Formic acid (1R,2R,5R,6S,9R,12S)-2-acetyl-5,9-dimethyl-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-12-yl ester | 127867-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: Formic acid (1R,2R,5R,6S,9R,12S)-2-acetyl-5,9-dimethyl-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-12-yl ester
• 英文别名: [(1R,2R,5R,6S,9R,12S)-2-acetyl-5,9-dimethyl-10,11,13-trioxatricyclo[7.2.2.01,6]tridecan-12-yl] formate
• CAS: 127867-60-1
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: ZPLAEYFSCSICSG-UDYJRIAMSA-N

物化性质

• 熔点：
  103-104 °C(Solvent: Hexane; Diethyl ether)
• 沸点：
  386.5±42.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Formic acid (1R,2R,5R,6S,9R,12S)-2-acetyl-5,9-dimethyl-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-12-yl ester 在 ruthenium trichloride 、 sodium periodate 、 4 A molecular sieve 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 2-((3R,5aS,6R,8aS,9S,11R,11aR)-3,6,9-trimethyloctahydro-3H,11H-3,11-epoxy[1,2]dioxepino[3,4-d]isobenzofuran-9-yl)acetaldehyde
  参考文献：
  名称：

  Synthesis and Cytotoxicity Studies of Artemisinin Derivatives Containing Lipophilic Alkyl Carbon Chains

  摘要：

  Cytotoxic artermisinin derivatives have been synthesized by a modular approach of '' artemisinin + linker + lipophilic alkyl carbon chain ''. A strong correlation between the length of the carbon chains and the cytotoxicities against human hepatocellular carcinoma (HepG2) was revealed. Notably, compared with artemisinin (IC50 = 97 mu M), up to 200-fold more potent cytotoxicity (IC50 = 0.46 mu M) could be achieved by attachment of a C14H29 carbon chain to artemisinin via an amide linker.

  DOI：

  10.1021/ol050230o
• 作为产物：
  描述：

  dihydroartemisinin 在 磷酸 、 亚甲兰 、 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 、 丙酮 、 苯 为溶剂， 反应 25.0h， 生成 Formic acid (1R,2R,5R,6S,9R,12S)-2-acetyl-5,9-dimethyl-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-12-yl ester
  参考文献：
  名称：

  Synthesis of 6,7-dehydroartemisinic acid

  摘要：

  从黄花蒿中提取的天然产物 6,7-脱氢青蒿酸是通过四个步骤从青蒿烯合成的，而青蒿烯又是通过四个步骤从市售青蒿素制备的。正向合成涉及青蒿烯的酸降解，并对这一反应的产物与其 11,13-二氢类似物青蒿素的酸降解反应进行了一些比较。

  DOI：

  10.1039/b104471k

文献信息

• Deoxyartemisinin Derivatives from Photooxygenation of Anhydrodeoxydihydroartemisinin and Their Cytotoxic Evaluation
  作者：Ahmed M. Galal、Samir A. Ross、Mahmoud A. ElSohly、Hala N. ElSohly、Farouk S. El-Feraly、Mohamed S. Ahmed、Andrew T. McPhail

  DOI：10.1021/np0104065

  日期：2002.2.1

  Photooxygenation of anhydrodeoxydihydroartemisinin (4) followed by chromatographic separation of the reaction mixture yielded the new compounds alpha- (5) and beta-hydroperoxydeoxyartemisitene (8) and the formate ester 7, together with two previously reported compounds, 6 and 9. Reduction of 5 using polymer-bound triphenylphosphine afforded the new compound dihydrodeoxyartemisitene (10). Treatment of 10 with a catalytic amount of BF3-OEt2 yielded the C-2-symmetrical dimer bis(dihydrodeoxyartemisitene) ether (11) and two new compounds, dihydrodeoxyartemisitene methyl ether (12) and the dimer 13, as minor products. Dehydroacetoxylation of 5 using acetic anhydride in pyridine afforded deoxyartemisitene (14). The identities of the new compounds (5, 7, 8, 10-14) were deduced from their spectral data and by chemical derivatization. The stereochemistry of dimer 11 was defined on the basis of X-ray crystallographic analysis. All compounds were evaluated in vitro in the National Cancer Institute drug-screening program consisting of 60 human cancer, cell lines derived from nine different tissues. Of the compounds tested, deoxyartemisitene (14) demonstrated significant cytotoxicity against a number of human cancer cell lines.
• EL-FERALY, FAROUK S.;AYALP, ABIDIN;AL-YAHYA, MOHAMMED A.;MCPHAIL, DONALD +, J. NATUR. PROD., 53,(1990) N, C. 66-71
  作者：EL-FERALY, FAROUK S.、AYALP, ABIDIN、AL-YAHYA, MOHAMMED A.、MCPHAIL, DONALD +

  DOI：——

  日期：——