10'R-acetoxy-11'-hydroxyumbelliprenin | 1187322-67-3

• 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: 10'R-acetoxy-11'-hydroxyumbelliprenin
• 英文别名: [(3R,6E,10E)-2-hydroxy-2,6,10-trimethyl-12-(2-oxochromen-7-yl)oxydodeca-6,10-dien-3-yl] acetate
• CAS: 1187322-67-3
• 化学式: C₂₆H₃₄O₆
• 分子量: 442.552
• InChiKey: XSNVYFAOCSBLDV-PKPWYKSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  10'R-karatavicinol 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以53%的产率得到10'R-acetoxy-11'-hydroxyumbelliprenin
  参考文献：
  名称：

  A Practical Synthesis of a Hydroxylated Sesquiterpene Coumarin 10’R-Acetoxy-11’-hydroxyumbelliprenin by Regioselective Dihydroxylation

  摘要：

  A practical synthesis of 10'R-acetoxy-11'-hydroxyumbelliprenin was achieved using regioselective Sharpless asymmetric dihydroxylation as a key reaction, in which the regioselectivity was achieved by using (DHQD)(2)AQN as a ligand instead of the conventional (DHQD)(2)PHAL. 10'R-Acetoxy-11'-hydroxyumbelliprenin was synthesized by the coupling of a coumarin unit (umbelliferone) and sesquiterpene unit in 11% overall yield through 5 steps.

  DOI：

  10.3987/com-12-12636

文献信息

• COMPOSITION FOR TREATING INFLUENZA A (H1N1) VIRUS AND A PREPARATION METHOD THEREFOR
  申请人：Wu Yang-Chang

  公开号：US20110196029A1

  公开（公告）日：2011-08-11

  New pharmaceutical compositions extracted from Ferula assa - foetida are confirmed to effectively treat influenza A (H 1 N 1 ) virus. The extraction method of the new pharmaceutical compositions mainly includes steps of (a) extracting F. assa - foetida with methanol to obtain a crude extract; (b) fractioning the crude extract with n-hexane-methanol to obtain a methanol extract; (c) fractioning the methanol extract with chloroform-water to obtain a chloroform extract; and (d) chromatographing the chloroform extract to obtain the pharmaceutical compositions, which can be further fractioned and chromatographed to obtain various sesquiterpene coumarins.
• US8476311B2
  申请人：——

  公开号：US8476311B2

  公开（公告）日：2013-07-02
• US8815949B2
  申请人：——

  公开号：US8815949B2

  公开（公告）日：2014-08-26
• US8993618B2
  申请人：——

  公开号：US8993618B2

  公开（公告）日：2015-03-31
• A Practical Synthesis of a Hydroxylated Sesquiterpene Coumarin 10’R-Acetoxy-11’-hydroxyumbelliprenin by Regioselective Dihydroxylation
  作者：Kenichi Akaji、Yasunao Hattori、Genki Kinami、Kenta Teruya、Kazuto Nosaka、Kazuya Kobayashi

  DOI：10.3987/com-12-12636

  日期：——

  A practical synthesis of 10'R-acetoxy-11'-hydroxyumbelliprenin was achieved using regioselective Sharpless asymmetric dihydroxylation as a key reaction, in which the regioselectivity was achieved by using (DHQD)(2)AQN as a ligand instead of the conventional (DHQD)(2)PHAL. 10'R-Acetoxy-11'-hydroxyumbelliprenin was synthesized by the coupling of a coumarin unit (umbelliferone) and sesquiterpene unit in 11% overall yield through 5 steps.