(5R,6S,8S,9S,E)-6,8,10-tris(tert-butyldimethylsilyloxy)-4,5,9-trimethyl-3-decen-1-yne | 1428738-05-9

• 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: (5R,6S,8S,9S,E)-6,8,10-tris(tert-butyldimethylsilyloxy)-4,5,9-trimethyl-3-decen-1-yne
• 英文别名: [(E,2S,3S,5S,6R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2,6,7-trimethyldec-7-en-9-ynoxy]-tert-butyl-dimethylsilane
• CAS: 1428738-05-9
• 化学式: C₃₁H₆₄O₃Si₃
• 分子量: 569.104
• InChiKey: PLVQZLRZQHCPJJ-GMLBCSGKSA-N

物化性质

• 沸点：
  514.7±50.0 °C(predicted)
• 密度：
  0.881±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.03
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,6S,8S,9S,E)-6,8,10-tris(tert-butyldimethylsilyloxy)-4,5,9-trimethyl-3-decen-1-yne 在 四(三苯基膦)钯 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.5h， 生成 (1R,2S,6R,7S,9S,10S,E)-7,9,11-tris(tert-butyldimethylsilyloxy)-1-{(2R,4R,5S)-5-[2-(tertbutyldiphenylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}-1-(4-methoxybenzyloxy)-5,6,10-trimethyl-3-methyleneundec-4-en-2-ol
  参考文献：
  名称：

  Synthesis of the C-1–C-17 Fragment of Amphidinolides C, C2, C3, and F

  摘要：

  The C-1-C-17 fragment of amphidinolides C, C2, C3, and F has been constructed from a trans-2,5-disubstituted dihydrofuranone prepared by diastereoselective rearrangement of a free or metal-bound oxonium ylide generated from a metal carbenoid. The dihydrofuranone was converted into an aldehyde corresponding to the C-1-C-8 framework, and this was coupled to the C-9-C-17 unit by nucleophilic addition of a vinylic anion.

  DOI：

  10.1021/ol4004838
• 作为产物：
  描述：

  (S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester 在 2,6-二甲基吡啶 、 diisobutylaluminium hydride 、 氯代二环己基硼烷 、 异丙基氯化镁 、 sodium hexamethyldisilazane 、 potassium carbonate 、 戴斯-马丁氧化剂 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 34.0h， 生成 (5R,6S,8S,9S,E)-6,8,10-tris(tert-butyldimethylsilyloxy)-4,5,9-trimethyl-3-decen-1-yne
  参考文献：
  名称：

  Synthesis of the C-1–C-17 Fragment of Amphidinolides C, C2, C3, and F

  摘要：

  The C-1-C-17 fragment of amphidinolides C, C2, C3, and F has been constructed from a trans-2,5-disubstituted dihydrofuranone prepared by diastereoselective rearrangement of a free or metal-bound oxonium ylide generated from a metal carbenoid. The dihydrofuranone was converted into an aldehyde corresponding to the C-1-C-8 framework, and this was coupled to the C-9-C-17 unit by nucleophilic addition of a vinylic anion.

  DOI：

  10.1021/ol4004838

文献信息

• Synthesis of the C-1–C-17 Fragment of Amphidinolides C, C2, C3, and F
  作者：J. Stephen Clark、Guang Yang、Andrew P. Osnowski

  DOI：10.1021/ol4004838

  日期：2013.4.5

  The C-1-C-17 fragment of amphidinolides C, C2, C3, and F has been constructed from a trans-2,5-disubstituted dihydrofuranone prepared by diastereoselective rearrangement of a free or metal-bound oxonium ylide generated from a metal carbenoid. The dihydrofuranone was converted into an aldehyde corresponding to the C-1-C-8 framework, and this was coupled to the C-9-C-17 unit by nucleophilic addition of a vinylic anion.