ethyl 7-methyl-3-(((trifluoromethyl)sulfonyl)oxy)-octa-2(Z),6-dienoate | 463964-46-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: ethyl 7-methyl-3-(((trifluoromethyl)sulfonyl)oxy)-octa-2(Z),6-dienoate
• 英文别名: ethyl (Z)-7-methyl-3-(trifluoromethanesulfonyloxy)octa-2,6-dienoate；ethyl (2Z)-7-methyl-3-(trifluoromethylsulfonyloxy)-2,6-octadienoate；ethyl (2Z)-7-methyl-3-(trifluoromethylsulfonyloxy)octa-2,6-dienoate
• CAS: 463964-46-7
• 化学式: C₁₂H₁₇F₃O₅S
• 分子量: 330.325
• InChiKey: MYRNKXPHVJWUHM-NTMALXAHSA-N

物化性质

• 沸点：
  368.8±42.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 7-methyl-3-(((trifluoromethyl)sulfonyl)oxy)-octa-2(Z),6-dienoate 在 二(氰基苯)二氯化钯 copper(l) iodide 、 正丁基锂 、 四溴化碳 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 二氯甲烷 、 环己烷 、 甲苯 为溶剂， 反应 21.0h， 生成 ethyl 7-allyl-11-methyl-3-oxo-dodeca-6(Z),10-dienoate
  参考文献：
  名称：

  Synthesis of 7-Substituted Farnesyl Diphosphate Analogues

  摘要：

  [GRAPHICS]Six farnesyl diphosphate analogues modified in the central isoprene unit have been prepared via our stereoselective vinyl triflate-mediated route to isoprenoids. The 7-allyl compound 6 is a modest inhibitor of mammalian protein-farnesyl transferase, but surprisingly the other five analogues are effective alternative substrates for this enzyme.

  DOI：

  10.1021/ol026176i
• 作为产物：
  描述：

  ethyl acetoacetate sodium salt 在 正丁基锂 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 环己烷 、 甲苯 为溶剂， 反应 1.0h， 生成 ethyl 7-methyl-3-(((trifluoromethyl)sulfonyl)oxy)-octa-2(Z),6-dienoate
  参考文献：
  名称：

  Synthesis of 7-Substituted Farnesyl Diphosphate Analogues

  摘要：

  [GRAPHICS]Six farnesyl diphosphate analogues modified in the central isoprene unit have been prepared via our stereoselective vinyl triflate-mediated route to isoprenoids. The 7-allyl compound 6 is a modest inhibitor of mammalian protein-farnesyl transferase, but surprisingly the other five analogues are effective alternative substrates for this enzyme.

  DOI：

  10.1021/ol026176i

文献信息

• Synthesis of Substituted Benzenes and Phenols by Ring-Closing Olefin Metathesis
  作者：Kazuhiro Yoshida、Hidetoshi Takahashi、Tsuneo Imamoto

  DOI：10.1002/chem.200800484

  日期：2008.9.19

  New synthetic approaches to substituted aromatic compounds are reported. Ring-closing olefin metathesis (RCM)/dehydration and RCM/tautomerization are the key processes in the synthesis of substituted benzenes 3 and phenols 6, respectively. Readily accessible 1,5,7-trien-4-ols 7, which are the precursors of benzenes, were prepared from beta-halo-alpha,beta-unsaturated aldehydes 11 or beta-halo-alpha

  报道了取代芳族化合物的新合成方法。闭环烯烃复分解（RCM）/脱水和RCM /互变异构是分别合成取代苯3和苯酚6的关键过程。易得的1,5,7-trien-4-ols 7是苯的前体，它是利用β-卤代α，β-不饱和醛11或β-卤代α，β-不饱和酯19通过利用可靠的转化方法，其中与乙烯基金属试剂12的交叉偶联和与烯丙基金属试剂13的烯丙基化被用作碳-碳键形成反应。RCM为7，然后脱水，得到了各种各样的取代苯3。此外，通过氧化7制备的1,5,7-三烯-4-酮9的RCM，自动提供了各种取代的苯酚6。互变异构化。
• A Versatile and Highly Stereoselective Access to Vinyl Triflates Derived from 1,3-Dicarbonyl and Related Compounds
  作者：Simon Specklin、Philippe Bertus、Jean-Marc Weibel、Patrick Pale

  DOI：10.1021/jo8015049

  日期：2008.10.3

  trialkylamines or DBU followed by trapping with triflic anhydride probably accounted for such high selectivity, achieved even at 0 degrees C. This method offers the first direct route to vinyl triflates from beta-ketoamides, beta-ketophosphonates and beta-ketosulfones.

  1,3-二羰基衍生物，例如1,3-二酮，β-酮醛，β-酮酸酯，β-酮酰胺，β-酮膦酸酯和β-酮砜被高效地转化为相应的具有高立体选择性的Z乙烯基三氟甲磺酸酯。在二氯甲烷中用三氟甲磺酸锂进行预配位，然后用温和的碱（例如三烷基胺或DBU）进行烯化，然后用三氟甲磺酸酐进行捕获，可能导致如此高的选择性，即使在0摄氏度下也是如此。这种方法为从β-酮酰胺制得三氟甲磺酸三氟甲磺酸酯提供了第一条直接途径，β-酮膦酸酯和β-酮砜。
• Compounds and methods for use in treating neoplasia and cancer based upon inhibitors of isoprenylcysteine methyltransferase
  申请人：Gibbs A. Richard

  公开号：US20070004803A1

  公开（公告）日：2007-01-04

  The present invention relates to a novel method for the treatment of neoplasia, including cancer and other diseases and conditions in humans and mammals. More particularly, in preferred aspects, the present invention provides a method for the use of prenylcysteine analogs for the treatment of neoplasia, hyperproliferative cell growth including psoriasis, restenosis following cardiovascular surgery, hyperplasia, including renal hyperplasia, chronic inflammatory diseases including rheumatoid and osteoarthritis, among others.

  本发明涉及一种新的治疗肿瘤的方法，包括癌症和其他人类和哺乳动物疾病和病况的治疗。更具体地，在首选方面，本发明提供了一种使用戊二烯基半胱氨酸类似物治疗肿瘤、包括牛皮癣、心血管手术后再狭窄、包括肾脏增生的增生、包括类风湿和骨关节炎等慢性炎症疾病的方法。
• PRODRUGS AND CONJUGATES OF PRENYLATION INHIBITORS
  申请人：Borch Richard Frederic

  公开号：US20100249072A1

  公开（公告）日：2010-09-30

  Described herein are neutral prodrugs of phosphorus-containing inhibitors of farnesyl transferase that include one or more phosphate fragments or analogs of phosphate fragments. Analogs of phosphate fragments include various linkers other than oxygen connecting the phosphate fragment to the remaining portion of the drug, such as but not limited to linkers forming phosphoramidates, phosphonates, difluorophosphonates, phosphordiamidates, and the like.

  本文描述了一种醇化酶磷酸转移酶的中性前药，其中包括一个或多个磷酸盐片段或磷酸盐片段的类似物。磷酸盐片段的类似物包括各种连接磷酸盐片段与药物其余部分的氧以外的连接剂，例如但不限于形成磷酰胺酸盐、膦酸盐、二氟膦酸盐、磷酰二胺酸盐等的连接剂。
• Efficient synthesis and biological evaluation of demethyl geranylgeranoic acid derivatives
  作者：Akimori Wada、Fei Wang、Yoshitomo Suhara、Yumiko Yamano、Takashi Okitsu、Kimie Nakagawa、Toshio Okano

  DOI：10.1016/j.bmc.2010.07.003

  日期：2010.8

  Synthetic retinoids have generated in the fields of dermatology and oncology due to their potent anti-proliferative and differentiation activities. We efficiently synthesized different demethyl geranylgeranoic acid (GGA) analogs, and evaluated their biological activities. Among the demethyl analogs synthesized, 3-demethyl derivative exhibited the highest anti-proliferative activity in HL-60 cells. In addition, a 3-demethyl derivative induced apoptosis more potently than 9Z-retinoic acid. These activities were due to the high binding affinity of 3-demethyl derivative for retinoid receptors. We found that, in a conjugated polyene system combined with a methyl substituent, the position of the methyl played an important role in the regulation of gene transcription and apoptosis-inducing activity. These results provided useful information on the structure-activity relationships of GGA derivatives that function as acyclic retinoic acid analogs. This information is likely to be useful in the development of new anti-cancer drugs. (C) 2010 Elsevier Ltd. All rights reserved.