(3R)-3-羟基-十四烷酸乙酯 | 151763-75-6

• 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: (3R)-3-羟基-十四烷酸乙酯
• 英文名称: (R)-3-hydroxytetradecanoic acid ethyl ester
• 英文别名: (R)-ethyl 3-hydroxytetradecanoate；ethyl (3R)-3-hydroxytetradecanoate
• CAS: 151763-75-6
• 化学式: C₁₆H₃₂O₃
• 分子量: 272.428
• InChiKey: GGXXPLYVCUGEOP-OAHLLOKOSA-N

物化性质

• 沸点：
  374.2±15.0 °C(Predicted)
• 密度：
  0.926±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-3-羟基-十四烷酸乙酯 在 偶氮二甲酸二异丙酯 、 氢氟酸 、 二异丁基氢化铝 、 三苯基膦 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 67.0h， 生成 奥利司他
  参考文献：
  名称：

  Total Synthesis and Comparative Analysis of Orlistat, Valilactone, and a Transposed Orlistat Derivative:  Inhibitors of Fatty Acid Synthase

  摘要：

  Concise syntheses of orlistat ( Xenical), a two-carbon transposed orlistat derivative, and valilactone are described that employ the tandem Mukaiyama aldol-lactonization (TMAL) process as a key step. This process allows facile modification of the alpha-side chain. Versatile strategies for modifying the delta-side chain are described, involving cuprate addition and olefin metathesis. Comparative antagonistic activity of these derivatives toward a recombinant form of the thioesterase domain of fatty acid synthase is reported along with comparative activity-based profiling.

  DOI：

  10.1021/ol061651o
• 作为产物：
  描述：

  3-氧代十四酸乙酯 在 Ru(II)-R-BINAP 氢气 作用下， 以 甲醇 为溶剂， 100.0 ℃ 、689.49 kPa 条件下， 反应 12.0h， 以99%的产率得到(3R)-3-羟基-十四烷酸乙酯
  参考文献：
  名称：

  BETA-LACTONE COMPOUNDS

  摘要：

  本发明提供具有一般结构A的化合物，或其药学上可接受的衍生物：其中R是烷基基团，R1包括至少一种从烷基、烯基、芳基、杂环、羟基、酯、酰胺、醛基和卤素组成的基团。

  公开号：

  US20090124681A1

文献信息

• [EN] BIFUNCTIONAL COMPOUND AND ITS USE IN IMMUNOTHERAPY<br/>[FR] COMPOSÉ BIFONCTIONNEL ET SON UTILISATION EN IMMUNOTHÉRAPIE
  申请人：CONSEJO SUPERIOR INVESTIGACION

  公开号：WO2021023512A1

  公开（公告）日：2021-02-11

  The invention relates to a bifunctional compound that is, on one side, an agonist of the TLR4 and, on the other side, an important inhibitor of the PSMA. Said compound is useful in immunotherapy for the treatment and/or prevention of prostate cancer. Therefore, the invention also relates to the use of the compound and to the pharmaceutical composition comprising it.

  这项发明涉及一种双功能化合物，一方面是TLR4的激动剂，另一方面是PSMA的重要抑制剂。该化合物在免疫疗法中用于治疗和/或预防前列腺癌。因此，该发明还涉及该化合物的使用以及包含该化合物的药物组合物。
• SYNTHETIC DERIVATIVES OF MPL AND USES THEREOF
  申请人：VARIATION BIOTECHNOLOGIES INC.

  公开号：US20140328876A1

  公开（公告）日：2014-11-06

  In one aspect, the present disclosure provides compounds of formulae (I) and (II). In another aspect, a compound of formula (I) or (II) is formulated into compositions with an antigen, optionally with a vesicle. In some embodiments, compositions are administered intramuscularly.

  在一个方面，本公开提供了式(I)和(II)的化合物。在另一个方面，将式(I)或(II)的化合物与抗原配制成组合物，可选地与囊泡一起。在一些实施方式中，这些组合物是肌肉注射给药的。
• Synthesis of Novel β-Lactone Inhibitors of Fatty Acid Synthase
  作者：Robyn D. Richardson、Gil Ma、Yatsandra Oyola、Manuel Zancanella、Lynn M. Knowles、Piotr Cieplak、Daniel Romo、Jeffrey W. Smith

  DOI：10.1021/jm800321h

  日期：2008.9.11

  Fatty acid synthase (FAS) is necessary for growth and survival of tumor cells and is a promising drug target for oncology. Here, we report oil the syntheses and activity of novel inhibitors of the thioesterase domain of FAS. Using the structure of orlistat as a starting point, which contains a beta-lactone as the central pharmacophore, 28 novel congeners were synthesized and examined. Structural features such as the length of the alpha- and beta-alkyl chains, their chemical composition, and arnino ester substitutions were altered and tile resulting compounds explored for inhibitory activity toward the thioesterase domain of FAS. Nineteen congeners show improved potency for FAS in biochemical assays relative to orlistat. Three of that subset, including the natural product valilactone, also display all increased potency in inducing tumor cell death and improved solubility compared to orlistat. These findings Support the idea that all orlistat congener can be optimized for use in a preclinical drug design and for clinical drug development.
• An efficient synthesis of (R)-3-hydroxytetradecanoic acid
  作者：Guangfei Huang、Rawle I. Hollingsworth

  DOI：10.1016/s0957-4166(98)00441-8

  日期：1998.12

  A short, efficient synthesis of (R)-3-hydroxytetradecanoic acid, a key component of bacterial endotoxins, using (R)-oxirane acetic acid ethyl ester as the source of chirality is described. The method is general and can be used in the preparation of other chiral 3-hydroxy acids. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Highly Enantioselective Hydrogenation of β‐Alkyl and β‐(ω‐Chloroalkyl) Substituted β‐Keto Esters
  作者：Iyad Karamé、Esen Bellur、Sven Rotzoll、Peter Langer、Christine Fischer、Jens Holz、Armin Börner

  DOI：10.1080/00397910701196538

  日期：2007.4.1

  Highly enantioselective hydrogenation of beta-alkyl and beta-(omega-chloroalkyl) substituted beta-keto esters was achieved with Ru catalysts based on chiral diphosphinesin EtOH at 50 degrees C under 50-bar initial hydrogen pressure, affording the corresponding beta-hydroxy esters in > 98% ee.