[10,10-2H2]-4-nitrophenyl octadecanoate | 1357001-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: [10,10-2H2]-4-nitrophenyl octadecanoate
• 英文别名: [10,10-²H2]-4-nitrophenyl octadecanoate；p-nitrophenyl 10,10-dideuteriooctadecanoate
• CAS: 1357001-13-8
• 化学式: C₂₄H₃₉NO₄
• 分子量: 407.562
• InChiKey: HAIZAZONHOVLEK-KNXIQCGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.76
• 重原子数：
  29.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [10,10-2H2]-4-nitrophenyl octadecanoate 、 在 copper(l) iodide 、 nickel(II) chloride hexahydrate 、 四甲基乙二胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 [10,10-²H2]-(2S,3R,E)-(2-(stearoylamino)-3-hydroxyoctadec-4-en-1-yl)-(2-((6-hydroxyhexa-2,4-diyn-1-yl)dimethylammonio)ethyl)phosphate
  参考文献：
  名称：

  Novel Raman-tagged sphingomyelin that closely mimics original raft-forming behavior

  摘要：

  Three Raman probes of sphingomyelin (SM) were synthesized and evaluated for their applicability to imaging experiments. One probe containing a hydroxymethyl-1,3-butadiyne moiety in the polar head group showed strong scattering. The solid-state H-2 NMR spectra of this probe in oriented bilayer membrane revealed excellent compatibility with natural SM in phase behavior since the probe undergoes phase separation to form raft-like liquid ordered (L-o) domains in the raft-mimicking mixed bilayers. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.014
• 作为产物：
  描述：

  [10,10-²H2]-tert-butyl((octadecyl)oxy)diphenylsilane 在 Jones reagent 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 14.17h， 生成 [10,10-2H2]-4-nitrophenyl octadecanoate
  参考文献：
  名称：

  Novel Raman-tagged sphingomyelin that closely mimics original raft-forming behavior

  摘要：

  Three Raman probes of sphingomyelin (SM) were synthesized and evaluated for their applicability to imaging experiments. One probe containing a hydroxymethyl-1,3-butadiyne moiety in the polar head group showed strong scattering. The solid-state H-2 NMR spectra of this probe in oriented bilayer membrane revealed excellent compatibility with natural SM in phase behavior since the probe undergoes phase separation to form raft-like liquid ordered (L-o) domains in the raft-mimicking mixed bilayers. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.014

文献信息

• NMR-based conformational analysis of sphingomyelin in bicelles
  作者：Toshiyuki Yamaguchi、Takashi Suzuki、Tomokazu Yasuda、Tohru Oishi、Nobuaki Matsumori、Michio Murata

  DOI：10.1016/j.bmc.2011.11.001

  日期：2012.1

  Sphingomyelin (SM) is a common sphingolipid in mammalian membranes and is known to be substantially involved in cellular events such as the formation of lipid rafts. Despite its biological significance, conformation of SM in a membrane environment remains unclear because the noncrystalline property and anisotropic environment of lipid bilayers hampers the application of X-ray crystallography and NMR measurements. In this study, to elucidate the conformation of SM in membranes, we utilized bicelles as a substitute for a lipid bilayer membrane. First, we demonstrated through P-31 NMR, H-2 NMR, and dynamic light scattering experiments that SM forms both oriented and isotropic bicelles by changing the ratio of SM/dihexanoyl phosphatidylcholine. Then, we determined the conformation of SM in isotropic bicelles on the basis of coupling constants and NOE correlations in H-1 NMR and found that the C2-C6 and amide groups of SM take a relatively rigid conformation in bicelles. (C) 2011 Elsevier Ltd. All rights reserved.