(S)-7-(trimethylsilyl)hept-1-en-6-yn-4-ol | 209345-84-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-7-(trimethylsilyl)hept-1-en-6-yn-4-ol
• 英文别名: (4S)-7-trimethylsilylhept-1-en-6-yn-4-ol
• CAS: 209345-84-6
• 化学式: C₁₀H₁₈OSi
• 分子量: 182.338
• InChiKey: PWDBMIJSPHFHQI-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-7-(trimethylsilyl)hept-1-en-6-yn-4-ol 在 咪唑 、 potassium fluoride 、 Me₃SnCu*LiBr 、 Swern oxidn 、 甲基锂 、 potassium hydride 、 potassium carbonate 、 对甲苯磺酸 、 臭氧 、 lithium,azanidylidenemethylidenecopper,2H-thiophen-2-ide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 magnesium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (3S,7S)-7-Benzyloxy-5-oxo-8-((S)-4-oxo-oxetan-2-yl)-3-triisopropylsilanyloxy-octanal
  参考文献：
  名称：

  Stereocontrolled synthesis of the CD subunit of the marine macrolide altohyrtin A

  摘要：

  A synthesis of the C17-C28 segment of altohyrtin A is reported. The synthesis uses a coupling step between two chiral subunits, both of which were synthesized from L-malic acid. The remaining stereocenters were obtained through a combination of stereoselective reactions and thermodynamic equilibration. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00686-8
• 作为产物：
  描述：

  2H-吡喃,四氢-2-[(2S)-噁丙环基甲氧基]- 在 copper(l) iodide 、 sodium hydride 、 对甲苯磺酸 、 1-(2,4,6-三异丙基苯基磺酰)咪唑 作用下， 生成 (S)-7-(trimethylsilyl)hept-1-en-6-yn-4-ol
  参考文献：
  名称：

  Stereocontrolled synthesis of the CD subunit of the marine macrolide altohyrtin A

  摘要：

  A synthesis of the C17-C28 segment of altohyrtin A is reported. The synthesis uses a coupling step between two chiral subunits, both of which were synthesized from L-malic acid. The remaining stereocenters were obtained through a combination of stereoselective reactions and thermodynamic equilibration. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00686-8

文献信息

• Total Synthesis of RNA-Polymerase Inhibitor Ripostatin B and 15-Deoxyripostatin A
  作者：Wufeng Tang、Evgeny V. Prusov

  DOI：10.1002/anie.201108749

  日期：2012.4.2

  me skipped: A highly convergent total synthesis of ripostatin B, an inhibitor of the bacterial RNA polymerase, is described. The key steps to construct and avoid isomerization of the skipped triene are a double Stille cross‐coupling reaction and a ring‐closing metathesis. Furthermore, 15‐deoxyripostatin A, a stable and conformationally locked analogue of ripostatin A (see scheme, 15‐OH group red),

  让我跳过：描述了一种高度聚合的ripostatin B（细菌RNA聚合酶的抑制剂）的总合成。构造和避免跳过的三烯异构化的关键步骤是双重Stille交叉偶联反应和闭环易位。此外，还制备了15-脱氧ripostatin A（一种稳定且构象锁定的ripostatin A类似物（参见方案，15-OH组红色），并在体内进行了测试。
• Stereocontrolled synthesis of the CD subunit of the marine macrolide altohyrtin A
  作者：Ronald Zemribo、Keith T. Mead

  DOI：10.1016/s0040-4039(98)00686-8

  日期：1998.6

  A synthesis of the C17-C28 segment of altohyrtin A is reported. The synthesis uses a coupling step between two chiral subunits, both of which were synthesized from L-malic acid. The remaining stereocenters were obtained through a combination of stereoselective reactions and thermodynamic equilibration. (C) 1998 Elsevier Science Ltd. All rights reserved.