methyl 16-iodohexadecanoate | 106689-05-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 16-iodohexadecanoate
• CAS: 106689-05-8
• 化学式: C₁₇H₃₃IO₂
• 分子量: 396.352
• InChiKey: FOHXUGJFBSGTCP-UHFFFAOYSA-N

物化性质

• 沸点：
  400.2±18.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 16-iodohexadecanoate 在 1,5,7-三氮杂双环[4.4.0]癸-5-烯 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 methyl 16-[[(3aS,5R,6S,7S,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d][1,3]oxazol-2-yl]sulfanyl]hexadecanoate
  参考文献：
  名称：

  Conformationally-locked N-glycosides: Exploiting long-range non-glycone interactions in the design of pharmacological chaperones for Gaucher disease

  摘要：

  Pyranoid-type glycomimetics having a cis-1,2-fused glucopyranose-2-alkylsulfany1-1,3-oxazoline (Glc-PSO) structure exhibit an unprecedented specificity as inhibitors of mammalian beta-glucosidase. Notably, their inhibitory potency against human beta-glucocerebrosidase (GCase) was found to be strongly dependent on the nature of aglycone-type moieties attached at the sulfur atom. In the particular case of omega-substituted hexadecyl chains, an amazing influence of the terminal group was observed. A comparative study on a series of Glc-PSO derivatives suggests that hydrogen bond acceptor functionalities, e.g. fluoro or methyloxycarbonyl, significantly stabilize the Glc-PSO:GCase complex. The S-(16-fluorohexadecyl)-PSO glycomimetic turned out to be a more potent GCase competitive inhibitor than ambroxol, a non glycomimetic drug currently in pilot trials as a pharmacological chaperone for Gaucher disease. Moreover, the inhibition constant increased by one order of magnitude when shifting from neutral (pH 7) to acidic (pH 5) media, a favorable characteristic for a chaperone candidate. Indeed, the fluoro-PSO derivative also proved superior to ambroxol in mutant GCase activity enhancement assays in N370S/N370S Gaucher fibroblasts. The results presented here represent a proof of concept of the potential of exploiting long-range non-glycone interactions for the optimization of glycosidase inhibitors with chaperone activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.002
• 作为产物：
  描述：

  16-羟基棕榈酸 在 氢溴酸 、 溶剂黄146 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 40.0h， 生成 methyl 16-iodohexadecanoate
  参考文献：
  名称：

  Kling, Marcel R.; Easton, Christopher J.; Poulos, Alf, Journal of the Chemical Society. Perkin transactions I, 1993, # 10, p. 1183 - 1190

  摘要：

  DOI：

文献信息

• Identification of very long chain unsaturated fatty acids from Ximenia oil by atmospheric pressure chemical ionization liquid chromatography–mass spectroscopy
  作者：Tomáš Řezanka、Karel Sigler

  DOI：10.1016/j.phytochem.2006.11.034

  日期：2007.3

  A method is described for the enrichment of very long chain unsaturated fatty acids from total fatty acids of Ximenia oil and their identification as picolinyl esters by means of liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization (LC-MS/APCI). The method is based on the use of preparative reversed phase HPLC and their subsequent identification by microbore LC-MS/APCI

  描述了一种从西梅尼亚油总脂肪酸中富集极长链不饱和脂肪酸的方法，并通过液相色谱-质谱联用常压化学电离 (LC-MS/APCI) 将其鉴定为吡啶甲基酯。该方法基于使用制备型反相 HPLC 及其随后通过微孔 LC-MS/APCI 进行的鉴定。这两种技术的组合被用来识别不寻常的不饱和 VLCFAs，最高可达 tetracontenoic 酸。还合成了四十三碳烯酸的所有四种位置异构体以明确确认它们的结构。
• Polyfluoroglycoside Synthesis via Simple Alkylation of an Anomeric Hydroxyl Group: Access to Fluoroetoposide Analogues
  作者：Thomas Tremblay、Jacob St-Gelais、Maxime Houde、Denis Giguère

  DOI：10.1021/acs.joc.0c02841

  日期：2021.3.19

  analogues. This strategy used a simple alkylation protocol and allowed the installation of a simple aglyconic alkane with the β configuration. Moreover, the glycosylation of fluorinated glucoside analogues with 4′-demethylepipodophyllotoxin furnished novel fluoroetoposide analogues. In these cases, the α anomers were formed as major products with an S configuration at the C-4 of the aglycone.

  在这项工作中，我们开发了一种合成氟糖苷类似物的新方法。该策略使用简单的烷基化方案，并允许安装具有β构型的简单无糖链烷烃。此外，氟化葡萄糖苷类似物与4'-脱甲基表鬼臼毒素的糖基化提供了新颖的氟依托泊苷类似物。在这些情况下，形成的α端基异构体是在糖苷配基的C-4处具有S构型的主要产物。
• Highly Terminal-Selective Epoxidation of Linolenic Acid with an Amphiphilic Iron Porphyrin Catalyst Casted in Bilayer Membranes
  作者：Yoshinori Naruta、Masa-oki Goto、Toshifumi Tawara、Fumito Tani

  DOI：10.1246/cl.2002.162

  日期：2002.2

  An amphiphilic iron porphyrin having four hexadecanoic acid chains on each face of the porphyrin was prepared and the catalytic epoxidation of linolenic acid with the heme-casted bilayer membranes was achieved in high regioselectivity at the terminal double bond of the substrate. The orientation of the porphyrin ring in the membrane was determined to be parallel to the aqueous-bilayer interface by means of ESR.

  制备了一种两亲性铁卟啉，卟啉的每个面上都有四条十六烷酸链，用这种血红素浇铸的双层膜催化亚麻酸的环氧化反应，在底物的末端双键处实现了高区域选择性。通过 ESR，确定了膜中卟啉环的取向与水层界面平行。
• Initiation and bonding of diamond and other thin films
  申请人：Bension, Rouvain M.

  公开号：EP0598361A1

  公开（公告）日：1994-05-25

  A method for initiating and bonding thin films on substrates is described. The method employs an interlayer comprising a self-assembling monolayer (SAM). The SAM is formed from monomers, one end of which are capable of bonding to the substrate, and the other end of which form a surface similar to, and capable of initiating the formation of a film. Additionally, compositions for monomers, methods for SAM formation, and methods for film formation are disclosed. In a preferred embodiment the thin film is comprised of diamond.

  本发明涉及一种在基板上启动和结合薄膜的方法。该方法采用包含自组装单层（SAM）的中间层。SAM由单体形成，其中一端能够与基板结合，另一端形成类似于表面，并能够启动膜的形成。此外，还公开了单体的组成，SAM形成的方法以及膜形成的方法。在优选实施例中，薄膜由金刚石组成。
• Kling, Marcel R.; Easton, Christopher J.; Poulos, Alf, Journal of the Chemical Society. Perkin transactions I, 1993, # 10, p. 1183 - 1190
  作者：Kling, Marcel R.、Easton, Christopher J.、Poulos, Alf

  DOI：——

  日期：——