1α,7α,10αH-guaia-4,11-dien-3-one | 120838-14-4

• 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: 1α,7α,10αH-guaia-4,11-dien-3-one
• 英文别名: (+)-1αH,7αH,10αH-guaia-4,11-dien-3-one；1alpha,7alpha,10alphaH-Guaia-4,11-dien-3-one；(5R,8S,8aS)-3,8-dimethyl-5-prop-1-en-2-yl-4,5,6,7,8,8a-hexahydro-1H-azulen-2-one
• CAS: 120838-14-4
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: CESATEXQMONATC-UHTWSYAYSA-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：

  1α,7α,10αH-guaia-4,11-dien-3-one 在 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 以28%的产率得到(+)-13-hydroxy-1αH,7αH,10αH-guaia-4,11-dien-3-one
  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：

  (5R,8S,8aS)-5-((S)-2-Hydroxy-1-methyl-ethyl)-3,8-dimethyl-1,2,4,5,6,7,8,8a-octahydro-azulen-2-ol 在 manganese(IV) oxide 、 三丁基膦 、 双氧水 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 29.5h， 生成 1α,7α,10αH-guaia-4,11-dien-3-one
  参考文献：
  名称：

  Ultrasound assisted reductive cleavage of eudesmane and guaiane γ-enonelactones. Synthesis of 1α,7α,10αH-guaian-4,11-dien-3-one and hydrocolorenone from santonin

  摘要：

  Ultrasound enhances the rate of reductive cleavage of the C-6-oxygen bond of sesquiterpene enonelactones. trans-Eudesmanolides 1c-1g, cis-eudesmanolides 2a-2c, and trans-guaianolides 4a-4d react with Zn in acetic acid-H2O under sonochemical conditions to afford the corresponding sesquiterpene. acids 3a-3g and 5a-5d, respectively in good yields. Starting from 5d two natural guaianes 1 alpha ,7 alpha ,10 alphaH-guaian-4, 11-dien-3-one (6) and hydrocolorenone (7) have been prepared in good yields through a straightforward sequence. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00986-3

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。
• A Bioinspired Approach to Tri-<i>nor</i>-guaianes. Synthesis of (−)-Clavukerin A
  作者：Gonzalo Blay、Begoña García、Eva Molina、José R. Pedro

  DOI：10.1021/np060184g

  日期：2006.8.1

  degradation of the C-7 side chain of related guaia-11-enes is described. In this approach (-)-clavukerin A (1) is obtained by selective ozonolysis-Criegge rearrangement of (+)-1alphaH,7alphaH,10alphaH-guaia-4,11-dien-3-one (4) to afford 7beta-hydroxy and 7beta-acetoxy tri-nor-guaiane derivatives 6 and 7, respectively, which after elimination and deoxygenation give the title compound. The starting guaiadienone

  描述了通过降解相关的guaia-11-enes C-7侧链的生物启发的方法来制备tri-nor-guaianes。在这种方法中，通过选择性的臭氧分解-（+）-1alphaH，7alphaH，10alphaH-guaia-4,11-dien-3-one（4）的臭氧重排-Criegge重排获得（-）-clavukerin A（1），得到7beta-hydroxy和7β-乙酰氧基三正瓜氨酸衍生物6和7，它们在消除和脱氧后得到标题化合物。起始愈创木酚二酮易于从市售的桑顿宁或（+）-二氢香芹酮中获得。
• Ultrasound assisted reductive cleavage of eudesmane and guaiane γ-enonelactones. Synthesis of 1α,7α,10αH-guaian-4,11-dien-3-one and hydrocolorenone from santonin
  作者：Gonzalo Blay、Victoria Bargues、Luz Cardona、Begoña Garcı́a、José R Pedro

  DOI：10.1016/s0040-4020(01)00986-3

  日期：2001.11

  Ultrasound enhances the rate of reductive cleavage of the C-6-oxygen bond of sesquiterpene enonelactones. trans-Eudesmanolides 1c-1g, cis-eudesmanolides 2a-2c, and trans-guaianolides 4a-4d react with Zn in acetic acid-H2O under sonochemical conditions to afford the corresponding sesquiterpene. acids 3a-3g and 5a-5d, respectively in good yields. Starting from 5d two natural guaianes 1 alpha ,7 alpha ,10 alphaH-guaian-4, 11-dien-3-one (6) and hydrocolorenone (7) have been prepared in good yields through a straightforward sequence. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.