(+)-1αH,7αH,10βH-guaia-4,11-dien-3-one | 871711-84-1

• 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: (+)-1αH,7αH,10βH-guaia-4,11-dien-3-one
• 英文别名: (5R,8R,8aS)-3,8-dimethyl-5-prop-1-en-2-yl-4,5,6,7,8,8a-hexahydro-1H-azulen-2-one
• CAS: 871711-84-1
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: CESATEXQMONATC-RTXFEEFZSA-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：

  (+)-1αH,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52%的产率得到(-)-1αH,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 4-二甲氨基吡啶 、 氢氧化钾 、 n-butyl tin hydride 、 偶氮二异丁腈 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 14.34h， 生成 (+)-1αH,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

• 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.