cis-(1S,5S)-(+)-pulegol | 118760-35-3

• 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: cis-(1S,5S)-(+)-pulegol
• 英文别名: (+)-(1S,5S)-pulegol；Cyclohexanol, 5-methyl-2-(1-methylethylidene)-, (1S,5S)-；(1S,5S)-5-methyl-2-propan-2-ylidenecyclohexan-1-ol
• CAS: 118760-35-3
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: JGVWYJDASSSGEK-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• 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：

  cis-(1S,5S)-(+)-pulegol 在 氢氧化钾 、 五氯化磷 、 丙酸 作用下， 以 四氯化碳 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 p-nitrophenyl (-)-(1'S,5'S)-(2'-isopropylidene-5'-methylcyclohex-1'-yl)acetate
  参考文献：
  名称：

  Lactones 23: Synthesis of cis-fused bicyclic hydroxy lactones with a p-menthane system

  摘要：

  Enantiomeric pairs of cis-fused bicyclic hydroxy lactones with a p-menthane system were obtained in a several step synthesis from enantiornerically pure isomers of (+)-(R)- and (-)-(S)-pulegone. One-pot allyl-Claisen rearrangement of cis-pulegols, epoxidation of gamma,delta-unsaturated p-nitrophenyl esters and acidic lactonization of epoxy esters are key synthetic steps. The structures of the compounds were confirmed by both spectroscopic and crystallographic methods. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.020
• 作为产物：
  描述：

  (-)-蒲勒酮 (S)-(-)-长叶薄荷酮 (S)-2-异亚丙基-5-甲基环己酮 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 2.0h， 生成 cis-(1S,5S)-(+)-pulegol
  参考文献：
  名称：

  内酯。21.具有对-薄荷烷体系的内酯的合成和香气性质。

  摘要：

  从（R）-（+）-和（S）-（-）-普乐酮开始，得到具有对-薄荷烷体系的酯和内酯的对映体对。烯丙基醇的克莱森重排和γ，δ-不饱和酸的碘内酯化是提出的合成的关键步骤。化合物的结构通过光谱和晶体学方法确定。一些合成的化合物的特征在于令人感兴趣的气味性质。

  DOI：

  10.1021/jf035272a

文献信息

• Cyclopropanation with Dibromomethane under Grignard and Barbier Conditions
  作者：Fridtjof Schröder、Gerhard Brunner、Laura Eberhard、Jürg Oetiker

  DOI：10.1055/s-0029-1216999

  日期：2009.11

  from α-substituted (homo)allyl alcohols. In tandem reactions, cyclopropyl carbinols are obtained from allyloxylithium or -magnesium intermediates, generated in situ by alkylation of conjugated aldehydes, ketones, and esters as well as from allyl esters and carbonates or vinyloxiranes. [¹] cyclopropanation - Barbier conditions - Grignard addition - alkyllithium addition - dibromomethane

  格氏试剂和二溴甲烷在环境温度下，在乙醚溶剂中有效地环丙酸烯丙基（和某些均烯丙基）镁和锂醇化物。在较高的Barbier条件下，将（均）烯丙基锂醇盐与镁和二溴甲烷直接环丙烷化。反应速率取决于（均）烯丙基醇化物的取代方式和取决于锂的抗衡离子，其效果最佳。从α-取代的（均）烯丙基醇获得良好至优异的顺选择性。在串联反应中，环丙基甲醇是从烯丙氧基锂或镁中间体获得的，该中间体是通过共轭醛，酮和酯的烷基化以及烯丙基酯和碳酸酯或乙烯基氧杂环戊烷而原位生成的。[ ¹] 环丙烷化-Barbier条件-Grignard加成-烷基锂加成-二溴甲烷
• Synthesis of Terpenoid Lactones with thep-Menthane System
  作者：Iwona Dams、Agata Białońska、Zbigniew Ciunik、Czesław Wawrzeńczyk

  DOI：10.1002/ejoc.200300800

  日期：2004.6

  Starting from (R)-(+)- and (S)-(−)-pulegone enantiomeric pairs of hydroxy lactones and keto lactones were obtained by Claisen rearrangement of cis-pulegols and lactonization of epoxy esters. The hydroxy lactones were reduced with LiAlH4 in order to assign the configuration of the chiral centers. The structures of the synthesized compounds were established on the basis of spectroscopic and crystallographic

  从 (R)-(+)- 和 (S)-(-)-pulegone 对映体对羟基内酯和酮内酯对通过顺式-pulegols 的 Claisen 重排和环氧酯的内酯化获得。羟基内酯用 LiAlH4 还原以分配手性中心的构型。合成化合物的结构是在光谱和晶体学数据的基础上建立的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Lactones 23: Synthesis of cis-fused bicyclic hydroxy lactones with a p-menthane system
  作者：Iwona Dams、Agata Białońska、Zbigniew Ciunik、Czesław Wawrzeńczyk

  DOI：10.1016/j.tetasy.2005.04.020

  日期：2005.6

  Enantiomeric pairs of cis-fused bicyclic hydroxy lactones with a p-menthane system were obtained in a several step synthesis from enantiornerically pure isomers of (+)-(R)- and (-)-(S)-pulegone. One-pot allyl-Claisen rearrangement of cis-pulegols, epoxidation of gamma,delta-unsaturated p-nitrophenyl esters and acidic lactonization of epoxy esters are key synthetic steps. The structures of the compounds were confirmed by both spectroscopic and crystallographic methods. (c) 2005 Elsevier Ltd. All rights reserved.
• Lactones. 21. Synthesis and Odoriferous Properties of Lactones with the <i>p</i>-Menthane System
  作者：Iwona Dams、Agata Białońska、Zbigniew Ciunik、Czesław Wawrzeńczyk

  DOI：10.1021/jf035272a

  日期：2004.3.1

  Starting from (R)-(+)- and (S)-(-)-pulegone, enantiomeric pairs of esters and lactones with the p-menthane system were obtained. The Claisen rearrangement of allylic alcohols and iodolactonization of gamma,delta-unsaturated acids were the key steps of syntheses presented. The structures of compounds were determined by both spectroscopic and crystallographic methods. Some of the synthesized compounds

  从（R）-（+）-和（S）-（-）-普乐酮开始，得到具有对-薄荷烷体系的酯和内酯的对映体对。烯丙基醇的克莱森重排和γ，δ-不饱和酸的碘内酯化是提出的合成的关键步骤。化合物的结构通过光谱和晶体学方法确定。一些合成的化合物的特征在于令人感兴趣的气味性质。