7-(tert-butyldiphenylsilyloxy)-1,1-dimethoxyhept-4-yn-3-one | 1009301-11-4

• 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: 7-(tert-butyldiphenylsilyloxy)-1,1-dimethoxyhept-4-yn-3-one
• 英文别名: 7-[Tert-butyl(diphenyl)silyl]oxy-1,1-dimethoxyhept-4-yn-3-one
• CAS: 1009301-11-4
• 化学式: C₂₅H₃₂O₄Si
• 分子量: 424.612
• InChiKey: NPLPVBXXBMUCLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(tert-butyldiphenylsilyloxy)-1,1-dimethoxyhept-4-yn-3-one 在 (1R,2R)-1,2-diphenylethylenediamine-based ruthenium complex 作用下， 以 异丙醇 为溶剂， 反应 96.0h， 以58%的产率得到(3R)-7-[tert-butyl(diphenyl)silyl]oxy-1,1-dimethoxyhept-4-yn-3-ol
  参考文献：
  名称：

  Improved Total Synthesis of the Potent HDAC Inhibitor FK228 (FR-901228)

  摘要：

  A scaleable synthesis of the potent histone deacetylase (HDAC) inhibitor FK228 is described. A reliable strategy for preparing the key,beta-hydroxy mercapto heptenoic acid partner was accomplished in nine steps and 13% overall yield. A Noyori asymmetric hydrogen-transfer reaction established the hydroxyl stereochemistry in >99:1 er via the reduction of a propargylic ketone.

  DOI：

  10.1021/ol702957z
• 作为产物：
  描述：

  N,3,3-trimethoxy-N-methylpropanamide 、 (3-丁炔-1-基氧基)(2-甲基-2-丙基)二苯基硅烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 14.5h， 以75%的产率得到7-(tert-butyldiphenylsilyloxy)-1,1-dimethoxyhept-4-yn-3-one
  参考文献：
  名称：

  Improved Total Synthesis of the Potent HDAC Inhibitor FK228 (FR-901228)

  摘要：

  A scaleable synthesis of the potent histone deacetylase (HDAC) inhibitor FK228 is described. A reliable strategy for preparing the key,beta-hydroxy mercapto heptenoic acid partner was accomplished in nine steps and 13% overall yield. A Noyori asymmetric hydrogen-transfer reaction established the hydroxyl stereochemistry in >99:1 er via the reduction of a propargylic ketone.

  DOI：

  10.1021/ol702957z

文献信息

• Org. Lett. 2008, 10, 613-616
  作者：

  DOI：——

  日期：——
• Improved Total Synthesis of the Potent HDAC Inhibitor FK228 (FR-901228)
  作者：Thomas J. Greshock、Deidre M. Johns、Yasuo Noguchi、Robert M. Williams

  DOI：10.1021/ol702957z

  日期：2008.2.1

  A scaleable synthesis of the potent histone deacetylase (HDAC) inhibitor FK228 is described. A reliable strategy for preparing the key,beta-hydroxy mercapto heptenoic acid partner was accomplished in nine steps and 13% overall yield. A Noyori asymmetric hydrogen-transfer reaction established the hydroxyl stereochemistry in >99:1 er via the reduction of a propargylic ketone.