4-benzyloxy-3-methylbut-2-enoic acid methyl ester | 310887-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-benzyloxy-3-methylbut-2-enoic acid methyl ester
• 英文别名: (2E)-3-Methyl-4-(benzyloxy)-2-butenoic Acid Methyl Ester；methyl (E)-3-methyl-4-phenylmethoxybut-2-enoate
• CAS: 310887-98-0
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: QHMCFYFWVUBHQT-DHZHZOJOSA-N

物化性质

• 沸点：
  316.8±30.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-3-methylbut-2-enoic acid methyl ester 在 palladium on activated charcoal titanium(IV) isopropylate 、 sodium hydroxide 、 氢气 、 二异丁基氢化铝 、 (+)-Weinsaeure-diethylester 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 26.25h， 生成 2-C-甲基-赤藓糖醇
  参考文献：
  名称：

  Simple and versatile synthesis of branched polyols: (+)-2-C-methylerythritol and (+)-2-C-methylthreitol

  摘要：

  The paper reports a new approach for the enantioselective synthesis of 2-C-methyl tetrols. The procedure has been utilized for preparing methylthreitol and methylerythritol, a putative intermediate in the mevalonate-independent biosynthesis of terpenoids in bacteria, algae and higher plants. The methodology offers straightforward access to related compounds and isotopically labeled derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01296-x
• 作为产物：
  描述：

  methyl (E)-3-formylcrotonate 在 sodium tetrahydroborate 、 三氟甲磺酸 作用下， 以 甲醇 、 二氯甲烷 、 环己烷 为溶剂， 反应 3.0h， 生成 4-benzyloxy-3-methylbut-2-enoic acid methyl ester
  参考文献：
  名称：

  Concise Synthesis of (+)-2-C-Methyl-d-erythritol-4-phosphate

  摘要：

  DOI：

  10.1021/jo005732o

文献信息

• Synthesis of 4-Diphosphocytidyl-2-<i>C</i>-methyl-<scp>d</scp>-erythritol and 2-<i>C</i>-Methyl-<scp>d</scp>-erythritol-4-phosphate
  作者：Andrew T. Koppisch、C. Dale Poulter

  DOI：10.1021/jo025736o

  日期：2002.7.1

  2-C-Methyl-D-erythritol 4-phosphate (MEP, 2) and 4-diphosphocytidyl-2-C-methyl-D-erythritol (CDPME, 3) are metabolites in the MEP pathway for biosynthesis of isoprenoid compounds in bacteria, plant chloroplasts, and algae. The free phosphoacid of 2 was prepared from benzyloxyacetone in five steps with an overall yield of 27% and an enantiomeric ratio (er) of 75:25. Following titration to the corresponding tributylammonium salt, 2 was coupled to cytidine 5'-monophosphate using a protocol originally developed for synthesis of base-sensitive nucleoside diphosphate sugars to give 3 in 40% yield, following purification by size exclusion chromatography.
• HENDRICKSON, J. B.;BOUDREAUX, G. J.;PALUMBO, P. S., J. AMER. CHEM. SOC., 1986, 108, N 9, 2358-2366
  作者：HENDRICKSON, J. B.、BOUDREAUX, G. J.、PALUMBO, P. S.

  DOI：——

  日期：——
• Evidence for the Biosynthesis of Squalene via the Methylerythritol Phosphate Pathway in a <i>Streptomyces</i> sp. Obtained from a Marine Sediment
  作者：Angelo Fontana、Michael T. Kelly、James D. Prasad、Raymond J. Andersen

  DOI：10.1021/jo015751d

  日期：2001.9.1
• Simple and versatile synthesis of branched polyols: (+)-2-C-methylerythritol and (+)-2-C-methylthreitol
  作者：Angelo Fontana、Rossella Messina、Aldo Spinella、Guido Cimino

  DOI：10.1016/s0040-4039(00)01296-x

  日期：2000.9

  The paper reports a new approach for the enantioselective synthesis of 2-C-methyl tetrols. The procedure has been utilized for preparing methylthreitol and methylerythritol, a putative intermediate in the mevalonate-independent biosynthesis of terpenoids in bacteria, algae and higher plants. The methodology offers straightforward access to related compounds and isotopically labeled derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Concise Synthesis of (+)-2-<i>C</i>-Methyl-<scp>d</scp>-erythritol-4-phosphate
  作者：Angelo Fontana

  DOI：10.1021/jo005732o

  日期：2001.4.1