(1R)-1-[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxytridecyl]oxolan-2-yl]trideca-2,12-diyn-1-ol | 1021346-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (1R)-1-[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxytridecyl]oxolan-2-yl]trideca-2,12-diyn-1-ol
• CAS: 1021346-09-7
• 化学式: C₃₆H₆₆O₃Si
• 分子量: 575.004
• InChiKey: ZHPCSGOLDADVLX-BAQBVXSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.35
• 重原子数：
  40
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxytridecyl]oxolan-2-yl]trideca-2,12-diyn-1-ol 、 2-溴嘧啶 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以98%的产率得到(R)-1-((2R,5R)-5-((R)-1-((tert-butyldimethylsilyl)oxy)tridecyl)tetrahydrofuran-2-yl)-13-(pyrimidin-2-yl)trideca-2,12-diyn-1-ol
  参考文献：
  名称：

  Synthesis of hybrid acetogenins, α,β-unsaturated-γ-lactone-free nitrogen-containing heterocyclic analogues, and their cytotoxicity against human cancer cell lines

  摘要：

  A series of alpha,beta-unsaturated-gamma-lactone-free nitrogen-containing heterocyclic analogues of solamin, a natural mono-THF acetogenin, have been synthesized and their cytotoxicity was investigated against 39 tumor cell lines. One of them, 1-methylpyrazol-5-yl derivative, showed selective increase of cytotoxicity against NCI-H23 with 80 times higher potency than solamin. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.057
• 作为产物：
  描述：

  1,11-十二二炔 、 (2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxytridecyl]oxolane-2-carbaldehyde 在 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 三乙胺 作用下， 以 甲苯 为溶剂， 以87%的产率得到(1R)-1-[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxytridecyl]oxolan-2-yl]trideca-2,12-diyn-1-ol
  参考文献：
  名称：

  Synthesis of hybrid acetogenins, α,β-unsaturated-γ-lactone-free nitrogen-containing heterocyclic analogues, and their cytotoxicity against human cancer cell lines

  摘要：

  A series of alpha,beta-unsaturated-gamma-lactone-free nitrogen-containing heterocyclic analogues of solamin, a natural mono-THF acetogenin, have been synthesized and their cytotoxicity was investigated against 39 tumor cell lines. One of them, 1-methylpyrazol-5-yl derivative, showed selective increase of cytotoxicity against NCI-H23 with 80 times higher potency than solamin. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.057

文献信息

• Synthesis of hybrid acetogenins, α,β-unsaturated-γ-lactone-free nitrogen-containing heterocyclic analogues, and their cytotoxicity against human cancer cell lines
  作者：Naoto Kojima、Tetsuya Fushimi、Naoyoshi Maezaki、Tetsuaki Tanaka、Takao Yamori

  DOI：10.1016/j.bmcl.2008.01.057

  日期：2008.3

  A series of alpha,beta-unsaturated-gamma-lactone-free nitrogen-containing heterocyclic analogues of solamin, a natural mono-THF acetogenin, have been synthesized and their cytotoxicity was investigated against 39 tumor cell lines. One of them, 1-methylpyrazol-5-yl derivative, showed selective increase of cytotoxicity against NCI-H23 with 80 times higher potency than solamin. (c) 2008 Elsevier Ltd. All rights reserved.