(-)-1βH,7αH,10αH-guaia-4,11-dien-3-one | 63512-84-5

• 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,10αH-guaia-4,11-dien-3-one
• 英文别名: (5R,8S,8aR)-3,8-dimethyl-5-(prop-1-en-2-yl)-4,5,6,7,8,8a-hexahydroazulen-2(1H)-one；(-)-guaia-4,6-dien-3-one；(5R,8S,8aR)-3,8-dimethyl-5-prop-1-en-2-yl-4,5,6,7,8,8a-hexahydro-1H-azulen-2-one
• CAS: 63512-84-5
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: CESATEXQMONATC-CYZMBNFOSA-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,10αH-guaia-4,11-dien-3-one 在 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 以 癸烷 、 二氯甲烷 为溶剂， 反应 8.0h， 以28%的产率得到(5S,8S,8aR)-5-hydroxy-3,8-dimethyl-5-(prop-1-en-2-yl)-4,5,6,7,8,8a-hexahydroazulen-2(1H)-one
  参考文献：
  名称：

  Synthesis of Guaia-4(5)-en-11-ol, Guaia-5(6)-en-11-ol, Aciphyllene, 1-epi-Melicodenones C and E, and Other Guaiane-Type Sesquiterpenoids via the Diastereoselective Epoxidation of Guaiol

  摘要：

  The diastereomeric ratio of epoxidation of the internally bridged carbon-carbon double bond of guaiol (1a) is strongly influenced by the combined effects of the types of remote protecting groups on the hydroxyisopropyl side chain, choice of solvent, and epoxidizing reagent. This observation has allowed us to devise concise stereoselective syntheses of a range of guaiane-type sesquiterpenoids via an epoxidation, ring-opening/elimination, and functionality manipulation sequence. Natural products guaia-4(5)-en-11-ol (2a), guaia-5(6)-en-11-ol (3), and aciphyllene (4a) and epimers of the recently isolated natural products, 1-epi-guaia-4(5)-en-11-ol (2b), 1-epi-aciphyllene (4b), and 1-epi-melicodenones C (5a) and E (6a), were synthesized in good yields in relatively few steps.

  DOI：

  10.1021/np500611z
• 作为产物：
  描述：

  1α,7α,10αH-guaia-4,11-dien-3-one 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以19%的产率得到(-)-1βH,7αH,10αH-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

• New sesquiterpenes from Pleocarphus revolutus
  作者：Mario Silva、Alejandro Wiesenfeld、Peter G. Sammes、Thomas W. Tyler

  DOI：10.1016/0031-9422(77)80069-1

  日期：1977.1

  Abstract Six new sesquiterpenes of the guaiane and isopatchoulenone types have been isolated from the Chilean plant Pleocarphus revolutus . Of these, the compound hydroxy-isopatchoulenone and related esters showed cytotoxicity towards TLX5 mouse mammary lymphoma cells.

  摘要 从智利植物Pleocarphus revolutus 中分离到了6 个新的愈创木酚和异广藿烯酮类倍半萜。其中，复合羟基异番木香酮和相关酯类对 TLX5 小鼠乳腺淋巴瘤细胞显示出细胞毒性。
• 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 Guaia-4(5)-en-11-ol, Guaia-5(6)-en-11-ol, Aciphyllene, 1-<i>epi</i>-Melicodenones C and E, and Other Guaiane-Type Sesquiterpenoids via the Diastereoselective Epoxidation of Guaiol
  作者：An-Cheng Huang、Christopher J. Sumby、Edward R. T. Tiekink、Dennis K. Taylor

  DOI：10.1021/np500611z

  日期：2014.11.26

  The diastereomeric ratio of epoxidation of the internally bridged carbon-carbon double bond of guaiol (1a) is strongly influenced by the combined effects of the types of remote protecting groups on the hydroxyisopropyl side chain, choice of solvent, and epoxidizing reagent. This observation has allowed us to devise concise stereoselective syntheses of a range of guaiane-type sesquiterpenoids via an epoxidation, ring-opening/elimination, and functionality manipulation sequence. Natural products guaia-4(5)-en-11-ol (2a), guaia-5(6)-en-11-ol (3), and aciphyllene (4a) and epimers of the recently isolated natural products, 1-epi-guaia-4(5)-en-11-ol (2b), 1-epi-aciphyllene (4b), and 1-epi-melicodenones C (5a) and E (6a), were synthesized in good yields in relatively few steps.