trans-1-phenyl-1-decen-3-one | 95123-16-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: trans-1-phenyl-1-decen-3-one
• 英文别名: (1E)-phenyldec-1-en-3-one；(E)-1-phenyldec-1-en-3-one
• CAS: 95123-16-3
• 化学式: C₁₆H₂₂O
• 分子量: 230.35
• InChiKey: YWKNPRIZEDLBKJ-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-1-phenyl-1-decen-3-one 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 3.0h， 以90%的产率得到(E)-1-phenyl-1-decen-3-ol
  参考文献：
  名称：

  Evaluation of the antitrypanosoma activity and SAR study of novel LINS03 derivatives

  摘要：

  Chagas' disease is a parasitic infection caused by Trypanosoma cruzi that is still treated by old and toxic drugs. In the search for novel alternatives, natural sources are an important source for new drug prototypes against T. cruzi to further structural exploitation. A set of natural-based compounds (LINS03) was designed, showing promising antitrypanosoma activity and low cytotoxicity to host cells. In this paper, nine novel LINS03 derivatives were evaluated against T. cruzi trypomastigotes and amastigotes. The selectivity was assessed through cytotoxicity assays using NCTC mammalian cells and calculating the CC50/IC50 ratio. The results showed that compounds 2d and 4c are noteworthy, due their high activity against amastigotes (IC50 13.9 and 5.8 mu M) and low cytotoxicity (CC50 107.7 mu M and > 200 mu M, respectively). These compounds did not showed alteration on plasma membrane permeability in a Sytox green model. SAR analysis suggested an ideal balance between hydrosolubility and lipophilicity is necessary to improve the activity, and that insertion of a meta-substituent is detrimental to the activity of the amine derivatives but not to the neutral derivatives, suggesting different mechanisms of actions. The results presented herein are valuable for designing novel compounds with improved activity and selectivity to be applied in future studies.

  DOI：

  10.1016/j.bioorg.2019.102996
• 作为产物：
  描述：

  2-壬酮 、 苯甲醛 在 sodium hydroxide 作用下， 以 neat (no solvent) 为溶剂， 反应 0.25h， 以90%的产率得到trans-1-phenyl-1-decen-3-one
  参考文献：
  名称：

  Evaluation of the antitrypanosoma activity and SAR study of novel LINS03 derivatives

  摘要：

  Chagas' disease is a parasitic infection caused by Trypanosoma cruzi that is still treated by old and toxic drugs. In the search for novel alternatives, natural sources are an important source for new drug prototypes against T. cruzi to further structural exploitation. A set of natural-based compounds (LINS03) was designed, showing promising antitrypanosoma activity and low cytotoxicity to host cells. In this paper, nine novel LINS03 derivatives were evaluated against T. cruzi trypomastigotes and amastigotes. The selectivity was assessed through cytotoxicity assays using NCTC mammalian cells and calculating the CC50/IC50 ratio. The results showed that compounds 2d and 4c are noteworthy, due their high activity against amastigotes (IC50 13.9 and 5.8 mu M) and low cytotoxicity (CC50 107.7 mu M and > 200 mu M, respectively). These compounds did not showed alteration on plasma membrane permeability in a Sytox green model. SAR analysis suggested an ideal balance between hydrosolubility and lipophilicity is necessary to improve the activity, and that insertion of a meta-substituent is detrimental to the activity of the amine derivatives but not to the neutral derivatives, suggesting different mechanisms of actions. The results presented herein are valuable for designing novel compounds with improved activity and selectivity to be applied in future studies.

  DOI：

  10.1016/j.bioorg.2019.102996

文献信息

• Smoking compositions containing an alpha-alkylcinnamaldehyde-release additive
  申请人：Philip Morris Products Inc.

  公开号：EP0578421A1

  公开（公告）日：1994-01-12

  This invention provides smoking compositions which contain a novel β-hydroxy-carboxylate flavorant-release additive. Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as calcium bis(2,2-diethyl-3-hydroxy-4-phenylmethylenedecanoate) pyrolyzes and releases α-hexylcinnamaldehyde as a volatile flavorant component of the cigarette smoke.

  本发明提供了含有新型β-羟基羧酸盐香料释放添加剂的烟用组合物。 在卷烟吸食条件下，双（2,2-二乙基-3-羟基-4-苯基亚甲基癸酸钙）等可燃填料和/或包装纸添加剂会热解并释放出α-己基肉桂醛，作为卷烟烟气中的挥发性香料成分。
• Metallic nickel-mediated synthesis of ketones by the reaction of benzylic, allylic, vinylic, and pentafluorophenyl halides with acid halides
  作者：Shinichi Inaba、Reuben D. Rieke

  DOI：10.1021/jo00209a006

  日期：1985.5
• Acylation of Alkenes with the Aid of AlCl₃ and 2,6-Dibromopyridine
  作者：Shinya Tanaka、Tsukasa Kunisawa、Yuji Yoshii、Tetsutaro Hattori

  DOI：10.1021/acs.orglett.9b02688

  日期：2019.11.1

  Friedel-Crafts-type acylation of alkenes with acyl chlorides has been successfully conducted with a wide substrate scope by the combined use of AlCl3 and 2,6-dibromopyridine. Trisubstituted alkenes afford allylketones or vinylketones depending on the presence or absence of hydrogen atom(s) at the beta-position to the acylation site, while monosubstituted alkenes exclusively afford vinylketones.
• INABA, SHIN-ICHI;RIEKE, R. D., J. ORG. CHEM., 1985, 50, N 9, 1373-1381
  作者：INABA, SHIN-ICHI、RIEKE, R. D.

  DOI：——

  日期：——
• SYTIN V. N.; TISHCHENKO I. G., BECTH. BELORUS. YH-TA,(1986) N 3, 22-26
  作者：SYTIN V. N.、 TISHCHENKO I. G.

  DOI：——

  日期：——