N-(benzyloxy)pivalamide | 1222972-18-0

• 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: N-(benzyloxy)pivalamide
• 英文别名: 2,2-dimethyl-N-phenylmethoxypropanamide
• CAS: 1222972-18-0
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: XSBZRCYZDXMLPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2-{[(tert-butoxycarbonyl)oxy](phenyl)methyl}acrylate 、 N-(benzyloxy)pivalamide 在 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到methyl 2-((N-(benzyloxy)pivalamido)(phenyl)methyl)acrylate
  参考文献：
  名称：

  α/β-二肽衍生物的催化剂控制区域分散合成通过 O-烷基异羟肟酸酯与 MBH 碳酸酯的 N-烯丙基烷基化反应

  摘要：

  报道了O-烷基异羟肟酸酯与 MBH 碳酸酯的催化剂控制的可切换N-烯丙基反应，为 α/β-二肽衍生物提供了区域发散方法。

  DOI：

  10.1002/asia.202101186
• 作为产物：
  描述：

  苯甲醇 在 N-羟基邻苯二甲酰亚胺 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 3.58h， 生成 N-(benzyloxy)pivalamide
  参考文献：
  名称：

  通过CH活化将苄醇转化为邻氨基苯甲醛：喹唑啉的一种简便方法

  摘要：

  指导基团直接转化为重要的合成单元将为合成化学提供一种高原子效率的合成方法。此处是合成邻氨基苯甲醛和苯并恶唑的便捷方法...

  DOI：

  10.1039/c6cc05560e

文献信息

• Box-copper catalyzed cascade asymmetric amidation for chiral <i>exo</i>-methylene aminoindoline derivatives
  作者：Xiao-Peng Yang、Hao-Peng Lv、Hao-Di Yang、Bai-Lin Wang、Xing-Wang Wang

  DOI：10.1039/d1ob01242h

  日期：——

  transformation was triggered by the attack of hydroxamates to dipolar copper–allenylidene intermediates, followed by a nucleophilic annulation reaction. Thus, a series of exo-methylene 3-aminoindoline derivatives were obtained in good yields with high enantioselectivities under mild reaction conditions.

  在乙炔基苯并恶嗪酮和 α-卤代异羟肟酸酯之间在 indapybox 配体存在下实现了对映选择性铜催化的级联分子间和分子内酰胺化。一锅级联转化是由异羟肟酸盐攻击偶极铜-亚烯基中间体引发的，然后是亲核环化反应。因此，在温和的反应条件下以良好的收率和高对映选择性获得了一系列外-亚甲基3-氨基二氢吲哚衍生物。
• Sunlight‐ or UVA‐Light‐Mediated Synthesis of Hydroxamic Acids from Carboxylic Acids
  作者：Olga G. Mountanea、Christiana Mantzourani、Maroula G. Kokotou、Christoforos G. Kokotos、George Kokotos

  DOI：10.1002/ejoc.202300046

  日期：——

  A sunlight- or UVA-light-mediated synthesis of hydroxamic acids from carboxylic acids and protected hydroxylamines is reported, the key step of which is the formation of a charge transfer complex. Mechanistic studies by DI-HRMS provide experimental evidence for the formation of various intermediates. Two hydroxamic drugs (Vorinostat and Bufexamac) were synthesized.

  报道了阳光或 UVA 光介导的从羧酸和受保护的羟胺合成异羟肟酸的方法，其关键步骤是电荷转移复合物的形成。DI-HRMS 的机理研究为各种中间体的形成提供了实验证据。合成了两种异羟肟酸药物（伏立诺他和布非昔美）。
• Visible-light-promoted N–H functionalization of O-substituted hydroxamic acid with diazo esters
  作者：Shuangshuang Xia、Yongchan Jian、Liwen Zhang、Cheng Zhang、Yuanyuan An、Yubin Wang

  DOI：10.1039/d3ra02407e

  日期：——

  Herein we report an N–H functionalization of O-substituted hydroxamic acid with diazo esters under blue LED irradiation conditions. The present transformations could be performed efficiently under mild conditions without use of catalyst, additive and N2 atmosphere. Interestingly, when THF and 1,4-dioxane were employed as the reaction solvents, an active oxonium ylide involved three-component reaction

  在此，我们报道了在蓝色 LED 照射条件下 O-取代异羟肟酸与重氮酯的 N-H 官能化。在不使用催化剂、添加剂和 N 2气氛的情况下，本转化可以在温和条件下有效地进行。有趣的是，当使用 THF 和 1,4-二恶烷作为反应溶剂时，活性氧鎓叶立德分别涉及三组分反应和卡宾物种向异羟肟酸酯中的 N-H 插入。
• Transition-Metal-Assisted Radical/Radical Cross-Coupling: A New Strategy to the Oxidative C(sp³)–H/N–H Cross-Coupling
  作者：Liangliang Zhou、Shan Tang、Xiaotian Qi、Caitao Lin、Kun Liu、Chao Liu、Yu Lan、Aiwen Lei

  DOI：10.1021/ol501485f

  日期：2014.6.20

  A transition-metal-assisted oxidative C(sp(3))-H/N-H cross-coupling reaction of N-alkoxyamides with aliphatic hydrocarbons is described. During the reaction, nitrogen radicals were generated from the oxidation of N-alkoxyamides. Experiments and DFT calculations revealed that transition-metal catalyst could lower the reactivity of the generated nitrogen radical by the coordination of the transition metal, which allowed the selective radical/radical cross-coupling with the transient sp(3) carbon radical to construct C(sp(3))--N bonds. Various C(sp(3))-H bonds could be transformed into C(sp(3))-N bonds through this radical amidation strategy.
• [EN] DIACYGLYCEROL MIMETICS AND METHODS OF USING THE SAME AS PROTEIN KINASE C ALPHA ACTIVATORS AND APOPTOSIS INDUCERS<br/>[FR] MIMETIQUES DE DIACYLGLYCEROL ET LEURS PROCEDES D'UTILISATION EN TANT QU'ACTIVATEURS DE LA PROTEINE KINASE C ALPHA ET EN TANT QU'INDUCTEURS D'APOPTOSE
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2003013504A1

  公开（公告）日：2003-02-20

  Disclosed herein are methods for inducing apoptosis by exposing cells to an apoptic inducing amount of one or more of newly created DAG-lactone mimetics. In one embodiment of the new class of DAG compounds the new DAG-mimetic compound satisfies general formula (I) as follows:, wherein R1, R2, R3, and R4 are independently selected from the group consisting essentially of hydrogen, oxygen, nitrogen, hydroxyls, halogens, branched or unbranched, substituted or unsubstituted, aliphatic groups, heteroatom (e.g., O, S, N, hydroxyls, halogens) substituted aliphatic groups, aromatic groups, and all major functional groups. Preferably, R1 is O and R3 is a hydroxyalkyl such as CH2OH. Also preferably, R2 is an alkylidene group derived from an aldehyde and R4 is an alkyl group derived from an acid chloride. The size of the lactone ring may be varied by either increasing or decreasing the ring size. Preferably, R1, R2, R3, and R4 when comprising carbon chains or rings, comprise groups of carbon chains or rings of 12 carbon atoms or less.