trans-1-(2-furyl)-menthan-1-ol | 173928-55-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: trans-1-(2-furyl)-menthan-1-ol
• 英文别名: (1S,2S,5R)-1-(furan-2-yl)-5-methyl-2-propan-2-ylcyclohexan-1-ol
• CAS: 173928-55-7
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: KHBFZGRBXMTADO-DYEKYZERSA-N

物化性质

• 沸点：
  313.1±17.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-1-(2-furyl)-menthan-1-ol 在 Jones'reagent 、 氯化二乙基铝 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 8.5h， 生成
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions with a chiral spirodione, (6S, 7S, 10R)-7-Isopropyl-10-methyl-1-oxaspiro[5.5]undec-3-ene-2,5-dione

  摘要：

  The synthesis of the title spirodione, a new class of auxiliary based chiral synthon, using (-)-menthone having a unique carbon-carbon bond is described. Diels-Alder reactions were carried out with variety of dienes using the title auxiliary as a chiral dienophile in the presence of diethyl aluminium chloride as Lewis acid catalyst to afford the cycloadduct with good diastereoselectivity. The configurations of the chiral synthon and cycloadducts were determined by X-ray crystallography. Methodology for detachment of the chiral auxiliary from the cycloadducts has been developed.

  DOI：

  10.1016/0957-4166(95)00393-2
• 作为产物：
  描述：

  呋喃 、 (-)-薄荷酮 在 正丁基锂 作用下， 生成 trans-1-(2-furyl)-menthan-1-ol
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions with a chiral spirodione, (6S, 7S, 10R)-7-Isopropyl-10-methyl-1-oxaspiro[5.5]undec-3-ene-2,5-dione

  摘要：

  The synthesis of the title spirodione, a new class of auxiliary based chiral synthon, using (-)-menthone having a unique carbon-carbon bond is described. Diels-Alder reactions were carried out with variety of dienes using the title auxiliary as a chiral dienophile in the presence of diethyl aluminium chloride as Lewis acid catalyst to afford the cycloadduct with good diastereoselectivity. The configurations of the chiral synthon and cycloadducts were determined by X-ray crystallography. Methodology for detachment of the chiral auxiliary from the cycloadducts has been developed.

  DOI：

  10.1016/0957-4166(95)00393-2

文献信息

• Highly Diastereoselective and Asymmetric Diels−Alder Reactions of Masked <i>o</i>-Benzoquinones with Chiral Racemic and Homochiral Furans. Synthesis of Optically Active Tricyclic γ-Lactones
  作者：Yu-Yu Chou、Rama Krishna Peddinti、Chun-Chen Liao

  DOI：10.1021/ol034278i

  日期：2003.5.1

  [reaction: see text] The first examples of highly diastereoselective and asymmetric Diels-Alder cycloadditions of in situ generated masked o-benzoquinones (MOBs) with chiral racemic and homochiral furans bearing a chiral center in the alpha-position leading to highly functionalized diastereomeric/enantioselective tricyclic heterocycles and chiral tricyclic gamma-lactones are described.

  [反应：请参阅文字]原位生成的高度非对映选择性和不对称Diels-Alder环加成反应的第一个例子是，在手性外消旋和同手性呋喃中，手性中心位于α-位，导致高度官能化的非对映异构体/描述了对映选择性三环杂环和手性三环γ-内酯。