4-((tert-butyldimethylsilyl)oxy)phenethyl acetate | 596804-01-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-((tert-butyldimethylsilyl)oxy)phenethyl acetate
• 英文别名: 4-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}phenethyl acetate；2-[4-[Tert-butyl(dimethyl)silyl]oxyphenyl]ethyl acetate
• CAS: 596804-01-2
• 化学式: C₁₆H₂₆O₃Si
• 分子量: 294.466
• InChiKey: CEWMYFLORGXNBP-UHFFFAOYSA-N

物化性质

• 沸点：
  329.8±25.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  4-((tert-butyldimethylsilyl)oxy)phenethyl acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以96%的产率得到2-(4{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanol
  参考文献：
  名称：

  TX-2152: A conformationally rigid and electron-rich diyne analogue of FTY720 with in vivo antiangiogenic activity

  摘要：

  We designed FTY720 analogues with conformationally rigid and electron-rich acetylenic chains as anti-angiogenic agents ( the monoyne 1: TX-2148, the diyne 2: TX-2152, the triyne 3: TX-2256). Molecular orbital ( MO) calculations of our designed acetylenic analogues and FTY720 showed that the localization of the lowest unoccupied MO and the highest occupied MO increased from phenyl ring to acetylenic chain compared with that of FTY720. These acetylenic analogues were synthesized from p-hydroxyphenylethanol as a starting material. The construction of the acetylenic chain was carried out by an iterative strategy using a Sonogashira cross-coupling reaction and desilylative bromination in two steps. The corresponding overall yields of the monoyne 1, the diyne 2, and the triyne 3 were 27% ( 11 steps), 13% ( 13 steps), and 10% ( 15 steps). The in vivo antiangiogenic activities of these acetylenic analogues and FTY720 were evaluated by the chick embryo chorioallantoic membrane ( CAM) assay and compared to the activities of the known antiangiogenic agent TNP-470. The diyne 2 showed more potent antiangiogenic activity ( 90% inhibition) than FTY720 ( 77% inhibition) and other acetylenic analogues ( the monoyne 1: 42% inhibition, the triyne 3: 60% inhibition), and TNP-470 ( 82% inhibition) at a dose of 10 mu g/CAM, without showing toxicity. The diyne 2 also had potent inhibitory activity at a dose of 5 and 2.5 mu g/CAM. These results indicate that the flexibility of C8 alkyl chain of FTY720 is not required for its antiangiogenic activity. We suggest that the diyne 2 ( TX-2152) may be a promising candidate as an antiangiogenic agent for antineoplastic drug discovery. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.003
• 作为产物：
  描述：

  (tert-butyl)dimethyl(4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)phenoxy)silane 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 4-((tert-butyldimethylsilyl)oxy)phenethyl acetate
  参考文献：
  名称：

  使用 SO3H 硅胶去除非甲硅烷基保护基团的脱保护程序

  摘要：

  摘要 保护基团在有机合成中是必不可少的，对各种脱保护方法的需求很大。在这里，我们研究了使用 SO3H 硅胶的脱保护程序的应用范围，我们之前已将其报告为脱甲硅烷化程序。在这些条件下，-OMOM、-OSEM、-OTHP 和-OAc 基团和二甲基乙缩醛被裂解。新戊酰氧基、苄氧基和甲氧基羰基保持完整，并且在其他保护基团存在下实现了 TBS 基团的选择性脱保护。我们成功地裂解了高极性去甲托品衍生物中仲醇上的乙酰基。我们的发现提供了另一种脱保护选择，将有助于多功能化合物的合成。图形概要

  DOI：

  10.1080/00397911.2018.1548023

文献信息

• ZrCl4 as a mild and efficient catalyst for the one-pot conversion of TBS and THP ethers to acetates
  作者：Ch.Sanjeeva Reddy、G Smitha、S Chandrasekhar

  DOI：10.1016/s0040-4039(03)01078-5

  日期：2003.6

  A mild, efficient and chemoselective method has been developed for the direct transformation of tert-butyldimethylsilyl and tetrahydropyranyl protected alcohols into the corresponding acetates with acetic anhydride and zirconium(IV) chloride as the catalyst in acetonitrile, in a one-pot reaction with high yields and short reaction times. This method has been applied to a variety of substrates. (C) 2003 Elsevier Science Ltd. All rights reserved.