9β-Hydroxy-3-oxo-(7αH,6,11βH)-eudesm-4-en-6,12-olide | 144460-99-1

• 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: 9β-Hydroxy-3-oxo-(7αH,6,11βH)-eudesm-4-en-6,12-olide
• 英文别名: (3S,3aS,5S,5aS,9bS)-5-hydroxy-3,5a,9-trimethyl-3a,4,5,6,7,9b-hexahydro-3H-benzo[g][1]benzofuran-2,8-dione
• CAS: 144460-99-1
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: HMPXOJCJHLLTCB-GPJWAORESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9β-Hydroxy-3-oxo-(7αH,6,11βH)-eudesm-4-en-6,12-olide 在 Raney Ni W-2 六甲基磷酰三胺 、 三氟化硼乙醚 、 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， 反应 13.33h， 生成 9β-Hydroxy-(7αH,6βH)-eudesma-4,11(13)-dien-6,12-olide
  参考文献：
  名称：

  Synthesis of the reported structure of herbolide I and its C-11 epimer from artemisin

  摘要：

  Artemisin (1) was converted into 12 (the reported structure for herbolide I) and its C-11 epimer 19 via a synthetic pathway involving a functionality transfer from C-8 to C-9 and an A-ring refunctionalization. The H-1 and C-13 NMR data of synthetic products 12 and 19 reveal that the assigned structure of the natural herbolide I is erroneous.

  DOI：

  10.1021/jo00077a051
• 作为产物：
  描述：

  3-Oxo-(7αH,6,11βH)-eudesma-4,8-dien-6,12-olide 在 Raney Ni W-2 甲基环氧丙烷 、 titanium(IV) isopropylate 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 36.5h， 生成 9β-Hydroxy-3-oxo-(7αH,6,11βH)-eudesm-4-en-6,12-olide
  参考文献：
  名称：

  Synthesis of the reported structure of herbolide I and its C-11 epimer from artemisin

  摘要：

  Artemisin (1) was converted into 12 (the reported structure for herbolide I) and its C-11 epimer 19 via a synthetic pathway involving a functionality transfer from C-8 to C-9 and an A-ring refunctionalization. The H-1 and C-13 NMR data of synthetic products 12 and 19 reveal that the assigned structure of the natural herbolide I is erroneous.

  DOI：

  10.1021/jo00077a051

文献信息

• 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.
• Ultrasound assisted reductive cleavage of sesquiterpene γ-enonelactones
  作者：Victoria Bargues、Gonzalo Blay、Luz Cardona、B. Garcia、José R. Pedro

  DOI：10.1016/0040-4039(95)01742-z

  日期：1995.11

  Ultrasound enhances the rate of reductive cleavage of the C-6-oxygen bond of several cis- and trans- sesquiterpene gamma-enonelactones. Interestingly ultrasound overrides the stereoelectronic requirements for the reductive cleavage of the most usually occurring sesquiterpene trans-lactones.
• Functionality transfer from C8 to C9 in sesquiterpenes. Synthesis of the named Herbolide E from artemisin.
  作者：Gonzalo Blay、Luz Cardona、Begoña García、José R. Pedro

  DOI：10.1016/s0040-4039(00)79147-7

  日期：1992.9

  The key intermediate 6 was obtained in five steps from artemisin (1). The spectroscopic characteristics of the synthetic product 7a reveal that the proposed structure for the natural herbolide E must be revised.
• Synthesis of 9-oxyfunctionalized eudesmanes from artemisin
  作者：Victoria Bargues、Gonzalo Blay、Begoña García、Cristina L. García、JoséR. Pedro

  DOI：10.1016/0040-4020(95)00221-s

  日期：1995.5

  Artemisin (1) was transformed into two natural sesquiterpenoids 2 and 3 in a sequence which involves functionality transfer from C-8 to C-9 and further elaboration of the A ring and the lactone moiety.
• Synthesis of the reported structure of herbolide I and its C-11 epimer from artemisin
  作者：Gonzalo Blay、Luz Cardona、Begona Garcia、Jose R. Pedro

  DOI：10.1021/jo00077a051

  日期：1993.12

  Artemisin (1) was converted into 12 (the reported structure for herbolide I) and its C-11 epimer 19 via a synthetic pathway involving a functionality transfer from C-8 to C-9 and an A-ring refunctionalization. The H-1 and C-13 NMR data of synthetic products 12 and 19 reveal that the assigned structure of the natural herbolide I is erroneous.

表征谱图