benzyl ((tert-butoxycarbonyl)oxy)carbamate | 1138083-43-8

• 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: benzyl ((tert-butoxycarbonyl)oxy)carbamate
• 英文别名: Tert-butyl phenylmethoxycarbonylamino carbonate
• CAS: 1138083-43-8
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: NECBPWWKKLFFLA-UHFFFAOYSA-N

物化性质

• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl ((tert-butoxycarbonyl)oxy)carbamate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 偶氮二甲酸二异丙酯 、 (11aR)-(+)-10,11,12,13-tetrahydrodiindeno-[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 123.0h， 生成 (2R)-(+)-phenylmethyl 2-vinylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  N-（甲苯磺酰氧基）氨基甲酸酯的对映选择性 Aza-Heck 环化：吡咯烷和哌啶的合成

  摘要：

  用 SPINOL 衍生的氨基磷酸酯配体修饰的 Pd(0)-系统促进烯基 N-（甲苯磺酰氧基）氨基甲酸酯的高度对映选择性 aza-Heck 环化。该方法提供了对具有挑战性的 N-杂环的通用访问，并代表了迄今为止开发的最广泛的对映选择性 aza-Heck 协议。

  DOI：

  10.1021/jacs.8b12689
• 作为产物：
  描述：

  N-(苄羰氧基)羟基胺 、 二碳酸二叔丁酯 在 sodium t-butanolate 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl ((tert-butoxycarbonyl)oxy)carbamate
  参考文献：
  名称：

  Kinetics of Action of a Two-Stage Pro-Inhibitor of Serine β-Lactamases

  摘要：

  beta-Lactamase inhibitors are important in medicine in the protection of beta-lactam antibiotics from beta-lactamase-catalyzed destruction. The most effective inhibitors of serine beta-lactamases covalently modify the enzyme active site. We have recently studied O-acyl and O-phosphyl hydroxamates as a new class of such inhibitors. In this paper, we describe our studies of the N-acyl derivatives of a cyclic O-acyl hydroxamic acid, 3H-benzo[d][1,2]oxazine-1,4-dione, and, in particular, the N-tert-butoxycarbonyl derivative. This compound is not a beta-lactamase inhibitor itself but undergoes spontaneous hydrolysis in aqueous solution, yielding an O-phthaloyl hydroxamic acid, which is a beta-lactamase inhibitor. This compound spontaneously, but reversibly, cyclizes in solution to form phthalic anhydride, which is also a beta-lactamase inhibitor. Both inhibitors react to form the same transiently stable phthaloyl-enzyme complex. Thus, we have a two-step cascade, beginning with a pro-inhibitor, in which each step leads to a different inhibitor, presumably with different enzyme specificities. The kinetics of these transformations have been elucidated in detail. The phthaloyl derivatives, where the free carboxylate is important for facile reaction with the enzyme, represent a new lead for serine beta-lactamase inhibitors. Analogues can be conveniently constructed in situ by reaction of nucleophiles with phthalic anhydrides and then screened for activity. Active hits may then become new leads.

  DOI：

  10.1021/bi400873r

文献信息

• Design, synthesis, and evaluation of a novel bridged nucleic acid, 2′,5′-BNAON, with S-type sugar conformation fixed by N–O linkage
  作者：Tetsuya Kodama、Chieko Matsuo、Hidetsugu Ori、Tetsuya Miyoshi、Satoshi Obika、Kazuyuki Miyashita、Takeshi Imanishi

  DOI：10.1016/j.tet.2008.12.073

  日期：2009.3

  We designed a novel 2′-O,5′-N bridged nucleic acid, 2′,5′-BNAON, whose sugar puckering was fixed to S-type conformation by an N–O linkage. A dimer unit formed from 2′,5′-BNAON-U and thymidine was synthesized via a coupling reaction between a protected 2′,5′-BNAON-U monomer and a thymidine derivative. Introduction of 2′,5′-BNAON-U into DNA was carried out using conventional phosphoramidite chemistry

  我们设计了一种新型的2' - O，5'- N桥接核酸2'，5'-BNA ON，其糖折叠通过N - O键固定在S型构象上。通过受保护的2'，5'-BNA ON -U单体与胸苷衍生物之间的偶联反应，合成了由2'，5'-BNA ON -U和胸苷形成的二聚体单元。使用常规的亚磷酰胺化学和DNA合成仪将2'，5'-BNA ON -U引入DNA。评价了2'，5'-BNA ON -U-修饰的寡核苷酸对DNA或RNA补体的杂交能力。
• Access to Chiral Chromenones through Organocatalyzed Mannich/Annulation Sequence
  作者：Jingxiang Duan、Zongli Xiong、Yuqiao Zhou、Weijun Yao、Xiaoyi Li、Min Zhang、Zhen Wang

  DOI：10.1021/acs.orglett.1c03010

  日期：2021.10.15
• Kinetics of Action of a Two-Stage Pro-Inhibitor of Serine β-Lactamases
  作者：Ronak Tilvawala、R. F. Pratt

  DOI：10.1021/bi400873r

  日期：2013.10.8

  beta-Lactamase inhibitors are important in medicine in the protection of beta-lactam antibiotics from beta-lactamase-catalyzed destruction. The most effective inhibitors of serine beta-lactamases covalently modify the enzyme active site. We have recently studied O-acyl and O-phosphyl hydroxamates as a new class of such inhibitors. In this paper, we describe our studies of the N-acyl derivatives of a cyclic O-acyl hydroxamic acid, 3H-benzo[d][1,2]oxazine-1,4-dione, and, in particular, the N-tert-butoxycarbonyl derivative. This compound is not a beta-lactamase inhibitor itself but undergoes spontaneous hydrolysis in aqueous solution, yielding an O-phthaloyl hydroxamic acid, which is a beta-lactamase inhibitor. This compound spontaneously, but reversibly, cyclizes in solution to form phthalic anhydride, which is also a beta-lactamase inhibitor. Both inhibitors react to form the same transiently stable phthaloyl-enzyme complex. Thus, we have a two-step cascade, beginning with a pro-inhibitor, in which each step leads to a different inhibitor, presumably with different enzyme specificities. The kinetics of these transformations have been elucidated in detail. The phthaloyl derivatives, where the free carboxylate is important for facile reaction with the enzyme, represent a new lead for serine beta-lactamase inhibitors. Analogues can be conveniently constructed in situ by reaction of nucleophiles with phthalic anhydrides and then screened for activity. Active hits may then become new leads.
• Enantioselective Aza-Heck Cyclizations of <i>N</i>-(Tosyloxy)carbamates: Synthesis of Pyrrolidines and Piperidines
  作者：Xiaofeng Ma、Ian R. Hazelden、Thomas Langer、Rachel H. Munday、John F. Bower

  DOI：10.1021/jacs.8b12689

  日期：2019.2.27

  Pd(0)-systems modified with SPINOL-derived phosphoramidate ligands promote highly enantioselective aza-Heck cyclizations of alkenyl N-(tosyloxy)carbamates. The method provides versatile access to challenging N-heterocycles and represents the broadest scope enantioselective aza-Heck protocol developed to date.

  用 SPINOL 衍生的氨基磷酸酯配体修饰的 Pd(0)-系统促进烯基 N-（甲苯磺酰氧基）氨基甲酸酯的高度对映选择性 aza-Heck 环化。该方法提供了对具有挑战性的 N-杂环的通用访问，并代表了迄今为止开发的最广泛的对映选择性 aza-Heck 协议。