4-azido-N-benzyloxycarbonyl-1-butylamine | 123348-73-2

• 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: 4-azido-N-benzyloxycarbonyl-1-butylamine
• 英文别名: benzyl (4-azidobutyl)carbamate；Benzyl N-(4-azidobutyl)carbamate
• CAS: 123348-73-2
• 化学式: C₁₂H₁₆N₄O₂
• 分子量: 248.285
• InChiKey: FHJAOSHMNVRZEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-azido-N-benzyloxycarbonyl-1-butylamine 在 sodium tetrahydroborate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 6.0h， 生成 benzyl N-(<8-(benzyloxycarbonyl)amino>-4-azaoctyl)carbamate
  参考文献：
  名称：

  Convenient routes to alkyl-substituted polyamines

  摘要：

  DOI：

  10.1016/s0040-4039(00)82421-1
• 作为产物：
  描述：

  4-(Z-氨基)-1-丁醇 在 sodium azide 、 四丁基溴化铵 、 三乙胺 作用下， 以 水 、 甲苯 为溶剂， 反应 26.0h， 生成 4-azido-N-benzyloxycarbonyl-1-butylamine
  参考文献：
  名称：

  属于B型酰基多胺结构的蜘蛛毒素NPTX-594的构效关系研究

  摘要：

  为了阐明被称为 NPTX-594 的蜘蛛毒素的构效关系，设计并合成了 11 种毒素类似物，以及它们对蟋蟀的麻痹活性...

  DOI：

  10.1246/bcsj.77.331

文献信息

• Remote Radical Azidation of Unactivated C(sp³)–H Bonds in Sulfamoyl Azides
  作者：Jiawei Li、Sishi Zhong、Pan Zhou、Xu Li、Danyang Xie、Yunfei Cai、Yong Xia

  DOI：10.1021/acs.orglett.4c00862

  日期：——

  An efficient method for remote radical C(sp3)–H azidation at unactivated sites is described. C–H functionalization proceeds via intramolecular 1,5-hydrogen atom transfer to N-centered radicals that are generated via azido group transfer and/or fragmentation. The readily installed sulfamoyl azide serves as both an amidyl radical precursor and an azido source. This reaction features excellent site selectivity

  描述了一种在未激活位点进行远程自由基 C(sp 3 )–H 叠氮化的有效方法。 C-H 官能化通过分子内 1,5-氢原子转移到通过叠氮基转移和/或断裂产生的 N 中心自由基进行。易于安装的氨磺酰叠氮既充当酰胺自由基前体又充当叠氮源。该反应对叔、仲、伯和苄基 C(sp 3 )–H 键具有出色的位点选择性，并表现出广泛的官能团兼容性。
• Polyamine Analogues of 3β-[N-(N′,N′-Dimethylaminoethane)carbamoyl]cholesterol (DC-Chol) as Agents for Gene Delivery
  作者：Robert G. Cooper、Christopher J. Etheridge、Luisa Stewart、John Marshall、Samantha Rudginsky、Seng H. Cheng、Andrew D. Miller

  DOI：10.1002/(sici)1521-3765(199801)4:1<137::aid-chem137>3.0.co;2-2

  日期：1998.1

  Cationic liposomes are rapidly proving very effective at mediating the delivery of genes to cells in vitro. Moreover, the use of cationic liposomes for gene delivery in vivo is now under consideration. In previous work, we were able to demonstrate that cationic liposomes, formulated from 3 beta-[N-(N',N'-dimethylaminoethane)carbamoyl]cholesterol (DC-Chol) and the neutral phospholipid, dioleoyl L-alpha-phosphatidylethanolamine (DOPE), were able to transfect the lungs of mice in vivo. However, it rapidly became apparent that substantial improvements in the gene delivery efficiency, by approximately two orders of magnitude, would be needed for human lung transfection to be possible. In the following paper we describe the synthesis of a range of polyamine analogues of DC-Chol, which were formulated into cationic liposomes with DOPE and evaluated for efficiency of gene delivery in vitro and in vivo in mice. We report that cationic liposomes formulated from DOPE and the novel pentamine N-15-cholesteryloxycarbonyl-3,7,12-triazapentadecane-1,15-diamine (CTAP) were 100 times more efficient than DC-Chol/DOPE liposomes at gene delivery in vivo (500 times more effective than DNA alone). Therefore, we believe that CTAP/DOPE cationic liposomes should have clinical applications in human gene therapy approaches to the treatment of lung disorders as well as to other clinical conditions.
• An efficient and practical method for the synthesis of mono-N-protected α,ω-diaminoalkanes
  作者：Jae Wook Lee、Sung Im Jun、Kimoon Kim

  DOI：10.1016/s0040-4039(01)00282-9

  日期：2001.4

  The large-scale synthesis of mono-N-protected (Cbz, Boc, Ts, and Ns) alpha,omega -diaminoalkanes (the number of carbon atoms = 3, 4, 5 and 6) are accomplished in 81-945 yield by the protection of amine and subsequent reduction of an azido group from alpha,omega -azido alkyl amines. alpha,omega -Azido alkyl amines are prepared efficiently by the partial reduction of alpha,omega -diazidoalkanes which are obtained from the corresponding dibromoalkanes. (C) 2001 Elsevier Science Ltd. All rights reserved.
• GOLDING, BERNARD T.;OSULLIVAN, MARY C.;SMITH, LEWIS L., TETRAHEDRON LETT., 29,(1988) N 50, C. 6651-6654
  作者：GOLDING, BERNARD T.、OSULLIVAN, MARY C.、SMITH, LEWIS L.

  DOI：——

  日期：——
• Study on the Structure Activity Relationships of NPTX-594, a Spider Toxin Belonging to the Type-B Acylpolyamine Structure
  作者：Tateaki Wakamiya、Tomohiko Kinoshita、Yoshihide Hattori、Yoshihiro Yamaguchi、Hideo Naoki、Gerardo Corzo、Terumi Nakajima

  DOI：10.1246/bcsj.77.331

  日期：2004.2

  In order to elucidate the structure activity relationships of the spider toxin termed NPTX-594, eleven toxin analogs were designed and synthesized, and their paralytic activities against cricket we...

  为了阐明被称为 NPTX-594 的蜘蛛毒素的构效关系，设计并合成了 11 种毒素类似物，以及它们对蟋蟀的麻痹活性...