tert-butyl N-[2-(2-cyanoethylamino)ethyl]carbamate | 1019333-23-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl N-[2-(2-cyanoethylamino)ethyl]carbamate
• CAS: 1019333-23-3
• 化学式: C₁₀H₁₉N₃O₂
• 分子量: 213.28
• InChiKey: FAOXXOIHVZGLFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  74.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-(2-cyanoethylamino)ethyl]carbamate 在 palladium on activated charcoal 锂硼氢 、 三甲基氯硅烷 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 20.5h， 生成
  参考文献：
  名称：

  非共价肽-三吡咯共轭物的序列特异性DNA结合。

  摘要：

  DOI：

  10.1002/anie.200603115
• 作为产物：
  描述：

  二碳酸二叔丁酯 以 甲醇 、 氯仿 为溶剂， 反应 28.0h， 生成 tert-butyl N-[2-(2-cyanoethylamino)ethyl]carbamate
  参考文献：
  名称：

  A ribozyme with michaelase activity

  摘要：

  The ability to generate RNA molecules that can catalyze complex organic transformations not only facilitates the reconstruction and plausibility of possible prebiotic reaction pathways but is also crucial for elucidating the potential of the application of RNA catalysts in organic syntheses. Iterative RNA selection previously identified a ribozyme that catalyzes the Michael addition of a cysteine thiol to an alpha,beta-unsaturated amide. This reaction is chemically similar to the rate limiting step of the thymidylate synthase reaction, which is the corresponding reaction of a cysteine thiol to the double-bond of the uracil nucleobase. Here we provide a detailed description of the synthesis of the ribozyme substrates and the substrate oligonucleotides used for its characterization and the investigation of the background reaction. We also describe the further characterization of the ribozyme with respect to substrate specificity. We show that the thiol group of the cysteine nucleophile is essential for the reaction to proceed. When substituted for a thiomethyl group, no reaction takes place. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00311-5

文献信息

• Facile Synthetic Route to Selectively Protected Spermidine Homologues
  作者：Ryszard Andruszkiewicz、Ewa Gronek、Jolanta Hałuszczak

  DOI：10.1080/00397910701845431

  日期：2008.2.1

  Abstract Several selectively protected spermidine homologues were synthesized via cyanoethylation reaction of monoprotected diamines, subsequent protection of their secondary amino group, hydrolysis of nitrile to primary amide function, and final Hofmann degradation of amides to amines with the aid of iodosobenzene diacetate (PIDA). The protected spermidine homologues may be directly used in the synthesis

  摘要 通过单保护二胺的氰乙基化反应、仲氨基的后续保护、腈水解为伯酰胺官能团以及酰胺在二乙酸碘苯酯 (PIDA) 的帮助下最终霍夫曼降解为胺，合成了几种选择性保护的亚精胺同系物。受保护的亚精胺同系物可直接用于多胺酰胺的合成或可进一步官能化。
• Allgemeiner Zugang zu Polyaminen mit Ethan‐1,2‐diamin‐Einheiten: Synthese von nicht natürlich vorkommenden homologen und isomeren <i>N</i> ¹ ,4‐Di(4‐cumaroyl)sperminen
  作者：Martin Lochner、Hervé Geneste、Manfred Hesse

  DOI：10.1002/(sici)1522-2675(19981216)81:12<2270::aid-hlca2270>3.0.co;2-#

  日期：1998.12.16
• A ribozyme with michaelase activity
  作者：Alexander Eisenführ、Paramjit S Arora、Gerhard Sengle、Leo R Takaoka、James S Nowick、Michael Famulok

  DOI：10.1016/s0968-0896(02)00311-5

  日期：2003.1

  The ability to generate RNA molecules that can catalyze complex organic transformations not only facilitates the reconstruction and plausibility of possible prebiotic reaction pathways but is also crucial for elucidating the potential of the application of RNA catalysts in organic syntheses. Iterative RNA selection previously identified a ribozyme that catalyzes the Michael addition of a cysteine thiol to an alpha,beta-unsaturated amide. This reaction is chemically similar to the rate limiting step of the thymidylate synthase reaction, which is the corresponding reaction of a cysteine thiol to the double-bond of the uracil nucleobase. Here we provide a detailed description of the synthesis of the ribozyme substrates and the substrate oligonucleotides used for its characterization and the investigation of the background reaction. We also describe the further characterization of the ribozyme with respect to substrate specificity. We show that the thiol group of the cysteine nucleophile is essential for the reaction to proceed. When substituted for a thiomethyl group, no reaction takes place. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Sequence-Specific DNA Binding by Noncovalent Peptide–Tripyrrole Conjugates
  作者：Juan B. Blanco、Verónica I. Dodero、M. Eugenio Vázquez、Manuel Mosquera、Luis Castedo、José L. Mascareñas

  DOI：10.1002/anie.200603115

  日期：2006.12.11