(5S,6S,7S,2E,8E)-7-(tert-butyldimethylsilyloxy)-2,6,8-trimethyl-2,8-decadien-1,5-diol | 760985-16-8

• 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: (5S,6S,7S,2E,8E)-7-(tert-butyldimethylsilyloxy)-2,6,8-trimethyl-2,8-decadien-1,5-diol
• 英文别名: (2E,5S,6S,7S,8E)-7-[tert-butyl(dimethyl)silyl]oxy-2,6,8-trimethyldeca-2,8-diene-1,5-diol
• CAS: 760985-16-8
• 化学式: C₁₉H₃₈O₃Si
• 分子量: 342.594
• InChiKey: IWDHTVWNCZHCOR-CQGULOPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S,6S,7S,2E,8E)-7-(tert-butyldimethylsilyloxy)-2,6,8-trimethyl-2,8-decadien-1,5-diol 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 以55%的产率得到(5S,6S,7S,2E,8E)-2,6,8-trimethyl-2,8-decadien-1,5,7-triol
  参考文献：
  名称：

  Kulokekahilide-2, a Cytotoxic Depsipeptide from a Cephalaspidean Mollusk Philinopsis speciosa

  摘要：

  A cytotoxic depsipeptide, kulokekahilide-2 (1), was isolated from a cephalaspidean mollusk, Philinopsis speciosa. The structure elucidation of kulokekahilide-2 was carried out by spectroscopic analysis and chemical degradation. Kulokekahilide-2 showed potent cytotoxicity against several cell lines (P388, SKOV-3, MDA-MB-435, and A-10 with IC50 values ranging from 4.2 to 59.1 nM) indicating cancer cell selectivity.

  DOI：

  10.1021/np049949f
• 作为产物：
  描述：

  (2R,3S,4E)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-4-hexenal 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 三氟乙酸吡啶 、 二异丁基氢化铝 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 6.5h， 生成 (5S,6S,7S,2E,8E)-7-(tert-butyldimethylsilyloxy)-2,6,8-trimethyl-2,8-decadien-1,5-diol
  参考文献：
  名称：

  Kulokekahilide-2, a Cytotoxic Depsipeptide from a Cephalaspidean Mollusk Philinopsis speciosa

  摘要：

  A cytotoxic depsipeptide, kulokekahilide-2 (1), was isolated from a cephalaspidean mollusk, Philinopsis speciosa. The structure elucidation of kulokekahilide-2 was carried out by spectroscopic analysis and chemical degradation. Kulokekahilide-2 showed potent cytotoxicity against several cell lines (P388, SKOV-3, MDA-MB-435, and A-10 with IC50 values ranging from 4.2 to 59.1 nM) indicating cancer cell selectivity.

  DOI：

  10.1021/np049949f

文献信息

• Kulokekahilide-2, a Cytotoxic Depsipeptide from a Cephalaspidean Mollusk <i>Philinopsis speciosa</i>
  作者：Yoichi Nakao、Wesley Y. Yoshida、Yuuki Takada、Junji Kimura、Liu Yang、Susan L. Mooberry、Paul J. Scheuer

  DOI：10.1021/np049949f

  日期：2004.8.1

  A cytotoxic depsipeptide, kulokekahilide-2 (1), was isolated from a cephalaspidean mollusk, Philinopsis speciosa. The structure elucidation of kulokekahilide-2 was carried out by spectroscopic analysis and chemical degradation. Kulokekahilide-2 showed potent cytotoxicity against several cell lines (P388, SKOV-3, MDA-MB-435, and A-10 with IC50 values ranging from 4.2 to 59.1 nM) indicating cancer cell selectivity.