methyl (E)-tetradec-2-enoate | 14812-04-5

• 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 (E)-tetradec-2-enoate
• 英文别名: Methyl tetradecenoate
• CAS: 14812-04-5
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: CKTWGIPZKUEHIY-BUHFOSPRSA-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 (E)-tetradec-2-enoate 在 lithium hydroxide monohydrate 、 盐酸 作用下， 以 1,4-二氧六环 、 水 、 二氯甲烷 为溶剂， 反应 48.0h， 以90%的产率得到(E)-tetradec-2-enoic acid
  参考文献：
  名称：

  trans-Tetradec-2-enoic Acid in Impatiens glandulifera

  摘要：

  Purification of the hydrophobic extracts of the flowers and seed pods of Impatiens glandulifera(Himilayan balsam) yielded 2-methoxy-[1,4]-naphthoquinone 1, 1-hydroxyeicosan-3-one 16, and an unusual unsaturated fatty acid, trans-tetradec-2-enoic acid 6. Mass spectrometry and nuclear magnetic resonance spectroscopy indicated that the latter compound (6) was isolated as a mixture with linolenic acid 8 and saturated acids 7, 9, and 10 (chain lengths C-16, 18, and 20). Its structure was subsequently proven by independent chemical synthesis. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.635395
• 作为产物：
  描述：

  (E)-tetradec-2-enoic acid 生成 methyl (E)-tetradec-2-enoate
  参考文献：
  名称：

  ROHWEDDER, WILLIAM K.;DUVAL, SANDRA M.;WOLF, DARHAL J.;EMKEN, EDWARD A., LIPIDS., 25,(1990) N, C. 401-405

  摘要：

  DOI：

文献信息

• Ir-Catalyzed Remote Functionalization by the Combination of Deconjugative Chain-Walking and C–H Activation Using a Transient Directing Group
  作者：King Hung Nigel Tang、Kanako Uchida、Kazuki Nishihara、Mamoru Ito、Takanori Shibata

  DOI：10.1021/acs.orglett.1c04321

  日期：2022.2.18

  N-benzylideneanilines with functionalized alkenes such as α,β-unsaturated esters gave ortho-substituted benzaldehyde derivatives with a functional group at the remote position after acidic treatment. The present transformation involves deconjugative long-range isomerization (chain-walking) up to 11 times and C–H activation using an imino group as a transient directing group.

  在 Ir 催化下，N-亚苄基苯胺与功能化烯烃（如 α,β-不饱和酯）反应得到邻位取代的苯甲醛衍生物，酸处理后在远端位置具有官能团。目前的转化涉及高达 11 次的解共轭远程异构化（链行走）和使用亚氨基作为瞬态导向基团的 C-H 活化。
• Aciculitin D, a cytotoxic heterodetic cyclic peptide from a Poecillastra sp. marine sponge
  作者：Kenji Sugawara、Daichi Kanki、Ryuichi Watanabe、Ryoji Matsushima、Yuji Ise、Hisayoshi Yokose、Yasuhiro Morii、Nobuhiro Yamawaki、Akihiro Ninomiya、Shigeru Okada、Shigeki Matsunaga

  DOI：10.1016/j.tet.2022.132859

  日期：2022.7

  A new cyclic lipopeptide aciculitin D (1) was isolated from a Poecillastra sp. marine sponge collected in the deep-sea. The structure of aciculitin D (1) was elucidated by spectroscopic analyses and chemical degradation. With regard to amino acid sequence, aciculitin D is different from aciulitin B in one residue substitution of L-Gln for L-Thr. However, absolute configurations of some of the residues

  从Poecillastra sp.中分离出一种新的环状脂肽 aciculitin D ( 1 )。在深海中收集的海绵。通过光谱分析和化学降解阐明了aciculitin D( 1 )的结构。就氨基酸序列而言，aciulitin D与aciulitin B的不同之处在于L-Gln对L-Thr的一个残基取代。然而，两种化合物之间某些残基的绝对构型不同。Aciculitin D ( 1 ) 对 HeLa 和 HCT-116 细胞具有细胞毒性，IC 50值分别为 4.5 μM 和 1.4 μM。
• Enders, Dieter; Wahl, Heiner; Bettray, Wolfgang, Angewandte Chemie, 1995, vol. 107, # 4, p. 527 - 529
  作者：Enders, Dieter、Wahl, Heiner、Bettray, Wolfgang

  DOI：——

  日期：——
• Mahipal Reddy; Raj Gopal; Jayathirtha Rao, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 4, p. 312 - 317
  作者：Mahipal Reddy、Raj Gopal、Jayathirtha Rao

  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.