ethyl (E)-6-<(dimethyl-tert-butylsilyl)oxy>-3-methyl-2-hexenoate | 118607-87-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-6-<(dimethyl-tert-butylsilyl)oxy>-3-methyl-2-hexenoate
• 英文别名: ethyl 6-<(tert-butyldimethylsilyl)oxy>-3-methyl-2(E)-hexenoate；(E)-ethyl 6-(tert-butyldimethylsilyloxy)-3-methylhex-2-enoate；Ethyl(E)-6-O-tert-butyldimethylsilyl-3-methyl-2-hexenoate；ethyl (E)-6-[tert-butyl(dimethyl)silyl]oxy-3-methylhex-2-enoate
• CAS: 118607-87-7
• 化学式: C₁₅H₃₀O₃Si
• 分子量: 286.487
• InChiKey: TZJWMTMGLUDBOT-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (E)-6-<(dimethyl-tert-butylsilyl)oxy>-3-methyl-2-hexenoate 在 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 titanium(IV) isopropylate 、 sodium tetrahydroborate 、 四丙基高钌酸铵 、 草酰氯 、 bis(cyclopentadienyl)titanium (III) chloride 、 偶氮二异丁腈 、 L-(+)-酒石酸二异丙酯 、 cerium(III) chloride heptahydrate 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 碘 、 三甲基铝 、 三正丁基氢锡 、 双(三甲基硅烷基)氨基钾 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 97.16h， 生成 (3aS*,5aR*,8aR*,8bR*)-5a-methyloctahydro-2H-indeno[5,4-b]furan-2,8(1H)-dione
  参考文献：
  名称：

  Formal synthesis of degraded sterol (+)-aplykurodinone-1

  摘要：

  The formal synthesis of aplykurodinone-1 is accomplished starting from a suitably functionalized bicyclic lactone having the requisite cis-fused ring junction with a quaternary chiral center that was assembled following a Cp2TiCl-mediated radical cyclization protocol. Our synthetic route further elaborates implementation of Grubbs ring closing metathesis (RCM), Eschenmoser-Claisen rearrangement and iodo-lactonization reactions for the synthesis of the final tricyclic precursor of the target molecule. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.026
• 作为产物：
  描述：

  5-羟基-2-戊酮 在 咪唑 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 ethyl (E)-6-<(dimethyl-tert-butylsilyl)oxy>-3-methyl-2-hexenoate
  参考文献：
  名称：

  丙酮酸及其衍生物的合成途径

  摘要：

  探索了到环戊酸衍生物的合成途径，并描述了这些分子全部合成的收敛途径。

  DOI：

  10.1016/s0040-4020(01)85090-0

文献信息

• Synthesis and Liver Microsomal Metabolic Stability Studies of a Fluorine‐Substituted δ‐Tocotrienol Derivative
  作者：Xingui Liu、Saikat Poddar、Lin Song、Howard Hendrickson、Xuan Zhang、Yaxia Yuan、Daohong Zhou、Guangrong Zheng

  DOI：10.1002/cmdc.201900676

  日期：2020.3.18

  A fluoro-substituted δ-tocotrienol derivative, DT3-F2, was synthesized. This compound was designed to stabilize the metabolically labile terminal methyl groups of δ-tocotrienol by replacing one C-H bond on each of the two methyl groups with a C-F bond. However, in vitro metabolic stability studies using mouse liver microsomes revealed an unexpected rapid enzymatic C-F bond hydrolysis of DT3-F2. To

  合成了氟取代的δ-生育三烯酚衍生物DT3-F2。该化合物被设计为通过用CF键取代两个甲基上每个的一个CH键来稳定δ-生育三烯酚的代谢不稳定的甲基。但是，使用小鼠肝微粒体进行的体外代谢稳定性研究表明，DT3-F2发生了意外的快速酶促CF键水解。据我们所知，这是烯丙基CF键异常代谢水解的第一个报道。
• Synthesis of Sulfur- and Sulfoxide-Substituted 2,3-Oxidosqualenes and Their Evaluation as Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase
  作者：Yi Feng Zheng、Allan C. Oehlschlager、Nafsika H. Georgopapadakou、Peter G. Hartman、Petra Scheliga

  DOI：10.1021/ja00107a011

  日期：1995.1

  2,3-Oxidosqualene (23-OS) analogs that contain thioether (52-55) and sulfoxide (56-60) at positions normally occupied by carbons considered to be cationic during 2,3-oxidosqualene-lanosterol cyclase (OSC) cyclization (C-6, C-10, C-14, and C-19) were synthesized and tested as substrate mimic inhibitors of fungal and mammalian OSC. The analogs were found to be potent inhibitors of cyclase in cell-free extracts of Candida albicans and rat liver. Thioether analogs were more potent than the corresponding sulfoxides. In both series, those 2,3-OS analogs containing a sulfur at the position normally occupied by C-19 were the most potent. With C. albicans cyclase, the IC50 for thioether 55 was 0.0023 mu M while 60 exhibited an IC50 of 0.065 mu M, which are the lowest values reported for a inhibitor of this enzyme. Similarly, thioether 55 displayed an IC50 of 0.00082 mu M for rat liver cyclase which is the best inhibitor up to date for this enzyme. These results suggest that mimics with modification in the region of C-19 of 2,3-OS have a high affinity for the active site of these enzymes. The same series of analogs (52-60) were also tested for inhibition of cholesterol biosynthesis in intact MDBK (Madin Darbin bovine kidney) cells and for in vitro antifungal activity against C. albicans.
• A Simple Synthesis of (<i>R</i>)(<i>S)(E)</i>-3,7-Dimethyl-2-octene-1,8-dioc Acid, a Copulation Release Pheromone Component of the Azuki Bean Weevil
  作者：Elisabetta Adorni Fontana、Adriano Carpita、Elena Rossi

  DOI：10.1080/00397919308012599

  日期：1993.11

  (R)(S)(E)-3,7-dimethyl-2-octene-1,8-dioic acid, (R)(S)(E)-1, also named callosobruchusic acid, has been synthetized in five steps using a simple reaction sequence based on the zirconium-catalyzed methylalumination of commercially available 4-pentyn-1-ol, 2a, or its O-tert-butyldimethylsilyl ether, 2b.
• CHIARELLO, JACK;JOULLIE, MADELEINE M., TETRAHEDRON, 44,(1988) N 1, 41-48
  作者：CHIARELLO, JACK、JOULLIE, MADELEINE M.

  DOI：——

  日期：——