16-氟十六烷酸 | 3109-58-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 16-氟十六烷酸
• 中文别名: 2-苯甲基-4,5-二氢-1H-咪唑5-乙基-5-苯基-六氢嘧啶-2,4,6-三酮N-甲基-N-苯乙基-2-苯基-乙胺
• 英文名称: 16-fluorohexadecanoic acid
• 英文别名: 16-fluoropalmitic acid；16-Fluor-hexadecansaeure；16-Fluor-palmitinsaeure
• CAS: 3109-58-8
• 化学式: C₁₆H₃₁FO₂
• 分子量: 274.419
• InChiKey: PNNLLDRVJFDXNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2915900090

反应信息

• 作为反应物：
  描述：

  16-氟十六烷酸 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 6-<4-deoxy-4-(16-fluorohexadecanoyl)glycylamino-L-glycero-β-L-manno-heptapyranosylamino>-9H-purine
  参考文献：
  名称：

  Structure-antitumor Activity Relationship of Semi-synthetic Spicamycin Derivatives.

  摘要：

  新合成了一系列在分子脂肪酸部分进行了修饰的斯匹卡霉素衍生物，并研究了它们的构效关系。通过对脂肪酸部分进行修饰，将其转化为十四碳二烯酸或十二碳二烯酸类似物，这些衍生物对COL-1人结肠癌异种移植模型的抗肿瘤活性显著优于SPM VIII。

  DOI：

  10.7164/antibiotics.48.1467
• 作为产物：
  描述：

  16-羟基棕榈酸 在 N,N-二乙基(2-氯-1,1,2-三氟乙基)胺 作用下， 生成 16-氟十六烷酸
  参考文献：
  名称：

  Cross,B.E.; Hendley,P., Journal of the Chemical Society. Perkin transactions I, 1975, p. 2523 - 2525

  摘要：

  DOI：

文献信息

• Spicamycin derivatives and their use as anticancer agents
  申请人：Kirin Beer Kabushiki Kaisha

  公开号：US05461036A1

  公开（公告）日：1995-10-24

  Spicamycin derivative represented by the formula (I) or a salt thereof: ##STR1## wherein R represents specific diverse substituents, for example, a linear alkadienyl having from 11 to 13 carbon atoms, and R.sub.1 and R.sub.2 respectively represent H or OH. Examples of specific compounds are 6-[4'-N-(N'-trans,trans 2,4-tridecadienoylglycyl)spicaminyl-amino]purine, and 6-[4'-N-(N'-trans,trans-2,4 dodecadienyoly glycyl) spicaminyl-amino]purine. Comopunds according to this invention are useful as a pharmaceutical for inhibition of a tumor, for example, human colon cancer.

  公式（I）代表的Spicamycin衍生物或其盐：其中R代表特定的不同取代基，例如，具有11至13个碳原子的直链烯基，而R.sub.1和R.sub.2分别代表H或OH。具体化合物的示例是6-[4'-N-(N'-反式、反式2,4-十三碳二烯酰基甘氨酸)孢菌素基氨基]嘌呤，以及6-[4'-N-(N'-反式、反式-2,4-十二碳烯基甘氨酸)孢菌素基氨基]嘌呤。根据本发明的化合物可用作抑制肿瘤的药物，例如，人类结肠癌。
• [EN] NOVEL DERIVATIVES OF PALIPERIDONE AND PROCESS FOR THE PREPARATION THEREOF<br/>[FR] NOUVEAUX DÉRIVÉS DE PALIPÉRIDONE ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：ZENVISION PHARMA LLP

  公开号：WO2019162746A1

  公开（公告）日：2019-08-29

  The present disclosure relates to novel hydroxyl or halogen substituted derivatives of C11- C22 alkanoic acid ester of Paliperidone compound of formula (formula II) and process for preparing the same. The said compounds used in pharmaceutical composition for the treatment of schizophrenia and schizoaffective disorder, wherein, R= C10-C21 alkyl substituted by hydroxy or halogen.

  本公开涉及Paliperidone化合物的C11-C22烷基羟基或卤素取代衍生物（式II的化合物）的新型衍生物，以及制备这些衍生物的方法。所述化合物用于治疗精神分裂症和分裂情感障碍的药物组合物中，其中R=C10-C21烷基，其被羟基或卤素取代。
• Derivatives of paliperidone and process for the preparation thereof
  申请人：Zenvision Pharma LLP

  公开号：US11377445B2

  公开（公告）日：2022-07-05

  The present disclosure relates to novel hydroxyl or halogen substituted derivatives of C11-C22 alkanoic acid ester of Paliperidone compound of formula (formula II) and process for preparing the same. The said compounds used in pharmaceutical composition for the treatment of schizophrenia and schizoaffective disorder, wherein, R═C10-C21 alkyl substituted by hydroxy or halogen.

  本公开涉及式（式 II）化合物的 C11-C22 烷酸帕潘立酮酯的羟基或卤素取代的新型衍生物及其制备工艺。所述化合物用于治疗精神分裂症和分裂情感障碍的药物组合物中，其中，R═C10-C21 烷基被羟基或卤素取代。
• <b>Toxic Fluorine Compounds. XVIII.¹ The Synthesis of the Toxic Principle of <b><i>Dichapetalum toxicarium</i></b> (18-Fluoro-<b><i>cis</i></b>-9-octadecenoic Acid) and Related ω-Fluoro Unsaturated Acids</b>^2,3
  作者：R. E. A. Dear、F. L. M. Pattison

  DOI：10.1021/ja00888a032

  日期：1963.3
• [F-18]labeling of 1,2-diacylglycerols
  作者：Toshihiro Takahashi、Tatsuo Ido、Shinji Nagata、Ren Iwata

  DOI：10.1002/1099-1344(200008)43:9<943::aid-jlcr379>3.0.co;2-v

  日期：2000.8

  We have developed two kinds of [F-18]labeled 1,2-diacylglycerols (1,2-DAGs) such as 1-(omega-[F-18]fluoroacyl)-2-acylglycerols (1*,2-[F-18]FDAGs) and 2-(omega-[F-18]fluoroacyl)-1-acylglycerols (1,2*-[F-18]FDAGs) for imaging receptor-mediated phosphatidyl-inositol (PI) turnover responses by positron emission tomography (PET). The 1*,2-[F-18]FDAGs were synthesized by the reaction of 2-monoacyl glycerols with omega-[F-18]fluoroacyl chlorides (method A) and 1-(16-[F-18]fluoro palmitoyl)-2-palmitoylglycerol (1*,2-[F-18]FDAG(C16,C16)) and 1-(8-[F-18]fluoro octanoyl)-2-palmitoylglycerol (1*,2-[F-18]FDAG(C8,C16)) were synthesized using method A. However, during the synthesis of 1,2*-[F-18]FDAGs, we adopted the hydrogenolysis to remove a benzyl group from 3-O-benzyl-2-(omega-[F-18]fluoroacyl)-1-acylglycerol, which was synthesized by the nucleophilic exchange reaction of 3-O-benzyl-2-(omega-bromoacyl)-1-acylglycerol with [F-18]F- (method B) and 2-(16-[F-18]fluoropalmitoyl)-1-palmitoylglycerol (1,2*-[F-18]FDAG(C16,C16)) and [F-18]fluorooctanoyl)-1-palmitoylglycerol (1,2*-[F-18]FDAG(C16,C8)) were produced using method B. The purified 1*,2-[F-18]FDAGs were obtained in radiochemical yields of 8-35 % (based on [F-18]F-) with radiochemical purities of > 97 % and the purified 1,2*-[F-18]FDAGs were in radiochemical yields of 5-15 % with radiochemical purities of > 95 %. The total synthesis time from the start of the reactive [F-18]F- production, including HPLC purification, was 100 - 135 min (method A) and 115 - 175 min (method B), respectively. It has already been used for more than 100 preparations of 1*,2-[F-18]FDAG(C16,C16), 1*,2-[F-18]FDAG(C8, C16), and 1,2*-[F-18]FDAG(C16,C16), 1,2*-[F-18]FDAG(C16,C8) for animal studies.