1-(t-butoxycarbonyl)-3-(2-hydroxyethyl)-5-fluoroindole | 913941-83-0

• 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: 1-(t-butoxycarbonyl)-3-(2-hydroxyethyl)-5-fluoroindole
• 英文别名: tert-butyl 5-fluoro-3-(2-hydroxyethyl)-1H-indole-1-carboxylate；Tert-butyl 5-fluoro-3-(2-hydroxyethyl)indole-1-carboxylate；tert-butyl 5-fluoro-3-(2-hydroxyethyl)indole-1-carboxylate
• CAS: 913941-83-0
• 化学式: C₁₅H₁₈FNO₃
• 分子量: 279.311
• InChiKey: SFBCSTGGNHKTTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(t-butoxycarbonyl)-3-(2-hydroxyethyl)-5-fluoroindole 在 咪唑 、 水 、 碘 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 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 4-二甲氨基吡啶 咪唑 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(t-butoxycarbonyl)-3-(2-hydroxyethyl)-5-fluoroindole
  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

• Enantioselective Halocyclization of Indole Derivatives: Using 1,3-Dihalohydantoins with Anionic Chiral Co(III) Complexes
  作者：Ting-Ting Sun、Kun Liu、Shun-Xin Zhang、Jie Yu、Chun-Ru Wang、Chuan-Zhi Yao

  DOI：10.1055/a-1310-5213

  日期：2021.4

  Highly enantioselective halocyclization reactions of indole derivatives, including tryptophols and tryptamines, have been accomplished by means of anionic chiral Co(III) complexes and 1,3-dihalohydantoins (as little as 0.50 equiv). 3-Halo-fused indolines were obtained in excellent yields (up to 98%) and enantioselectivities (up to 98% ee), employing the chiral anion phase-transfer-catalysis strategy.

  摘要：利用阴离子手性Co（III）配合物和1,3-二卤代海因杜因（仅需0.50当量）实现了吲哚衍生物的高度对映选择性卤环化反应，包括色氨酸醇和色氨酸胺。采用手性阴离子相转移催化策略，得到了3-卤代融合吲哚烷，收率高（高达98％）和对映选择性高（高达98％ee）。
• 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.
• 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.