1-Iodo-5-azidopentane | 142523-71-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-Iodo-5-azidopentane
• 英文别名: 5-azidopentyl iodide；1-azido-5-iodopentane；5-azido-1-iodopentane
• CAS: 142523-71-5
• 化学式: C₅H₁₀IN₃
• 分子量: 239.059
• InChiKey: DBDTTWIVANTBPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Iodo-5-azidopentane 在 氢气 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.5h， 生成 N-{5-[N'-(p-methylphenyl)selenoureido]pentyl}-1-deoxynojirimycin
  参考文献：
  名称：

  Selenoureido-iminosugars: A new family of multitarget drugs

  摘要：

  Herein we report the synthesis of N-alkylated deoxynojirimycin derivatives decorated with a selenoureido motif at the hydrocarbon tether as an example of unprecedented multitarget agents. Title compounds were designed as dual drugs for taclding simultaneously the Gaucher disease (by selective inhibition of beta-glucosidase, K-i = 1.6-5.5 mu M, with improved potency and selectivity compared to deoxynojirimycin) and its neurological complications (by inhibiting AChE, K-i up to 5.8 mu M). Moreover, an excellent mimicry of the selenoenzyme glutathione peroxidase was also found for the catalytic scavenging of H2O2 (K-cat/K-uncat up to 640) using PhSH as a cofactor, with improved activity compared to known positive controls, like (PhSe)(2) and ebselen; therefore, such compounds are also excellent scavengers of peroxides, an example of reactive oxygen species present at high concentrations in patients of Gaucher disease and neurological disorders. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.07.021
• 作为产物：
  描述：

  5-叠氮戊醇,5-AZIDO-1-PENTANOL 在 咪唑 、 碘 、 三苯基膦 作用下， 以93%的产率得到1-Iodo-5-azidopentane
  参考文献：
  名称：

  Selenoureido-iminosugars: A new family of multitarget drugs

  摘要：

  Herein we report the synthesis of N-alkylated deoxynojirimycin derivatives decorated with a selenoureido motif at the hydrocarbon tether as an example of unprecedented multitarget agents. Title compounds were designed as dual drugs for taclding simultaneously the Gaucher disease (by selective inhibition of beta-glucosidase, K-i = 1.6-5.5 mu M, with improved potency and selectivity compared to deoxynojirimycin) and its neurological complications (by inhibiting AChE, K-i up to 5.8 mu M). Moreover, an excellent mimicry of the selenoenzyme glutathione peroxidase was also found for the catalytic scavenging of H2O2 (K-cat/K-uncat up to 640) using PhSH as a cofactor, with improved activity compared to known positive controls, like (PhSe)(2) and ebselen; therefore, such compounds are also excellent scavengers of peroxides, an example of reactive oxygen species present at high concentrations in patients of Gaucher disease and neurological disorders. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.07.021

文献信息

• Stereoselective Synthesis of Chiral β-Fluoro α-Amino Acids via Pd(II)-Catalyzed Fluorination of Unactivated Methylene C(sp³)–H Bonds: Scope and Mechanistic Studies
  作者：Qi Zhang、Xue-Song Yin、Kai Chen、Shuo-Qing Zhang、Bing-Feng Shi

  DOI：10.1021/jacs.5b03989

  日期：2015.7.1

  direct C(sp(3))-H fluorination is attractive yet remains challenging. Here we describe the Pd(II)-catalyzed fluorination of unactivated methylene C(sp(3))-H bonds by an inner-sphere mechanism. This method allows the site- and diastereoselective fluorination of β-methylene C(sp(3))-H bonds of α-amino acid derivatives. A range of substrates containing both aliphatic and benzylic C(sp(3))-H bonds were compatible

  通过直接 C(sp(3))-H 氟化合成氟化复杂分子是有吸引力的，但仍然具有挑战性。在这里，我们通过内球机制描述了 Pd(II) 催化的未活化亚甲基 C(sp(3))-H 键的氟化。这种方法允许 α-氨基酸衍生物的 β-亚甲基 C(sp(3))-H 键的位点和非对映选择性氟化。包含脂肪族和苄基 C(sp(3))-H 键的一系列底物与该协议兼容，导致一系列 β-氟化 α-氨基酸。分离的钯环中间体的化学计量氟化在非常温和的反应条件下（室温，5-10 分钟）快速发生。初步机理研究的数据与高价中间体的直接 CF 还原消除一致。
• The Synthesis of Functionalized Cyclodextrins As Scaffolds and Templates for Molecular Diversity, Catalysis, and Inclusion Phenomena
  作者：Stephen Hanessian、Aziza Benalil、Craig Laferriere

  DOI：10.1021/jo00120a023

  日期：1995.7

  alpha-, beta- and gamma-cyclodextrins were chemically modified to selectively introduce functionality on the primary and secondary faces. Azido and substituted alkenyl groups were selectively introduced on the primary hydroxy groups to give monosubstituted derivatives. The secondary C-2 hydroxy group was selectively functionalized with allyl, 1-hexenyl, carboxymethyl, and omega-azidoalkyl groups (n: 3, 4, 5) as ethers. The chemically modified cyclodextrins are versatile molecules for use as scaffolds and templates in conjunction with chemical diversity, catalysis, and inclusion phenomena.
• 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.