methyl tetradec-2-enoate | 22104-73-0

• 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 tetradec-2-enoate
• 英文别名: tetradec-2-enoic acid methyl ester；Tetradec-2-ensaeure-methylester；2-Tetradecensaeuremethylester；2-Tetradecenoic acid methylester
• CAS: 22104-73-0
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: CKTWGIPZKUEHIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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 tetradec-2-enoate 在 甲醇 、 lithium hydroxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (E)-tetradec-2-enoyl chloride
  参考文献：
  名称：

  Aciculitins A−C:  Cytotoxic and Antifungal Cyclic Peptides from the Lithistid Sponge Aciculites orientalis

  摘要：

  The lithistid sponge Aciculites orientalis contains three cyclic peptides, aciculitins A-C (1-3), that are identical except for homologous lipid residues. The structure of the major peptide, aciculitin B (2), was elucidated by interpretation of spectroscopic data. The aciculitins consist of a bicyclic peptide that contains an unusual histidino-tyrosine bridge. Attached to the bicyclic peptide are C-13-C-15 2,3-dihydroxy-4,6-dienoic acids bearing D-lyxose at the 3-position. The structures of aciculitamides A (4) and B (5), which are artifacts obtained earlier from this sponge, are also presented. The aciculitins 1--3 inhibited the growth of Candida albicans and were cytotoxic toward the HCT-116 cell line.

  DOI：

  10.1021/ja953628w
• 作为产物：
  描述：

  2-Acetoxy-tetradecansaeure-methylester 生成 methyl tetradec-2-enoate
  参考文献：
  名称：

  Ogibin,J.N.; Nikischin,G.J., Angewandte Chemie, 1964, vol. 76, p. 713

  摘要：

  DOI：

文献信息

• A new method for carbon-carbon double bond formation promoted by tri-n-butylphosphine and zinc
  作者：Yanchang Shen、Yuankang Xin、Jianhua Zhao

  DOI：10.1016/s0040-4039(00)82281-9

  日期：——

  A new method for the carbon-carbon double bond formation by the reaction of aldehydes with methyl bromoacetate promoted by tri-n-butylphosphine and zinc has been described.

  已经描述了通过醛与由三正丁基膦和锌促进的溴乙酸甲酯反应形成碳-碳双键的新方法。
• Synthesis and Antifungal Activity of Rhodopeptin Analogues. 1. Modification of the East and South Amino Acid Moieties
  作者：Haruko C. Kawato、Kiyoshi Nakayama、Hiroaki Inagaki、Ryohei Nakajima、Akihiro Kitamura、Kazuhiko Someya、Toshiharu Ohta

  DOI：10.1021/ol005631c

  日期：2000.4.1

  [GRAPHICS]Structure-activity relationships of the east and south amino acid modified analogues of rhodopeptins, novel antifungal cyclic tetrapeptides isolated from Rhodococcus species Mer-N1033, have been investigated. It was observed that a basic amino acid moiety (lysine or ornithine) as the east amino acid and a hydrophobic and bulky neutral amino acid (i.e., gamma-methylleucine) as the south amino acid were indispensable structure motifs for antifungal activity of rhodopeptin analogues.
• Bruce, Ian; Spencer, Robert; Tyman, John, Journal of Chemical Research, Miniprint, 1992, # 7, p. 1773 - 1795
  作者：Bruce, Ian、Spencer, Robert、Tyman, John

  DOI：——

  日期：——
• Ogibin,J.N.; Nikischin,G.J., Angewandte Chemie, 1964, vol. 76, p. 713
  作者：Ogibin,J.N.、Nikischin,G.J.

  DOI：——

  日期：——
• Aciculitins A−C:  Cytotoxic and Antifungal Cyclic Peptides from the Lithistid Sponge <i>Aciculites </i><i>orientalis</i>
  作者：Carole A. Bewley、Haiyin He、David H. Williams、D. John Faulkner

  DOI：10.1021/ja953628w

  日期：1996.1.1

  The lithistid sponge Aciculites orientalis contains three cyclic peptides, aciculitins A-C (1-3), that are identical except for homologous lipid residues. The structure of the major peptide, aciculitin B (2), was elucidated by interpretation of spectroscopic data. The aciculitins consist of a bicyclic peptide that contains an unusual histidino-tyrosine bridge. Attached to the bicyclic peptide are C-13-C-15 2,3-dihydroxy-4,6-dienoic acids bearing D-lyxose at the 3-position. The structures of aciculitamides A (4) and B (5), which are artifacts obtained earlier from this sponge, are also presented. The aciculitins 1--3 inhibited the growth of Candida albicans and were cytotoxic toward the HCT-116 cell line.