4-pivaloylaminobenzyl chloride | 137105-36-3

• 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-pivaloylaminobenzyl chloride
• 英文别名: N-[4-(chloromethyl)phenyl]-2,2-dimethylpropanamide
• CAS: 137105-36-3
• 化学式: C₁₂H₁₆ClNO
• 分子量: 225.718
• InChiKey: GONLWCQOWOWUNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-pivaloylaminobenzyl chloride 在 吡啶 、 selenium(IV) oxide 、 barium hydroxide octahydrate 、 氨 、 戴斯-马丁氧化剂 、 溶剂黄146 、 sodium iodide 、 barium(II) oxide 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 35.5h， 生成 2-(benzyloxycarbonyl)amino-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3,4-bis-O-(4-(pivaloylamino)benzyl)-D-xylo-hexo-5-ulosonamide
  参考文献：
  名称：

  Glucosamine and Glucosamine-6-phosphate Derivatives: Catalytic Cofactor Analogues for the glmS Ribozyme

  摘要：

  Two analogues of glucosamine-6-phosphate (GlcN6P, 1) and five of glucosamine (GlcN, 2) were prepared for evaluation as catalytic cofactors of the glmS ribozyme, a bacterial gene-regulatory RNA that controls cell wall biosynthesis. Glucosamine and allosamine with 3-azido substitutions were prepared by S(N)2 reactions of the respective 1,2,4,6-protected sugars; final acidic hydrolysis afforded the fully deprotected compounds as their TFA salts. A 6-phospho-2-aminoglucolactam (31) was prepared from glucosamine in a 13-step synthesis, which included a late-stage POCl3-phosphorylation. A simple and widely applicable 2-step procedure with the triethylsilyl (TES) protecting group was developed to selectively expose the 6-OH group in N-protected glucosamine analogues, which provided another route to chemical phosphorylation. Mitsunobu chemistry afforded 6-cyano (35) and 6-azido (36) analogues of GlcN-(Cbz), and the selectivity for the 6-position was confirmed by NMR (COSY, HMBC, HMQC) experiments. Compound 36 was converted to the fully deprotected 6-azido-GlcN (37) and 2,6-diaminoglucose (38) analogues. A 2-hydroxylamino glucose (42) analogue was prepared via an oxaziridine (41). Enzymatic phosphorylation of 42 and chemical phosphorylation of its 6-OH precursor (43) were possible, but 42 and the 6-phospho product (44) were unstable under neutral or basic conditions. Chemical phosphorylation of the previously described 2-guanidinyl-glucose (46) afforded its 6-phospho analogue (49) after final deprotection.

  DOI：

  10.1021/jo400192e
• 作为产物：
  描述：

  N-(4-(hydroxymethyl)phenyl)pivalamide 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到4-pivaloylaminobenzyl chloride
  参考文献：
  名称：

  4-Pivaloylaminobenzyl ether, a new temporary protection for hydroxyl functions

  摘要：

  4-Pivaloylaminobenzyl (PAB) group is a new benzyl-type protecting group which can be introduced either by initial introduction of 4-nitrobenzyl group followed by reduction and N-acylation or by the reaction of a hydroxyl compound with the corresponding halogenide or trichloroacetimidate. PAB ethers have higher acid stability than 4-methoxybenzyl ethers but are readily cleaved with DDQ in a manner similar to the latter.

  DOI：

  10.1016/0040-4039(91)80616-e

文献信息

• Method for making devices having dielectric layers with thiosulfate-containing polymers
  申请人：Eastman Kodak Company

  公开号：US10374178B2

  公开（公告）日：2019-08-06

  A semiconductor device can be prepared using a precursor dielectric composition that comprises: (1) a photochemically or thermally crosslinked product of a photocurable or thermally curable thiosulfate-containing polymer that has a Tg of at least 50° C. and that comprises: an organic polymer backbone comprising (a) recurring units comprising pendant thiosulfate groups; and further comprises charge balancing cations, and (2) optionally, an electron-accepting photo sensitizer component. The electronic device can be prepared by independently applying the precursor dielectric composition and an organic semiconductor composition to a substrate to form an applied precursor dielectric composition and an applied organic semiconductor composition, respectively, and subjecting the applied precursor dielectric composition to curing conditions to form a gate dielectric layer that is in physical contact with the applied organic semiconductor composition.

  可以使用前驱体介电组合物制备半导体器件，前驱体介电组合物包括：(1) 光化学或热交联的含硫代硫酸盐聚合物的产物，该聚合物的 Tg 至少为 50°C，并且包括：有机聚合物主链，该聚合物主链包括(a) 包含悬挂硫代硫酸盐基团的循环单元；并且进一步包括电荷平衡阳离子；以及 (2) 可选的电子接受光敏剂成分。电子器件的制备方法是：将前体电介质组合物和有机半导体组合物独立地施加到基底上，以分别形成施加的前体电介质组合物和施加的有机半导体组合物，并将施加的前体电介质组合物置于固化条件下，以形成与施加的有机半导体组合物物理接触的栅极电介质层。
• METHOD FOR MAKING DEVICES HAVING DIELECTRIC LAYERS WITH THIOSULFATE-CONTAINING POLYMERS
  申请人：Eastman Kodak Company

  公开号：US20170222167A1

  公开（公告）日：2017-08-03

  A semiconductor device can be prepared using a precursor dielectric composition that comprises: (1) a photochemically or thermally crosslinked product of a photocurable or thermally curable thiosulfate-containing polymer that has a T g of at least 50° C. and that comprises: an organic polymer backbone comprising (a) recurring units comprising pendant thiosulfate groups; and further comprises charge balancing cations, and (2) optionally, an electron-accepting photo sensitizer component. The electronic device can be prepared by independently applying the precursor dielectric composition and an organic semiconductor composition to a substrate to form an applied precursor dielectric composition and an applied organic semiconductor composition, respectively, and subjecting the applied precursor dielectric composition to curing conditions to form a gate dielectric layer that is in physical contact with the applied organic semiconductor composition.
• 4-Pivaloylaminobenzyl ether, a new temporary protection for hydroxyl functions
  作者：Koichi Fukase、Takuya Yoshimura、Manabu Hashida、Shoichi Kusumoto

  DOI：10.1016/0040-4039(91)80616-e

  日期：1991.8

  4-Pivaloylaminobenzyl (PAB) group is a new benzyl-type protecting group which can be introduced either by initial introduction of 4-nitrobenzyl group followed by reduction and N-acylation or by the reaction of a hydroxyl compound with the corresponding halogenide or trichloroacetimidate. PAB ethers have higher acid stability than 4-methoxybenzyl ethers but are readily cleaved with DDQ in a manner similar to the latter.
• Glucosamine and Glucosamine-6-phosphate Derivatives: Catalytic Cofactor Analogues for the <i>glmS</i> Ribozyme
  作者：Jeffrey J. Posakony、Adrian R. Ferré-D’Amaré

  DOI：10.1021/jo400192e

  日期：2013.5.17

  Two analogues of glucosamine-6-phosphate (GlcN6P, 1) and five of glucosamine (GlcN, 2) were prepared for evaluation as catalytic cofactors of the glmS ribozyme, a bacterial gene-regulatory RNA that controls cell wall biosynthesis. Glucosamine and allosamine with 3-azido substitutions were prepared by S(N)2 reactions of the respective 1,2,4,6-protected sugars; final acidic hydrolysis afforded the fully deprotected compounds as their TFA salts. A 6-phospho-2-aminoglucolactam (31) was prepared from glucosamine in a 13-step synthesis, which included a late-stage POCl3-phosphorylation. A simple and widely applicable 2-step procedure with the triethylsilyl (TES) protecting group was developed to selectively expose the 6-OH group in N-protected glucosamine analogues, which provided another route to chemical phosphorylation. Mitsunobu chemistry afforded 6-cyano (35) and 6-azido (36) analogues of GlcN-(Cbz), and the selectivity for the 6-position was confirmed by NMR (COSY, HMBC, HMQC) experiments. Compound 36 was converted to the fully deprotected 6-azido-GlcN (37) and 2,6-diaminoglucose (38) analogues. A 2-hydroxylamino glucose (42) analogue was prepared via an oxaziridine (41). Enzymatic phosphorylation of 42 and chemical phosphorylation of its 6-OH precursor (43) were possible, but 42 and the 6-phospho product (44) were unstable under neutral or basic conditions. Chemical phosphorylation of the previously described 2-guanidinyl-glucose (46) afforded its 6-phospho analogue (49) after final deprotection.