Triethylsilanyloxy-acetic acid (1R,2S)-2-phenyl-cyclohexyl ester | 195196-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Triethylsilanyloxy-acetic acid (1R,2S)-2-phenyl-cyclohexyl ester
• 英文别名: [(1R,2S)-2-phenylcyclohexyl] 2-triethylsilyloxyacetate
• CAS: 195196-20-4
• 化学式: C₂₀H₃₂O₃Si
• 分子量: 348.558
• InChiKey: CIOBNTAKVDFHTB-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-亚苄基-4-甲氧基苯胺 、 Triethylsilanyloxy-acetic acid (1R,2S)-2-phenyl-cyclohexyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(3S,4R)-1-(4-methoxyphenyl)-4-phenyl-3-tri(propan-2-yl)silyloxyazetidin-2-one
  参考文献：
  名称：

  Structure–activity relationship study of taxoids for their ability to activate murine macrophages as well as inhibit the growth of macrophage-like cells

  摘要：

  A series of new taxoids modified at the C-3', C-3'N, C-10, C-2 and C-7 positions has been designed, synthesized and evaluated for their potency to induce NO and TNF production by peritoneal murine macrophages (Mphi) from LPS-responsive C3H/HeN and LPS-hyporesponsive C3H/HeJ strains and human blood cells, and for their ability to inhibit the growth of Mphi-like cell lines J774.1 and J7.DEF3. The SAR-study has shown that the nature of the substituents at these positions have critical effect on the induction of TNF and NO production by Mphi. Positions G-3' and C-10 are the most flexible and an intriguing effect of the length of the substituents at the C-10 position is observed for taxoids bearing a straight chain alkanoyl moiety. An aromatic group at the C-3'N and C-2 positions is required for the activity, while only hydroxyl or acetyl substituents seem to be tolerated at the C-7 position. The natural stereochemistry in the C-13 isoserine side chain of the taxoids is an absolute requirement for macrophage activation. It has also been clearly shown that there is no correlation between the ability of the taxoids to induce TNF/NO production in C3H/HeN M and the cytotoxicity against Mphi-like cells. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00181-0
• 作为产物：
  描述：

  三乙基氯硅烷 、 (-)-(1R,2S)-2-phenyl-1-cyclohexyl hydroxyacetate 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以100%的产率得到Triethylsilanyloxy-acetic acid (1R,2S)-2-phenyl-cyclohexyl ester
  参考文献：
  名称：

  Totally Stereocontrolled Nitrone−Ketene Acetal Based Synthesis of (2S,3S)-N-Benzoyl- and N-Boc-phenylisoserine

  摘要：

  A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N-benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.

  DOI：

  10.1021/jo971009v