(2R,3R)-2-((1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)hepta-6-en-3-ol | 508234-43-3

• 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: (2R,3R)-2-((1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)hepta-6-en-3-ol
• 英文别名: (2R,3R)-2-[(1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]hept-6-en-3-ol
• CAS: 508234-43-3
• 化学式: C₁₉H₃₂O
• 分子量: 276.462
• InChiKey: ZIYZPEAQQJMYBP-VLUPQCQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-((1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)hepta-6-en-3-ol 在 9-borabicyclo[3.3.1]nonane dimer 、 氧气 、 rose bengal 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 18.5h， 生成 (1R,4S,5R,8S,9R,10R,12R,13R)-10-(4-bromobutyl)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
  参考文献：
  名称：

  Antitumor Activity of Novel Deoxoartemisinin Monomers, Dimers, and Trimer

  摘要：

  The first primary amines 9 and bromoalkyl analogues 7 of deoxoartemisinin with nonacetal functionality at C-12 are prepared as versatile intermediates for the synthesis of various derivatives. Eight C-12 nonacetal type dimers and one trimer of deoxoartemisinin were prepared using novel chemistry. Dimers, particularly 12a, 18a,b, and trimer 17, were especially potent and selective at inhibiting the growth of certain human cancer cell lines and were comparable to that of clinically used anticancer drugs. The linker with one amide- or one sulfur-centered two ethylene groups of the dimers is essential for high anticancer activity. Trimer 17 shows very potent activity against most of the human cancer cell lines tested.

  DOI：

  10.1021/jm020119d
• 作为产物：
  描述：

  3-Butenylmagnesium bromide 、 dihydroartemisinic aldehyde 以 四氢呋喃 为溶剂， 以53%的产率得到(2R,3R)-2-((1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)hepta-6-en-3-ol
  参考文献：
  名称：

  二氢青蒿醛由暗单线态氧合成青蒿素类似物

  摘要：

  使用暗单线态氧从修饰的二氢青蒿酸/醛合成了一系列的青蒿素（青蒿素）类似物，从而触发了三恶烷形成的关键步骤。新近获得的1,2,4-三恶烷具有一个侧链，该侧链从对应于青蒿素内酯羰基的碳延伸到一个稳定的碳-碳单键，而不是文献中大多数类似物中的乙缩醛-碳键。生物素和各种胺也分别通过这种线性束缚与青蒿素核心相连，以努力开发杂交体和潜在有用的探针以寻找体内靶标。

  DOI：

  10.1002/cjoc.201700055

文献信息

• Synthesis of Qinghaosu Analogues from Dihydroqinghao Aldehyde: A Dark Singlet Oxygen Approach
  作者：Xunshen Liu、Huijun Chen、Zejun Xu、Yikang Wu、Bo Liu

  DOI：10.1002/cjoc.201700055

  日期：2017.4

  A range of qinghaosu (artemisinin) analogues were synthesized from modified dihydroqinghao acid/aldehyde using dark singlet oxygen to trigger off the key step of the trioxane formation. The newly accessed 1,2,4‐trioxanes featured a side chain extended from the carbon corresponding to the lactone carbonyl group of qinghaosu through a stable carbon‐carbon single bond instead of an acetal oxygen‐carbon

  使用暗单线态氧从修饰的二氢青蒿酸/醛合成了一系列的青蒿素（青蒿素）类似物，从而触发了三恶烷形成的关键步骤。新近获得的1,2,4-三恶烷具有一个侧链，该侧链从对应于青蒿素内酯羰基的碳延伸到一个稳定的碳-碳单键，而不是文献中大多数类似物中的乙缩醛-碳键。生物素和各种胺也分别通过这种线性束缚与青蒿素核心相连，以努力开发杂交体和潜在有用的探针以寻找体内靶标。
• Antitumor Activity of Novel Deoxoartemisinin Monomers, Dimers, and Trimer
  作者：Mankil Jung、Sangmin Lee、Jungyeob Ham、Kyunghoon Lee、Hanjo Kim、Soo Kie Kim

  DOI：10.1021/jm020119d

  日期：2003.3.1

  The first primary amines 9 and bromoalkyl analogues 7 of deoxoartemisinin with nonacetal functionality at C-12 are prepared as versatile intermediates for the synthesis of various derivatives. Eight C-12 nonacetal type dimers and one trimer of deoxoartemisinin were prepared using novel chemistry. Dimers, particularly 12a, 18a,b, and trimer 17, were especially potent and selective at inhibiting the growth of certain human cancer cell lines and were comparable to that of clinically used anticancer drugs. The linker with one amide- or one sulfur-centered two ethylene groups of the dimers is essential for high anticancer activity. Trimer 17 shows very potent activity against most of the human cancer cell lines tested.