1-O-(1'-hexadecenyl)-rac-glycerol | 56194-19-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1-O-(1'-hexadecenyl)-rac-glycerol
• 英文别名: 1-O-1'-(Z)-hexadecenyl-glycerol；3-hexadec-1-en-c-yloxy-propane-1,2-diol；3--propan-1.2-diol；(+/-)-cis-O¹-Hexadec-1-enyl-glycerin；cis-1-O-(Hexadec-1-enyl)-sn-glycerol；3-[(Z)-hexadec-1-enoxy]propane-1,2-diol
• CAS: 56194-19-5
• 化学式: C₁₉H₃₈O₃
• 分子量: 314.509
• InChiKey: CBTIUALKZHXQNM-NXVVXOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  22
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-O-(1'-hexadecenyl)-rac-glycerol 在 吡啶 、 咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 3-tert-butyldiphenylsilyl-2-hexadecanoyl-1-O-(1'-(Z)-hexadecenyl)-rac-glycerol
  参考文献：
  名称：

  Stereocontrolled Synthesis of Plasmalogen-Type Lipids from Glyceryl Ester Precursors

  摘要：

  Two pathways for the synthesis of naturally occurring Z vinyl ether linkages in plasmalogen lipids (1-O-((Z)-1'-alkenyl)-2-acyl-sn-glycerophosphocholines and ethanolamines) have been investigated: (i) reduction of alpha-alkoxy enol phosphates and (ii) alkylidenation of diprotected glyceryl 1-formate esters utilizing 1,1-dibromoalkanes, zinc, TiCl4, and TMEDA. While both methods reported good chemical yields and high Z selectivity for model substrates, the titanium-mediated coupling sequence failed when the dibromoalkyl chain length exceeded Ca, Treatment of 1-decyl-2-O-benzyl-3-O-(tert-butyldiphenylsilyl) with LDA and diethyl chlorophosphate at -78 degrees C followed by reduction of the vinyl phosphate intermediate using Pd(PPh(3))4 and Et(3)Al in DCE at 0 degrees C, however, gave 1-O-(1'-decenyl)2-O-benzyl-3-O-(tert-butyldiphenylsilyl)-rac-glycerol in in 62-65% yield and 2:1 Z:E stereoselectivity; reduction in hexane at 0 OC with slow addition of :triethylaluminum improved the selectivity to > 95% Z. Extension of this method to the preparation of a plasmalogen precursor (1-O-((Z)-1'-hexadecenyl)-2-hexadecanoyl and the first synthesis of a choline derivative of diplasmalogen (1,2-di(O-(Z)-1'-hexadecenyl)-rac-glycerophosphocholine), a major component of rabbit epididymal spermatozoa phospholipid, in moderate chemical yields and excellent Z selectivity is reported.

  DOI：

  10.1021/jo00098a040
• 作为产物：
  描述：

  甘油烯丙基醚 在 咪唑 、 四丁基氟化铵 、 仲丁基锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.42h， 生成 1-O-(1'-hexadecenyl)-rac-glycerol
  参考文献：
  名称：

  Improved Plasmalogen Synthesis Using Organobarium Intermediates

  摘要：

  An improved synthesis of plasmalogen type lipids is described. Transmetalation of lithioalkoxy allyl intermediates with BaI2 and subsequent alkylation with 1-iodoalkanes enables the stereoselective formation of O-(Z)-alkenyl ether as precursors for the synthesis of plasmenyl- and bisplasmenylcholines. This method provides a simple and adaptable approach for the stereocontrolled synthesis of plasmenyl derivatives with variations at the sn-1, sn-2, and sn-3 positions of the glycerol backbone.

  DOI：

  10.1021/jo0705059

文献信息

• [EN] METHODS FOR THE SYNTHESIS OF PLASMALOGENS AND PLASMALOGEN DERIVATIVES, AND THERAPEUTIC USES THEREOF<br/>[FR] PROCÉDÉS POUR LA SYNTHÈSE DE PLASMALOGÈNES ET DE DÉRIVÉS DE PLASMALOGÈNES, ET UTILISATIONS THÉRAPEUTIQUES DE CEUX-CI
  申请人：PHENOMENOME DISCOVERIES INC

  公开号：WO2013071418A1

  公开（公告）日：2013-05-23

  A method for preparing plasmalogens and derivatives thereof represented by Formula B, wherein R1 and R2 are similar or different, derived from fatty acids; R3 is selected from hydrogen and small alkyl groups. The synthetic route involves production of novel cyclic plasmalogen precursors of Formula A and their conversion to plasmalogens and plasmalogen derivatives of Formula B. Also disclosed is the therapeutic use of plasmalogens and derivatives thereof as produced by the synthetic route of the present invention.

  一种制备由化学式B表示的酯烯醇类物质及其衍生物的方法，其中R1和R2为相似或不同，源自脂肪酸；R3从氢和小的烷基组中选择。合成途径涉及制备化学式A的新型环状酯烯醇前体，以及将其转化为化学式B的酯烯醇类物质和其衍生物。还公开了通过本发明的合成途径生产的酯烯醇类物质及其衍生物的治疗用途。
• METHODS FOR THE SYNTHESIS OF PLASMALOGENS AND PLASMALOGEN DERIVATIVES, AND THERAPEUTIC USES THEREOF
  申请人：PHENOMENOME DISCOVERIES INC.

  公开号：US20140296187A1

  公开（公告）日：2014-10-02

  A method for preparing plasmalogens and derivatives thereof represented by Formula B, wherein R1 and R2 are similar or different, derived from fatty acids; R3 is selected from hydrogen and small alkyl groups. The synthetic route involves production of novel cyclic plasmalogen precursors of Formula A and their conversion to plasmalogens and plasmalogen derivatives of Formula B. Also disclosed is the therapeutic use of plasmalogens and derivatives thereof as produced by the synthetic route of the present invention.

  一种制备以公式B表示的鞘磷脂醇和其衍生物的方法，其中R1和R2相似或不同，来自脂肪酸；R3选自氢和小的烷基。合成路线涉及产生新的环状鞘磷脂醇前体物，其公式为A，并将其转化为公式B的鞘磷脂醇和鞘磷脂醇衍生物。本发明还揭示了所述合成路线所产生的鞘磷脂醇和其衍生物的治疗用途。
• METHODS FOR THE SYNTHESIS OF 13C LABELED PLASMALOGEN
  申请人：PHENOMENOME DISCOVERIES INC.

  公开号：US20140323749A1

  公开（公告）日：2014-10-30

  A method for preparing 13 C labeled plasmalogens as represented by Formula B: —The method involves producing a 13 C labeled cyclic plasmalogen precursor of Formula A, and conversion of the precursor to a plasmalogen of Formula B. These plasmalogens may potentially be useful in the determination of both the mechanism of action as well as the fate of plasmalogens in the body.

  一种制备以B式表示的13C标记的鞘磷脂的方法：该方法涉及生产A式的13C标记的环状鞘磷脂前体，并将前体转化为B式的鞘磷脂。这些鞘磷脂可能潜在地有助于确定鞘磷脂在体内的作用机制和命运。
• KNORR, WALTER;SPITELLER, GERHARD, J. CHROMATOGR. BIOMED. APPL., 526,(1990) N, C. 303-318
  作者：KNORR, WALTER、SPITELLER, GERHARD

  DOI：——

  日期：——
• US9006472B2
  申请人：——

  公开号：US9006472B2

  公开（公告）日：2015-04-14