methyl 2-(4-oxobutyl)benzoate | 615581-25-4

• 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: methyl 2-(4-oxobutyl)benzoate
• 英文别名: 2-(4-oxobutyl)benzoic acid methyl ester
• CAS: 615581-25-4
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: NLADAYDTGCXOOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-oxobutyl)benzoate 在 2,6-二甲基吡啶 、 正丁基锂 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 36.5h， 生成
  参考文献：
  名称：

  OSB-AMP 的稳定类似物：MenE 的强效抑制剂，来自细菌甲萘醌生物合成的邻琥珀酰苯甲酸辅酶 A 合成酶

  摘要：

  探戈需要两个人： OSB-AMS 侧链上的游离羧酸盐和酮部分对于有效抑制酰基辅酶 A 合成酶 MenE 至关重要，这是一种有前途的新抗菌靶点。

  DOI：

  10.1002/cbic.201100585
• 作为产物：
  描述：

  2-(1,3-二氧戊环-2-基)乙基三苯基溴化磷 在 palladium on activated charcoal 氢气 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 生成 methyl 2-(4-oxobutyl)benzoate
  参考文献：
  名称：

  Samarium(II)-Promoted Radical Spirocyclization onto an Aromatic Ring

  摘要：

  Samarium(II)-mediated spirocyclization onto an aromatic ring was achieved by the reaction of methyl 4-(4-oxoalkyl)benzoates with SmI2 in the presence of i-PrOH and HMPA, yielding methyl 1-alkyl-1-hydroxyspiro[4.5]dec-6-ene-8-carboxylates in moderate to high yields. Utilizing this chemistry, spiro[3.5] and -[5.5] systems, and sterically congested spiro[4.5] systems, were easily synthesized. For the successful conversion, appropriate activation of the aromatic ring has proven to be extremely important: while an ester or amide functionality on the aromatic ring can promote the spirocyclization, a sulfonamide substituent causes ortho cyclization.

  DOI：

  10.1021/jo034767w

文献信息

• [EN] PREPARATION OF 3,3-DIALKXOY-1-METHYLENEPROPYL ARENES<br/>[FR] PRÉPARATION DE 3,3-DIALKOXY-1-MÉTHYLÈNEPROPYL ARÈNES
  申请人：LONZA AG

  公开号：WO2012150281A1

  公开（公告）日：2012-11-08

  The invention discloses a method for the preparation of 3,3-dialkxoy-1-methylenepropyl arenes from crotonaldehyde and aryldiazonium salts, and intermediates for the preparation of perfumes.

  该发明公开了一种从己烯醛和芳基重氮盐制备3,3-二烷氧基-1-亚甲基丙基芳烃的方法，以及用于制备香水的中间体。
• [EN] PREPARATION OF 4,4-DIALKOXY-1-BUTEN-1-YLARENES<br/>[FR] PRÉPARATION DE 4,4-DIALCOXY-1-BUTÈNE-1-YLARÈNES
  申请人：LONZA AG

  公开号：WO2012150280A3

  公开（公告）日：2013-01-10
• Direct C-4 arylation of crotonaldehyde with arenediazonium tetrafluoroborates
  作者：Florencio Zaragoza、Verena Heinze

  DOI：10.1016/j.tetlet.2011.07.005

  日期：2011.9

  Arenediazonium tetrafluoroborates react with crotonaldehyde (2-butenal) in methanol in the presence of catalytic amounts of Pd(OAc)(2) to yield mainly 4,4-dimethoxy-1-butenylarenes. In most of the examples studied, small amounts of an isomeric byproduct were formed, presumably 3,3-dimethoxy-1-methylene-propylarenes. Because crotonaldehyde and arenediazonium salts are cheap and readily available, this reaction is a convenient access to protected 4-arylbutenals. (C) 2011 Elsevier Ltd. All rights reserved.
• Samarium(II)-Promoted Radical Spirocyclization onto an Aromatic Ring
  作者：Hiroaki Ohno、Mitsuaki Okumura、Shin-ichiro Maeda、Hiroki Iwasaki、Ryutaro Wakayama、Tetsuaki Tanaka

  DOI：10.1021/jo034767w

  日期：2003.10.1

  Samarium(II)-mediated spirocyclization onto an aromatic ring was achieved by the reaction of methyl 4-(4-oxoalkyl)benzoates with SmI2 in the presence of i-PrOH and HMPA, yielding methyl 1-alkyl-1-hydroxyspiro[4.5]dec-6-ene-8-carboxylates in moderate to high yields. Utilizing this chemistry, spiro[3.5] and -[5.5] systems, and sterically congested spiro[4.5] systems, were easily synthesized. For the successful conversion, appropriate activation of the aromatic ring has proven to be extremely important: while an ester or amide functionality on the aromatic ring can promote the spirocyclization, a sulfonamide substituent causes ortho cyclization.
• Stable Analogues of OSB-AMP: Potent Inhibitors of MenE, the o-Succinylbenzoate-CoA Synthetase from Bacterial Menaquinone Biosynthesis
  作者：Xuequan Lu、Rong Zhou、Indrajeet Sharma、Xiaokai Li、Gyanendra Kumar、Subramanyam Swaminathan、Peter J. Tonge、Derek S. Tan

  DOI：10.1002/cbic.201100585

  日期：2012.1.2

  It takes two to tango: Both the free carboxylate and ketone moieties on the side chain of OSB‐AMS are critical for potent inhibition of the acyl‐CoA synthetase MenE, a promising new antibacterial target.

  探戈需要两个人： OSB-AMS 侧链上的游离羧酸盐和酮部分对于有效抑制酰基辅酶 A 合成酶 MenE 至关重要，这是一种有前途的新抗菌靶点。