(R)-N-((3R,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide | 1351186-24-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-N-((3R,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide
• 英文别名: (2R)-N-[(3R,5S)-6-[tert-butyl(diphenyl)silyl]oxy-3,5-dimethylhexyl]-2-methylbutanamide
• CAS: 1351186-24-7
• 化学式: C₂₉H₄₅NO₂Si
• 分子量: 467.767
• InChiKey: HOUCGBGXUJXYOV-CCDWMCETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-N-((3R,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide 在 正丁基锂 、 草酰氯 、 溴化亚铜二甲硫醚 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 二甲基亚砜 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.58h， 生成 (R)-N,2-dimethyl-N-((3R,5S)-3,5,6-trimethyl-8-oxo-8-((R)-2-oxo-4-phenyloxazolidin-3-yl)octyl)butanamide
  参考文献：
  名称：

  Synthesis and Biological Activity of Kalkitoxin and its Analogues

  摘要：

  Total syntheses of kalkitoxin, isolated from the Caribbean Lyngbya majuscula, and its analogues, 3-epi-, 7-epi-, 8-epi-, 10-epi-, 10-nor-, and 16-nor-kalldtcocin, were achieved via oxazolidinone-based diastereoselective 1,4-addition reaction of a methyl group and efficient T1C14-mediated thiazoline ring formation as the key steps. The biological activities of synthetic kalkitoxin and its analogues were evaluated with brine shrimp.

  DOI：

  10.1021/jo201951s
• 作为产物：
  描述：

  (R)-2-甲基丁酸 、 在 氰基磷酸二乙酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以87%的产率得到(R)-N-((3R,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide
  参考文献：
  名称：

  Synthesis and Biological Activity of Kalkitoxin and its Analogues

  摘要：

  Total syntheses of kalkitoxin, isolated from the Caribbean Lyngbya majuscula, and its analogues, 3-epi-, 7-epi-, 8-epi-, 10-epi-, 10-nor-, and 16-nor-kalldtcocin, were achieved via oxazolidinone-based diastereoselective 1,4-addition reaction of a methyl group and efficient T1C14-mediated thiazoline ring formation as the key steps. The biological activities of synthetic kalkitoxin and its analogues were evaluated with brine shrimp.

  DOI：

  10.1021/jo201951s

文献信息

• Synthesis and Biological Activity of Kalkitoxin and its Analogues
  作者：Taiki Umezawa、Manabu Sueda、Takao Kamura、Teppei Kawahara、Xuerong Han、Tatsufumi Okino、Fuyuhiko Matsuda

  DOI：10.1021/jo201951s

  日期：2012.1.6

  Total syntheses of kalkitoxin, isolated from the Caribbean Lyngbya majuscula, and its analogues, 3-epi-, 7-epi-, 8-epi-, 10-epi-, 10-nor-, and 16-nor-kalldtcocin, were achieved via oxazolidinone-based diastereoselective 1,4-addition reaction of a methyl group and efficient T1C14-mediated thiazoline ring formation as the key steps. The biological activities of synthetic kalkitoxin and its analogues were evaluated with brine shrimp.