(5R,7R,8R,10S)-elema-1,3,11(13)-trien-8,12-olide | 69855-24-9

• 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: (5R,7R,8R,10S)-elema-1,3,11(13)-trien-8,12-olide
• 英文别名: 5,7,8αH-elema-1,3,11(13)-trien-8,12-olide；8α-H-Secoeudesmanolide；Eleman-8β,12-olide；8α-eudesmanolide；(3aR,5S,6S,7aR)-6-ethenyl-6-methyl-3-methylidene-5-prop-1-en-2-yl-4,5,7,7a-tetrahydro-3aH-1-benzofuran-2-one
• CAS: 69855-24-9
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: IFASGTOWHLMHEZ-QVHKTLOISA-N

物化性质

• 沸点：
  346.2±42.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5R,7R,8R,10S)-elema-1,3,11(13)-trien-8,12-olide 生成 15-hydroxy-eleman-8β,12-olide
  参考文献：
  名称：

  FRIEDRICH, DIRK;BOHLMANN, FERDINAND, TETRAHEDRON, 44,(1988) N 5, 1369-1392

  摘要：

  DOI：
• 作为产物：
  描述：

  beta-pinene 在 吡啶 、 甲醇 、 六甲基磷酰三胺 、 copper(l) iodide 、 copper(I) bromide dimethylsulfide complex 、 甲烷磺酸 、 lithium tri(t-butoxy)aluminum hydride 、 三氟化硼乙醚 、 zinc diacetate 、 氨 、 甲基锂 、 双氧水 、 乙酸酐 、 lithium 、 对甲苯磺酸 、 臭氧 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 170.67h， 生成 (5R,7R,8R,10S)-elema-1,3,11(13)-trien-8,12-olide
  参考文献：
  名称：

  The use of 4,4-disubstituted nopinones for natural-product synthesis. Synthesis of elemanoid sesquiterpenes

  摘要：

  A general and convenient synthetic route to 4,4-disubstituted nopinones 14 from (+)-nopinone (1) is developed and applied to the asymmetric synthesis of some representative elemanoid sesquiterpenes. Phenylsulfenylation of 1 provided sulfide 6 in high yield. A convenient transformation of 6 to 3-(phenylsulfonyl)-4,4-disubstituted-nopinones 13 was accomplished by (i) m-CPBA oxidation of a sulfide compound followed by the Pummerer rearrangement and (ii) the conjugate addition of carbon nucleophiles to the resulting enones, 6 --> 8 --> 9 and 9 --> 10,11 --> 13. Subsequent reductive desulfurization of the adducts 13 provided 14 in good overall yield from 1. Bicyclic ketones 14 are envisioned as promising intermediates for natural product synthesis. As examples, syntheses of two elemanoid sesquiterpenes, beta-elemenone (16) and eleman-8-beta,12-olide (17) in optically active form from (1R,4S,5S)-4,6,6-trimethyl-4-vinylbicyclo[3.1.1]heptan-2-one (14a) were carried out.

  DOI：

  10.1021/jo00025a023

文献信息

• Total synthesis of various elemanolides
  作者：Dirk Friedrich、Ferdinand Bohlmann

  DOI：10.1016/s0040-4020(01)85916-0

  日期：1988.1

  oxygen functionalities is principally possible by modification of the basic concept. Methods for the oxidative generation of terpenoid exo-methylene lactone and furan units are exemplified by synthesis of menthofuran and the -menthenolides from isopulegols.

  从合适的取代的二乙烯基环己酮开始，已经以外消旋形式合成了十一种在C-11上带有外亚甲基或甲基并且取代和相对构型不同的天然存在的12.8-电子缩水甘油醚。通过修饰基本概念，原则上可以实现具有附加的氧官能度的香豆酚的方法。氧化萜烯类exo-亚甲基内酯和呋喃单元的方法的实例是由异戊二烯合成薄荷脑甾烷醇和-薄荷醇。
• Synthesis of various natural 8,12-elemanolides from artemisin
  作者：Gonzalo Blay、Isabel Fernández、Begoña García、José R. Pedro

  DOI：10.1016/s0040-4020(01)89119-5

  日期：1989.1
• The use of 4,4-disubstituted nopinones for natural-product synthesis. Synthesis of elemanoid sesquiterpenes
  作者：Michiharu Kato、Masataka Watanabe、Bernhard Vogler、Bahlul Z. Awen、Yoshiaki Masuda、Youichi Tooyama、Akira Yoshikoshi

  DOI：10.1021/jo00025a023

  日期：1991.12

  A general and convenient synthetic route to 4,4-disubstituted nopinones 14 from (+)-nopinone (1) is developed and applied to the asymmetric synthesis of some representative elemanoid sesquiterpenes. Phenylsulfenylation of 1 provided sulfide 6 in high yield. A convenient transformation of 6 to 3-(phenylsulfonyl)-4,4-disubstituted-nopinones 13 was accomplished by (i) m-CPBA oxidation of a sulfide compound followed by the Pummerer rearrangement and (ii) the conjugate addition of carbon nucleophiles to the resulting enones, 6 --> 8 --> 9 and 9 --> 10,11 --> 13. Subsequent reductive desulfurization of the adducts 13 provided 14 in good overall yield from 1. Bicyclic ketones 14 are envisioned as promising intermediates for natural product synthesis. As examples, syntheses of two elemanoid sesquiterpenes, beta-elemenone (16) and eleman-8-beta,12-olide (17) in optically active form from (1R,4S,5S)-4,6,6-trimethyl-4-vinylbicyclo[3.1.1]heptan-2-one (14a) were carried out.
• FRIEDRICH, DIRK;BOHLMANN, FERDINAND, TETRAHEDRON, 44,(1988) N 5, 1369-1392
  作者：FRIEDRICH, DIRK、BOHLMANN, FERDINAND

  DOI：——

  日期：——