1-chloro-10-(2-naphthyl)-3,6,9-trioxadecane | 741677-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-chloro-10-(2-naphthyl)-3,6,9-trioxadecane
• 英文别名: 2-[2-[2-(2-chloroethoxy)ethoxy]ethoxymethyl]naphthalene
• CAS: 741677-97-4
• 化学式: C₁₇H₂₁ClO₃
• 分子量: 308.805
• InChiKey: IFIJENPNRQNOHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-chloro-10-(2-naphthyl)-3,6,9-trioxadecane 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 水 、 四氯化锡 、 sodium hydride 、 苯硫酚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 26.33h， 生成 2,3,4-tri-O-acetyl-6-O-(10-[2-naphthyl]-3,6,9-trioxadecanyl)-α-D-galactopyranose
  参考文献：
  名称：

  Rational Design, Synthesis, and Characterization of Novel Inhibitors for Human β1,4-Galactosyltransferase

  摘要：

  An affinity labeling reagent, uridine 5'-(6-amino-{2-[(7-bromomethyl-2-naphthyl)methoxy-carbonylmethoxy]ethoxy}acetyl-6-deoxy-alpha-D-galactopyranosyl) diphosphate (1a), was designed on the basis of 3D docking simulation and synthesized to investigate the functional role of Trp310 residue located in the small loop near the active site of human recombinant galactosyltransferase (beta GalT-1). Mass spectrometric analysis revealed that the Trp310 residue of beta GalT1 can be selectively modified with the naphthylmethyl group of compound la at the C-3 position of the indole ring. This result motivated us to synthesize novel uridine-5'-diphosphogalactose (UDP-Gal) analogues as candidates for mechanism-based inhibitors for beta GalT-1. We found that uridine 5'-(6-O-[10-(2-naphthyl)-3,6,9-trioxadecanyl]-alpha-D-galactopyranosyl) diphosphate (2) is the strongest inhibitor (K-i = 1.86 mu M) against UDP-Gal (K-m = 4.91 mu M) among compounds reported previously. A cold spray ionization time-of-flight mass spectrometry study demonstrated that the complex of this inhibitor and beta GalT-1 cannot interact with an acceptor substrate in the presence of Mn2+.

  DOI：

  10.1021/jm0504297
• 作为产物：
  描述：

  2-溴甲基萘 在 吡啶 、 氯化亚砜 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 1-chloro-10-(2-naphthyl)-3,6,9-trioxadecane
  参考文献：
  名称：

  Rational Design, Synthesis, and Characterization of Novel Inhibitors for Human β1,4-Galactosyltransferase

  摘要：

  An affinity labeling reagent, uridine 5'-(6-amino-{2-[(7-bromomethyl-2-naphthyl)methoxy-carbonylmethoxy]ethoxy}acetyl-6-deoxy-alpha-D-galactopyranosyl) diphosphate (1a), was designed on the basis of 3D docking simulation and synthesized to investigate the functional role of Trp310 residue located in the small loop near the active site of human recombinant galactosyltransferase (beta GalT-1). Mass spectrometric analysis revealed that the Trp310 residue of beta GalT1 can be selectively modified with the naphthylmethyl group of compound la at the C-3 position of the indole ring. This result motivated us to synthesize novel uridine-5'-diphosphogalactose (UDP-Gal) analogues as candidates for mechanism-based inhibitors for beta GalT-1. We found that uridine 5'-(6-O-[10-(2-naphthyl)-3,6,9-trioxadecanyl]-alpha-D-galactopyranosyl) diphosphate (2) is the strongest inhibitor (K-i = 1.86 mu M) against UDP-Gal (K-m = 4.91 mu M) among compounds reported previously. A cold spray ionization time-of-flight mass spectrometry study demonstrated that the complex of this inhibitor and beta GalT-1 cannot interact with an acceptor substrate in the presence of Mn2+.

  DOI：

  10.1021/jm0504297

文献信息

• Esterification and Etherification of Aliphatic Alcohols Enabled by Catalytic Strain-Release of Donor–Acceptor Cyclopropane
  作者：Dan Yang、Han Ding、Xiao-Lin Zhang、Huajun Zhang、Yuhan Zhang、Xue-Wei Liu

  DOI：10.1021/acs.orglett.4c01637

  日期：2024.6.14

  esterification and etherification of alcohols, leveraging a Sc(OTf)3-catalyzed ring-strain release event in the meticulously designed, chromatographically stable mixed anhydrides or benzyl esters that incorporate an intramolecular donor–acceptor cyclopropane (DAC). This versatile method facilitates the straightforward functionalization of sugar, terpene, and steroid alcohols under mild acidic conditions,

  我们在此公开了一种用于醇的酯化和醚化的高效方案，利用 Sc(OTf) 3催化的环应变释放事件，在精心设计的、色谱稳定的混合酸酐或苄酯中结合了分子内供体-受体环丙烷（数模转换器）。这种多功能方法有利于糖、萜烯和类固醇醇在温和酸性条件下的直接官能化，正如糖二醇的单催化剂驱动的双重保护所证明的那样。