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)acetic acid | 851380-76-2

• 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: 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)acetic acid
• CAS: 851380-76-2
• 化学式: C₁₆H₂₄O₆
• 分子量: 312.363
• InChiKey: IMNRUKVDIFCUHG-XBJFJYQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  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)acetic acid 、 十二烷基伯胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到N-dodecyl-2-[(1R,4S,5R,8S,9S,11R,12R)-1,5,9-trimethyl-10,13,14,15-tetraoxatetracyclo[9.3.1.04,12.08,12]pentadecan-9-yl]acetamide
  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：

  脱水二氢青蒿素 在 ruthenium trichloride 、 Oxone 、 sodium periodate 、 4 A molecular sieve 、 碳酸氢钠 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.5h， 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)acetic acid
  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