(-)-1βH,7αH,10βH-guaia-4,11-dien-3-one | 7764-53-6

• 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: (-)-1βH,7αH,10βH-guaia-4,11-dien-3-one
• 英文别名: (5R,8R,8aR)-3,8-dimethyl-5-prop-1-en-2-yl-4,5,6,7,8,8a-hexahydro-1H-azulen-2-one
• CAS: 7764-53-6
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: CESATEXQMONATC-RAIGVLPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-1βH,7αH,10βH-guaia-4,11-dien-3-one 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 反应 0.15h， 以50%的产率得到(-)-1βH,7αH,10βH-guaia-4,11-diene
  参考文献：
  名称：

  Synthesis of (+)-pechueloic acid and (+)-aciphyllene. Revision of the structure of (+)-aciphyllene

  摘要：

  1 alpha H,7 alpha H,10 alpha H-Guaia-4,11-dien-3-one and its 1 beta H,10 beta H diastereomer, easily obtained from (+)-dihydrocarvone, are good starting materials for the synthesis of natural guaiane derivatives. Allylic oxidation of the 1 alpha H,10 alpha H isomer gave as main product its 13- hydroxy derivative and a small amount of (+)-7 beta-hydroxy-1 alpha H,10 alpha H-guaia-4,11-dien-3-one, whereas the 1 beta H, 10 beta H diastereomer afforded selectively the (-)-7 alpha-hydroxy-1 beta H,10 beta H enantiomer in excellent yield. From the 13-hydroxy derivative (+)-pechueloic acid and (+)-methyl pechueloate were synthesized. Deoxygenation at C-3 of the 1 beta H,10 beta H guaiadienone afforded a guaiadiene with the reported structure for aciphyllene but its spectral data did not agree with those reported for the natural diene. The structure of natural (+)-aciphyllene has been corrected to 1 alpha H,7 alpha H,10 alpha H-guaia-4,11-diene obtained by deoxygenation of the 1 alpha H,10 alpha H guaiadienone. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.039
• 作为产物：
  描述：

  (4aS,7R)-1,4a-dimethyl-7-isopropenyl-5,6,7,8-tetrahydronaphthalene-2-(4aH)-one 在 正丙胺 、 lithium 、 溶剂黄146 、 乙二胺 作用下， 反应 6.2h， 生成 (-)-1βH,7αH,10βH-guaia-4,11-dien-3-one
  参考文献：
  名称：

  所有7α的合成ħ dihydrocarvone - -guaia -4,11-二烯-3-酮非对映体从（+）

  摘要：

  所有四个7α ħ -guaia -4,11-二烯-3-酮非对映体已被从共同中间体1α合成ħ，10α -乙酰氧基- 7α ħ -guaia -4,11-二烯-3-酮从获得的（+） -二氢香芹酮。四个非对映体的光谱特征已被相关的结构和1β的绝对构ħ，10β ħ，7α ħ -guaia -4,11-二烯-3-酮从分离Pleocarphus revolutus已被证实。

  DOI：

  10.1016/j.tet.2005.09.026

文献信息

• Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction
  作者：Yuye Chen、Wenqing Chen、Zhiting Zhang、Jing Xu

  DOI：10.1002/cjoc.202400014

  日期：——

  natural products, cyclopentenones usually can be fabricated by Nazarov cyclization using divinyl ketones or functionalized tertiary divinyl carbinols (TDCs) as substrates. However, straightforward method for transforming unfunctionalized TDCs to their corresponding cyclopentenones is currently lacking. Herein, we wish to report the total syntheses of four structurally distinct terpenoids, namely laurane-type

  作为天然产物中最常见的结构基序之一，环戊烯酮通常可以使用二乙烯基酮或功能化叔二乙烯基甲醇（TDC）作为底物通过纳扎罗夫环化来制备。然而，目前缺乏将未功能化的 TDC 转化为其相应环戊烯酮的直接方法。在此，我们希望报告四种结构不同的萜类化合物的全合成，即月桂烷型海洋倍半萜类异月桂烯、去溴海兔素和海兔素，以及愈创木烷倍半萜类愈创木二烯酮A，所有这些都使用一种新颖的合成方法，称为氧化纳扎罗夫环化作为关键步骤。这项工作证明了我们稳健的方法适用于合成各种高度取代的环戊烯酮。
• Synthesis of all 7αH-guaia-4,11-dien-3-one diastereomers from (+)-dihydrocarvone
  作者：Gonzalo Blay、Begoña Garcia、Eva Molina、José R. Pedro

  DOI：10.1016/j.tet.2005.09.026

  日期：2005.11

  All four 7αH-guaia-4,11-dien-3-one diastereomers have been synthesized from the common intermediate 1αH,10α-acetoxy-7αH-guaia-4,11-dien-3-one obtained from (+)-dihydrocarvone. The spectral features of the four diasteromers have been correlated and the structure and absolute configuration of 1βH,10βH,7αH-guaia-4,11-dien-3-one isolated from Pleocarphus revolutus has been confirmed.

  所有四个7α ħ -guaia -4,11-二烯-3-酮非对映体已被从共同中间体1α合成ħ，10α -乙酰氧基- 7α ħ -guaia -4,11-二烯-3-酮从获得的（+） -二氢香芹酮。四个非对映体的光谱特征已被相关的结构和1β的绝对构ħ，10β ħ，7α ħ -guaia -4,11-二烯-3-酮从分离Pleocarphus revolutus已被证实。
• Synthesis of (+)-pechueloic acid and (+)-aciphyllene. Revision of the structure of (+)-aciphyllene
  作者：Gonzalo Blay、Begoña Garcia、Eva Molina、José R. Pedro

  DOI：10.1016/j.tet.2007.07.039

  日期：2007.9

  1 alpha H,7 alpha H,10 alpha H-Guaia-4,11-dien-3-one and its 1 beta H,10 beta H diastereomer, easily obtained from (+)-dihydrocarvone, are good starting materials for the synthesis of natural guaiane derivatives. Allylic oxidation of the 1 alpha H,10 alpha H isomer gave as main product its 13- hydroxy derivative and a small amount of (+)-7 beta-hydroxy-1 alpha H,10 alpha H-guaia-4,11-dien-3-one, whereas the 1 beta H, 10 beta H diastereomer afforded selectively the (-)-7 alpha-hydroxy-1 beta H,10 beta H enantiomer in excellent yield. From the 13-hydroxy derivative (+)-pechueloic acid and (+)-methyl pechueloate were synthesized. Deoxygenation at C-3 of the 1 beta H,10 beta H guaiadienone afforded a guaiadiene with the reported structure for aciphyllene but its spectral data did not agree with those reported for the natural diene. The structure of natural (+)-aciphyllene has been corrected to 1 alpha H,7 alpha H,10 alpha H-guaia-4,11-diene obtained by deoxygenation of the 1 alpha H,10 alpha H guaiadienone. (c) 2007 Elsevier Ltd. All rights reserved.