12-methoxydodecanoyl chloride | 187885-81-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 12-methoxydodecanoyl chloride
• CAS: 187885-81-0
• 化学式: C₁₃H₂₅ClO₂
• 分子量: 248.793
• InChiKey: VSZWOYIFKNBMSW-UHFFFAOYSA-N

物化性质

• 沸点：
  303.6±15.0 °C(Predicted)
• 密度：
  0.964±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  12-methoxydodecanoyl chloride 在 palladium on activated charcoal 、 O-trimethylsilyl quinine 氢气 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 (3R,4S)-4-(10-methoxydecyl)-3-(9-methoxynonyl)oxetan-2-one
  参考文献：
  名称：

  Practical, Catalytic, Asymmetric Synthesis of β-Lactones via a Sequential Ketene Dimerization/Hydrogenation Process:  Inhibitors of the Thioesterase Domain of Fatty Acid Synthase

  摘要：

  The recent finding that the FDA-approved antiobesity agent orlistat ( tetrahydrolipstatin, Xenical) is a potent inhibitor of the thioesterase domain of fatty acid synthase (FAS) led us to develop a concise and practical asymmetric route to pseudosymmetric 3,4-dialkyl-cis-beta-lactones. The well-documented upregulation of FAS in cancer cells makes this enzyme complex an interesting therapeutic target for cancer. The described route to 3,4-dialkyl-beta-lactones is based on a two-step process involving Calter's catalytic, asymmetric ketene dimerization of acid chlorides followed by a facial-selective hydrogenation leading to cis-substituted-beta-lactones. Importantly, the ketene dimer intermediates were found to be stable to flash chromatography, enabling opportunities for subsequent transformations of these optically active, reactive intermediates. Subsequent alpha-epimerization and alpha-alkylation or acylation led to trans-beta-lactones and beta-lactones bearing alpha-quaternary carbons, respectively. Several of the ketene dimers and beta-lactones displayed antagonistic activity (apparent K-i in the low micromolar range) in competition with a fluorogenic substrate toward a recombinant form of the thioesterase domain of fatty acid synthase. The best antagonist, a simple phenyl-substituted cis-beta-lactone 3d, displayed an apparent K-i (2.5 +/- 0.5 mu M) of only similar to 10-fold lower than that of orlistat (0.28 +/- 0.06 mu M). In addition, mechanistic studies of the ketene dimerization process by ReactionView infrared spectroscopy support previous findings that ketene formation is rate determining.

  DOI：

  10.1021/jo060392d
• 作为产物：
  描述：

  12-甲氧基十二酸 在 草酰氯 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 12-methoxydodecanoyl chloride
  参考文献：
  名称：

  3'-氟-2'，3'-二脱氧胸苷（FLT）的5'-O-肉豆蔻酰基类似物衍生物的合成，体外抗HIV活性和生物学稳定性，它们是FLT的潜在双功能前药。

  摘要：

  一组FLT的5'-O-肉豆蔻酰基类似物衍生物（2）被评估为潜在的抗HIV药物，被设计用作FLT的前药。3'-氟-2'，3'-二脱氧-5'-O-（12-甲氧基十二烷酰基）胸苷（4）（EC50 = 3.8 nM）和3'-氟-2'，3'-二脱氧-5'- O-（12-叠氮基十二烷酰基）胸苷（8）（EC50 = 2.8 nM）是最有效的抗HIV-1药物。5'-O-FLT酯的Log P和HPLC Log保留时间之间存在线性关系。猪肝酯酶，大鼠血浆和大鼠脑匀浆中酯类（3-8）中的体外酶促水解半衰期（t1 / 2）较长，对于3'-氟-2'，3'-二脱氧-5'-O-（肉豆蔻酰基）胸苷（7），t1 / 2值分别为20.3、4.6和17.5分钟。

  DOI：

  10.1080/07328319808004216

文献信息

• Fatty acid analogs and prodrugs
  申请人：G. D. Searle & Co.

  公开号：US05859052A1

  公开（公告）日：1999-01-12

  Novel derivatives of fatty acid analogs that have from one to three heteroatoms in the fatty acid moiety which can be oxygen, sulfur or nitrogen, are disclosed in which the carboxy-terminus has been modified to form various amides, esters, ketones, alcohols, alcohol esters and nitrites thereof. These compounds are useful as substrates for N-myristoyltransferase (NMT) and/or its acyl coenzyme, and as anti-viral and anti-fungal agents or pro-drugs of such agents. Illustrative of the disclosed compounds are fatty acid amino acid analogs of the structure ##STR1## in which x is the ethyl or t-butyl ester of an amino acid such as Gly, L-Ala, L-Ile, L-Phe, L-Trp, L-Thr or an amide such as NHCH.sub.2 C.sub.6 H.sub.5 or NH(CH.sub.2).sub.2 C.sub.6 H.sub.5.

  脂肪酸类似物的新衍生物揭示了脂肪酸部分中含有一到三个杂原子（氧、硫或氮），其中羧基末端已经被改性以形成各种酰胺、酯、酮、醇、醇酯和亚硝酸盐。这些化合物可用作N-肌醇转移酶（NMT）及/或其酰辅酶的底物，以及抗病毒和抗真菌剂或这些剂的前药。所述化合物的示例是脂肪酸氨基酸类似物，其结构为##STR1## 其中x是氨基酸（如甘氨酸、L-丙氨酸、L-异亮氨酸、L-苯丙氨酸、L-色氨酸、L-苏氨酸）的乙酯或叔丁基酯，或者是NHCH.sub.2 C.sub.6 H.sub.5或NH(CH.sub.2).sub.2 C.sub.6 H.sub.5等酰胺。
• Synthesis and properties of 11-(3,5-Di-tert-butyl-2-hydroxyphenylcarbamoyl)undecanoic acid, a new amphiphilic antioxidant
  作者：Vladimir I Lodyato、Irina L Yurkova、Viktor L Sorokin、Oleg I Shadyro、Vladimir I Dolgopalets、Mikhail A Kisel

  DOI：10.1016/s0960-894x(03)00041-6

  日期：2003.3

  Based on the membrane addressing concept, designing and synthesis of 11-(3,5-di-tert-butyl-2-hydroxyphenylcarbamoyl)undecanoic acid have been carried out. Antioxidant properties of the prepared compound were investigated in comparison with its non-amphiphilic analogues. (C) 2003 Elsevier Science Ltd. All rights reserved.
• US5599947A
  申请人：——

  公开号：US5599947A

  公开（公告）日：1997-02-04
• US5670650A
  申请人：——

  公开号：US5670650A

  公开（公告）日：1997-09-23
• US5672769A
  申请人：——

  公开号：US5672769A

  公开（公告）日：1997-09-30