(R)-(+)-1,2-环氧基十六烷 | 69097-51-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: (R)-(+)-1,2-环氧基十六烷
• 英文名称: (2R)-1,2-epoxyhexadecane
• 英文别名: (2R)-2-tetradecyloxirane；(R)-2-tetradecyloxirane；(R)-1,2-epoxyhexadecane；(R)-(+)-1,2-Epoxyhexadecane
• CAS: 69097-51-4
• 化学式: C₁₆H₃₂O
• 分子量: 240.429
• InChiKey: DSZTYVZOIUIIGA-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  17
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(+)-1,2-环氧基十六烷 在 水 作用下， 以78%的产率得到(R)-1,2-十六烷二醇
  参考文献：
  名称：

  Syntheses and interfacial behaviour of neoglycolipid analogues of glycosyl ceramides

  摘要：

  Four glycosyl ceramides analogues having D-galactose or 2-acetamido-2-deoxy-D-glucose moieties linked to enantiomeric lipids have been synthesised to study their interfacial behaviour at the air \ water interface. The lipid chains were prepared in two steps by opening 1,2-epoxyhexadecane using Jacobsen kinetic hydrolytic resolution (KHR) followed by an azidosilylation reaction of the diol so obtained. Glycosylation reactions were realised either with 2,3,4,6-tetra-O-benzoyl-alpha -D-galactopyranosyl trichloroacetimidate or 1,3,4,6-tetra-O-acetyl-2-allyloxycarbonylamino-2-deoxy-beta -D-glucopyranose as donors and (2R)- or (2S)-2-azidohexadecanol derivatives as acceptors. Transformation of the azido glycosides into N-acylated products was done by a modified Staudinger reaction in the presence of fatty acyl chlorides. The four neoglycolipids are able to form a condensed monolayer at the air \ water interface; their pi -A isotherm diagrams are similar to that described for the natural glycosyl ceramides. The detailed analysis of the isotherms, taking into account the chirality of the lipid chains, allowed to determine the contribution of the different parts of the molecule under the monolayer packing. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00255-5
• 作为产物：
  描述：

  十六碳烯 在 马来酸酐 、 [InCl3(Co((R,R)-C6H10(NCHC6H2O(tert-butyl)2)2))2] 、 水 、 过氧化脲素 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 44.0h， 生成 (R)-(+)-1,2-环氧基十六烷
  参考文献：
  名称：

  （2S，3R，5R）-2-叠氮基-3,5-二羟基十八碳烯鞘脂类似物的合成

  摘要：

  简明和高效地合成了烯乙摩尔类似物。合成策略以Jacobsen的水解动力学拆分（HKR）和炔基硼烷的环氧化物开环为关键步骤。

  DOI：

  10.1055/s-0040-1707397

文献信息

• Synthesis of (Z)-(2′R)-1-O-(2′-methoxynonadec-10′-enyl)-sn-glycerol, a new analog of bioactive ether lipids
  作者：René Momha、Dieudonné Emmanuel Pegnyemb、Paul Mosset

  DOI：10.1016/j.tet.2012.02.033

  日期：2012.4

  (Z)-(2′R)-1-O-(2′-methoxynonadec-10′-enyl)-sn-glycerol, a new analog of bioactive ether lipids, was synthesized from oleic acid and 2,3-isopropylidene-sn-glycerol. The two key steps of this synthesis were the conversion of oleyl aldehyde to a monounsaturated epoxide using Matteson’s method followed by hydrolytic kinetic resolution and a nucleophilic epoxide opening by 2,3-isopropylidene-sn-glycerol in the presence

  不饱和2-甲氧基取代的1- Ö -alkylglycerol，（ž） - （2' - [R）-1- ø - （2'- methoxynonadec-10'-烯基） - SN -甘油，新的生物活性醚脂质的模拟由油酸和2，3-异亚丙基-sn-甘油合成。该合成的两个关键步骤是使用Matteson方法将油醛醛转化为单不饱和环氧化物，然后进行水解动力学拆分，并在叔酸钾存在下通过2,3-异亚丙基-sn-甘油打开亲核环氧化物-无水DMF中的-丁醇盐，似乎是用于此目的的良好试剂。此外，HKR方法的二醇副产物也很容易转化回起始环氧化物，因此几乎使目标分子的量增加了一倍。
• Asymmetric synthesis of (2R)- and (2S)-2-iodohexadecanal, natural inhibitors of the thyroid gland metabolism
  作者：Claude Jacoby、Jean-Claude Braekman、Désiré Daloze

  DOI：10.1016/0040-4020(96)00582-0

  日期：1996.7

  (2R)-(+)- and (2S)-(−)-2-iodohexadecanal 1 with ee's ≥ 89% were synthesized in five steps and 62% overall yield from chiral enol ethers , via the iodocyclization with IC1 and chromatographic separation of the resulting diastereomeric 1′-iododioxanes 8. The ee's of have been determined after their transformation to the (R)-O-methylmandelate esters 11 and 12 or to the epoxides , respectively. Their absolute

  ee≥89 ％的（2 R）-（+）-和（2 S）-（-）-2-碘六癸醛1通过手性烯醇醚的五步合成，通过IC1的碘环化和色谱法合成，ee≥89 ％分离所得的非对映异构体1'-碘二恶烷8。在将ee分别转化为（R）-O-甲基扁桃酸酯11和12或环氧化物后，已经确定了ee 。它们的绝对构型已通过与13的化学相关性以及通过将Mosher方法应用于酯15来指定和16分别通过甲醇分解得到，然后衍生化。而且，已经显示出1的生物合成和抑制活性是非立体选择性的。
• AMINOALCOHOL LIPIDOIDS AND USES THEREOF
  申请人：Mahon Kerry Peter

  公开号：US20110293703A1

  公开（公告）日：2011-12-01

  Aminoalcohol lipidoids are prepared by reacting an amine with an epoxide-terminated compound are described. Methods of preparing aminoalcohol lipidoids from commercially available starting materials are also provided. Aminoalcohol lipidoids may be prepared from racemic or stereochemically pure epoxides. Aminoalcohol lipidoids or salts forms thereof are preferably biodegradable and biocompatible and may be used in a variety of drug delivery systems. Given the amino moiety of these aminoalcohol lipidoid compounds, they are particularly suited for the delivery of polynucleotides. Complexes, micelles, liposomes or particles containing the inventive lipidoids and polynucleotide have been prepared. The inventive lipidoids may also be used in preparing microparticles for drug delivery. They are particularly useful in delivering labile agents given their ability to buffer the pH of their surroundings.

  本文描述了通过将胺与环氧末端化合物反应制备氨基醇脂质体的方法。还提供了从商业起始材料制备氨基醇脂质体的方法。氨基醇脂质体可以从外消旋或立体化学纯的环氧化合物制备。氨基醇脂质体或其盐形式最好是可生物降解和生物相容的，并可用于各种药物输送系统。鉴于这些氨基醇脂质体化合物的氨基基团，它们特别适用于多核苷酸的输送。已经制备了包含创新脂质体和多核苷酸的复合物、胶束、脂质体或粒子。创新脂质体也可以用于制备药物输送的微粒。鉴于它们能够缓冲其周围环境的pH值，它们在输送不稳定剂方面特别有用。
• Asymmetric synthesis of (+)-passifloricin A and its 6-epimer
  作者：S. Chandrasekhar、Ch. Rambabu、A. Syamprasad Reddy

  DOI：10.1016/j.tetlet.2008.05.070

  日期：2008.7

  Stereoselective total syntheses of the antiprotozoal natural product (+)-passifloricin A and its C-6 epimer have been achieved in similar to 5% overall yield. The strategy is based on Jacobsen epoxidation, Grubbs' metathesis and an Evans' intramolecular oxa-Michael reaction. (c) 2008 Elsevier Ltd. All rights reserved.
• A convenient resolution of long-chain alkyl epoxides with Jacobsen's salen(Co)III(OAc) catalysts
  作者：Prashant S Savle、Marika J Lamoreaux、John F Berry‡、Richard D Gandour

  DOI：10.1016/s0957-4166(98)00175-x

  日期：1998.6

  Non-racemic terminal long-chain alkyl epoxides are prepared from racemic epoxides and 1 mol% (R,R)- and (S,S)-salen(Co)III catalysts following a modified procedure for kinetic resolution. The ee's for all epoxides (C-10, C-12, C-14, C-16, C-18, C-20) exceed 95% and the chemical yields range from 85% to 95%. (C) 1998 Elsevier Science Ltd. All rights reserved.