧化物 C 和羟基达瓦酮在 20 μM 时比其他化合物更有效。

  DOI：

  10.1016/j.phytochem.2022.113548

文献信息

• On the use of anomeric hydroxylamines in the reverse-Cope cyclisation
  作者：Nigel P. Bainbridge、Angela C. Currie、Nicholas J. Cooper、James C. Muir、David W. Knight、Jonathan M. Walton

  DOI：10.1016/j.tetlet.2007.09.027

  日期：2007.10

  Reverse-Cope cyclisations of unsaturated hydroxylamines, when the latter are anomeric, are shown to be a viable approach to a variety of hexahydrofuro[2,3-b]pyrrole 6-oxides. (C) 2007 Elsevier Ltd. All rights reserved.
• Gas-Phase Reactions of Nopinone, 3-Isopropenyl-6-oxo-heptanal, and 5-Methyl-5-vinyltetrahydrofuran-2-ol with OH, NO₃, and Ozone
  作者：Aggelos Calogirou、Niels R. Jensen、Claus J. Nielsen、Dimitrios Kotzias、Jens Hjorth

  DOI：10.1021/es980530j

  日期：1999.2.1

  In the troposphere, alpha-pinene, beta-pinene, limonene, and linalool are mainly oxidized to pinonaldehyde, nopinone, 3-isopropenyl-6-oxoheptanal (IPOH), and 5-methyl-5-vinyltetrahydrofuran-2-ol ( MVT), respectively. The rate constant of the reactions of nopinone, IPOH, and MVT with OH, NO3, and O-3 were determined by long path FT-IR spectroscopy, and the oxidation products from the reactions between the OH radical and pinonaldehyde, nopinone, IPOH, and MVT were investigated using GC-MS and HPLC. The reaction rate constants (k) for the reactions have been determined at 740 +/- 5 Torr and 298 +/- 5 K, and a number of reaction products were identified. The rate constants obtained for the reactions with nopinone were k(OH) = (1.7 +/- 0.2) x 10(-11), k(NO3) < 2 x 10(-15) and k(O3) < 5 x 10(-21); far the reactions with IPOH were k(OH) = (1.1 +/- 0.3) x 10(-10), k(NO3) = (2.6 +/- 0.8) x 10(-13), and k(O3) = (8.3 +/- 2.2) x 10(-18); and for the reactions with MVT were k(OH) = (7.4 +/- 0.9) x 10(-11), k(NO3) = (2.0 +/- 0.9) x 10(-14) and k(O3) = (3.8 +/- 0.8) x 10(-18) (all units are in cm(3) molecule(-1) s(-1), and uncertainties are given as two sigma on the experimental data). From the results obtained in this investigation and previous studies, it was concluded that a typical atmospheric lifetime with respect to chemical reactions was only a few hours for pinonaldehyde, IPOH, and MVT but was much longer for nopinone with a lifetime of about 10 h.
• JPH05202017A
  申请人：——

  公开号：JPH05202017A

  公开（公告）日：1993-08-10
• Synthesis of (±)-(E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid and the corresponding amide (“acacialactam”)
  作者：Miguel Carda、Juan Murga、J.Alberto Marco

  DOI：10.1016/s0040-4039(00)76907-3

  日期：1994.5

  The total synthesis of the title compounds in racemic form is described. Linalool was used as the starting material and transformed into the target molecules in 6 steps. The synthetic amide displays spectral properties identical to those reported for the natural compound acacialactam, indicating that the structure proposed for the latter compound is not correct.
• Arteperoxides A–C, tris-normonoterpene–sesquiterpene conjugates with peroxide-bridges from Artemisia judaica exhibiting antiosteoclastogenic activity
  作者：Ahmed H. El-Desoky、Toshifumi Asano、Yuka Maeyama、Hikaru Kato、Yuki Hitora、Eishu Goto、Shunsuke Kotani、Makoto Nakajima、Sachiko Tsukamoto

  DOI：10.1016/j.phytochem.2022.113548

  日期：2023.2

  known derivatives, hydroxydavanone and davana acid. Structural analysis revealed that arteperoxides A–C were tris-normonoterpene–sesquiterpene conjugates with peroxide bridges. Although davanone derivatives with peroxides, such as a hydroperoxyl and peroxyhemiketal groups, have been isolated from Artemisia species, arteperoxides A–C are the first variations observed to contain peroxide bridges between

  对埃及收集的 120 种药用植物提取物进行了抗破骨细胞引导筛选，最终选择了Artemisia judaica L.（菊科）。三种未描述的与达瓦酮相关的萜类化合物，蒿过氧化物 A–C，与两种已知的衍生物羟基达瓦酮和达瓦那酸一起从提取物中分离出来。结构分析显示青蒿过氧化物 A–C 是具有过氧化物桥的三-降单萜-倍半萜偶联物。尽管已从蒿中分离出具有过氧化物（如氢过氧基和过氧半缩酮基团）的达瓦酮衍生物物种中，蒿过氧化物 A-C 是第一个观察到的在两个萜烯衍生单元之间含有过氧化物桥的变体。arteperoxides A 和 B 的绝对构型是根据它们的光谱数据与具有醚键的半合成类似物进行比较研究的。测试了天然和合成化合物的抗破骨细胞活性，青蒿过氧化物 C 和羟基达瓦酮在 20 μM 时比其他化合物更有效。