O-(tert-butyldimethylsilyl)-5-fluorotryptophol | 101349-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: O-(tert-butyldimethylsilyl)-5-fluorotryptophol
• 英文别名: tert-butyl-[2-(5-fluoro-1H-indol-3-yl)ethoxy]-dimethylsilane
• CAS: 101349-34-2
• 化学式: C₁₆H₂₄FNOSi
• 分子量: 293.457
• InChiKey: DSADPEAUIOGOCP-UHFFFAOYSA-N

物化性质

• 沸点：
  368.6±32.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-(tert-butyldimethylsilyl)-5-fluorotryptophol 在 4-二甲氨基吡啶 咪唑 、 四丁基氟化铵 、 水 、 碘 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.33h， 生成 2-O-(5-aminopentyl)-1-O-[2-[1-(t-butoxycarbonyl)-5-fluoroindol-3-yl]ethyl]-4,5-dichlorocatechol
  参考文献：
  名称：

  Catechol:  A Minimal Scaffold for Non-Peptide Peptidomimetics of the i + 1 and i + 2 Positions of the β-Turn of Somatostatin

  摘要：

  The design, synthesis, and evaluation of a series of catechol-based non-peptide peptidomimetics of the peptide hormone somatostatin have been achieved. These ligands comprise the simplest known non-peptide mimetics of the i+1 and i+2 positions of the somatostatin, ss-turn. Incorporation of an additional side chain to include the i position of the, ss-turn induces a selective 9-fold affinity enhancement at the sst(2) receptor.

  DOI：

  10.1021/ol061488x
• 作为产物：
  描述：

  5-氟吲哚-3-乙酸 在 咪唑 、 lithium aluminium tetrahydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 O-(tert-butyldimethylsilyl)-5-fluorotryptophol
  参考文献：
  名称：

  Catechol:  A Minimal Scaffold for Non-Peptide Peptidomimetics of the i + 1 and i + 2 Positions of the β-Turn of Somatostatin

  摘要：

  The design, synthesis, and evaluation of a series of catechol-based non-peptide peptidomimetics of the peptide hormone somatostatin have been achieved. These ligands comprise the simplest known non-peptide mimetics of the i+1 and i+2 positions of the somatostatin, ss-turn. Incorporation of an additional side chain to include the i position of the, ss-turn induces a selective 9-fold affinity enhancement at the sst(2) receptor.

  DOI：

  10.1021/ol061488x

文献信息

• .alpha.-Nitroarylation of ketones and esters: an exceptionally facile synthesis of indoles, 2-indolinones and arylacetic acids
  作者：T. V. RajanBabu、Bertrand L. Chenard、Michael A. Petti

  DOI：10.1021/jo00360a014

  日期：1986.5
• Highly Asymmetric Bromocyclization of Tryptophol: Unexpected Accelerating Effect of DABCO-Derived Bromine Complex
  作者：Huan Liu、Guangde Jiang、Xixian Pan、Xiaolong Wan、Yisheng Lai、Dawei Ma、Weiqing Xie

  DOI：10.1021/ol5004109

  日期：2014.4.4

  Highly asymmetric bromocyclization of tryptophol by using chiral anionic phase-transfer catalyst and DABCO-derived brominating reagent is described. Optimization of the reaction conditions revealed that the reaction rate was accelerated together with improvement of enantioselectivity by addition of catalytic DABCO-derived brominating reagent. From tryptophol, 3-bromofuroindoline could be directly obtained in excellent enantioselectivities by employing this novel methodology.
• RAJANBABU, T. V.;CHENARD, B. L.;PETTI, M. A., J. ORG. CHEM., 1986, 51, N 10, 1704-1712
  作者：RAJANBABU, T. V.、CHENARD, B. L.、PETTI, M. A.

  DOI：——

  日期：——
• Catechol:  A Minimal Scaffold for Non-Peptide Peptidomimetics of the <i>i</i> + 1 and <i>i </i>+ 2 Positions of the β-Turn of Somatostatin
  作者：Brendan P. Mowery、Vidya Prasad、Craig S. Kenesky、Angie R. Angeles、Laurie L. Taylor、Jin-Jye Feng、Wen-Long Chen、Atsui Lin、Fong-Chi Cheng、Amos B. Smith、Ralph Hirschmann

  DOI：10.1021/ol061488x

  日期：2006.9.1

  The design, synthesis, and evaluation of a series of catechol-based non-peptide peptidomimetics of the peptide hormone somatostatin have been achieved. These ligands comprise the simplest known non-peptide mimetics of the i+1 and i+2 positions of the somatostatin, ss-turn. Incorporation of an additional side chain to include the i position of the, ss-turn induces a selective 9-fold affinity enhancement at the sst(2) receptor.