1,2,3,4,5,6,7,8-octahydro-azulen-1-ol | 875842-98-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3,4,5,6,7,8-octahydro-azulen-1-ol
• 英文别名: 1,2,3,4,5,6,7,8-Octahydroazulen-1-ol
• CAS: 875842-98-1
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: BCBLWMJOFLSWCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2,3,4,5,6,7,8-octahydro-azulen-1-ol 在 aluminum oxide 、 potassium hydrogensulfate 、 palladium/alumina 作用下， 320.0 ℃ 、2.67 kPa 条件下， 生成 奥苷菊环
  参考文献：
  名称：

  456.多环系统。第五部分：通往天青石的新途径

  摘要：

  DOI：

  10.1039/jr9530002208
• 作为产物：
  描述：

  3,4,5,6,7,8-六氢薁-1(2H)-酮 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 1,2,3,4,5,6,7,8-octahydro-azulen-1-ol
  参考文献：
  名称：

  Acid-Promoted Rearrangement of Cyclic α,β-Epoxy Acylates:  Stereoselective Synthesis of Spirocyclanes and Quaternary Carbon Centers

  摘要：

  The rearrangement reaction of alpha,beta-epoxy acylates in cyclic systems was studied. The treatment of cis-derivatives with a Lewis acid afforded rearranged products via the regioselective B-cleavage of the oxirane ring due to the electron-withdrawing nature of the acyloxy group, whereas trans-derivatives enhanced the neighboring group participation to yield only a small amount of rearranged products. This rearrangement reaction proved to be useful for the construction of st variety of spirocyclane systems or quaternary carbon centers on rings and could be applied to their syntheses as optically active forms.

  DOI：

  10.1021/jo970035q

文献信息

• [EN] 1-HYDROXY-OCTAHYDROAZULENES AS FRAGRANCES<br/>[FR] 1-HYDROXY-OCTAHYDROAZULÈNES EN TANT QUE PARFUMS
  申请人：GIVAUDAN SA

  公开号：WO2012001018A1

  公开（公告）日：2012-01-05

  (3S,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-octahydroazulen-1-ols, their use as flavour or fragrance ingredient, and a process of their production by oxidation in the presence of laccase.

  (3S,5R)-3,8-二甲基-5-(丙烯基)-八氢萘-1-醇及其作为香料或香精成分的用途，以及在漆酶存在下通过氧化反应制备它们的方法。
• Asymmetric synthesis of chiral spirocyclanes: Selective formation of 2-acyloxy-1-oxospiro[4.n]alkanes by regio- and stereoselective rearrangement of α,β-epoxy acylates in bicyclo[n.3.0]alkane systems
  作者：Hiromichi Fujioka、Shinji Kitagaki、Reiko Imai、Michinori Kondo、Sachi Okamoto、Yutaka Yoshida、Shuji Akai、Yasuyuki Kita

  DOI：10.1016/0040-4039(95)00517-g

  日期：1995.5

  Selective formation of 2-acyloxy-1-oxospiro[4.n]alkanes by regio- and stereoselective rearrangement of α,β-epoxy acylates in bicyclo[n.3.0]alkane systems has been achieved; the effect of the acyloxy group and stereochemistry of the starting epoxides were studied. The reaction was successfully applied to the synthesis of an optically active chiral spiro compound.

  通过在双环[n.3.0]烷烃体系中α，β-环氧酰化物的区域和立体选择性重排，实现了2-酰氧基-1-氧螺环[4.n]烷烃的选择性形成；研究了酰氧基的影响和起始环氧化物的立体化学。该反应成功地用于光学活性手性螺化合物的合成。
• Dev, Journal of the Indian Chemical Society, 1955, vol. 32, p. 325,330
  作者：Dev

  DOI：——

  日期：——
• 1-HYDROXY-OCTAHYDROAZULENES AS FRAGRANCES
  申请人：Givaudan SA

  公开号：EP2588436A1

  公开（公告）日：2013-05-08
• Acid-Promoted Rearrangement of Cyclic α,β-Epoxy Acylates:  Stereoselective Synthesis of Spirocyclanes and Quaternary Carbon Centers
  作者：Yasuyuki Kita、Shinji Kitagaki、Yutaka Yoshida、Sachiko Mihara、Dai-Fei Fang、Michinori Kondo、Sachi Okamoto、Reiko Imai、Shuji Akai、Hiromichi Fujioka

  DOI：10.1021/jo970035q

  日期：1997.7.1

  The rearrangement reaction of alpha,beta-epoxy acylates in cyclic systems was studied. The treatment of cis-derivatives with a Lewis acid afforded rearranged products via the regioselective B-cleavage of the oxirane ring due to the electron-withdrawing nature of the acyloxy group, whereas trans-derivatives enhanced the neighboring group participation to yield only a small amount of rearranged products. This rearrangement reaction proved to be useful for the construction of st variety of spirocyclane systems or quaternary carbon centers on rings and could be applied to their syntheses as optically active forms.