13S,16S-19,25-epoxy-17(25),18-dien-16-acetoxyhyrtiosan-12-al | 138355-08-5

• 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: 13S,16S-19,25-epoxy-17(25),18-dien-16-acetoxyhyrtiosan-12-al
• 英文别名: (-)-Hyrtiosal acetate；(16S)-hyrtiosal acetate；[(1S)-2-[(2S,3S,3aR,5aS,9aS,9bR)-2-formyl-2,3a,6,6,9a-pentamethyl-3,4,5,5a,7,8,9,9b-octahydro-1H-cyclopenta[a]naphthalen-3-yl]-1-(furan-3-yl)ethyl] acetate
• CAS: 138355-08-5
• 化学式: C₂₇H₄₀O₄
• 分子量: 428.612
• InChiKey: ICLMNNHOIMGCQA-OSUFMNBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  13S,16S-19,25-epoxy-17(25),18-dien-16-acetoxyhyrtiosan-12-al 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.5h， 以96%的产率得到16S-acetoxy-19,25-epoxy-hyrtiosa-17(25)-18-dien-12-oic acid
  参考文献：
  名称：

  Biomimetic Synthesis of Two Salmahyrtisanes: Salmahyrtisol A and Hippospongide A

  摘要：

  Sesterterpenes with a salmahyrtisane skeleton have been synthesized for the first time. (-)-Sclareol has been selected as a precursor for the synthesis of two novel natural products: salmahyrtisol A (1) and hippospongide A (2). Our results represent a biomimetic approach to obtaining salmahyrtisanes from hyrtiosanes. Salmahyrtisol A has shown an activity comparable to that of the standard anticancer drugs in the cell lines A549, HBL-100, HeLa, and SW1573.

  DOI：

  10.1021/acs.joc.5b00420
• 作为产物：
  描述：

  methyl 13S-11(12->13)-abeo-12-ethylenedithiaisoanticopal-15-oate 在 吡啶 、 chromium(VI) oxide 、 正丁基锂 、 mercury(II) perchlorate 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 对甲苯磺酸 、 calcium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 3.2h， 生成 13S,16S-19,25-epoxy-17(25),18-dien-16-acetoxyhyrtiosan-12-al
  参考文献：
  名称：

  Basabe; Diego; Diez, Synlett, 2000, # 12, p. 1807 - 1809

  摘要：

  DOI：

文献信息

• Hyrtiosanes from Labdanes: (-)-Hyrtiosal from Sclareol
  作者：Pilar Basabe、Alberto Diego、David Díez、Isidro S. Marcos、Faustino Mollinedo、Julio G. Urones

  DOI：10.1055/s-2002-33332

  日期：——

  (-)-Hyrtiosal and its C-16 epimer have been prepared from sclareol in moderate yield. The absolute configuration of na­tural product (-)-hyrtiosal has being determined.

  (-)-海特酒醇及其C-16表异构体已从香根草醇中以中等产率制备。天然产物(-)-海特酒醇的绝对构型已被确定。
• Hyrtiosal, a new sesterterpenoid with a novel carbon skeleton from the Okinawan marine sponge Hyrtios erectus
  作者：Kazuo Iguchi、Yoshie Shimada、Yasuji Yamada

  DOI：10.1021/jo00028a023

  日期：1992.1

  Hyrtiosal, a new sesterterpenoid possessing a novel rearranged tricarbocyclic skeleton, was isolated from the Okinawan marine sponge, Hyrtios erectus (Keller, 1891). This compound was shown to inhibit the proliferation of KB cells in vitro, and its structure was determined by chemical and spectral methods including two-dimensional C-13-H-1 long-range correlations. The relative stereochemistry was determined based on two-dimensional NOE correlations. A possible biosynthesis of hyrtiosal is briefly discussed.