(E)-methyl 4-(oct-1-en-1-yl)benzoate | 158937-15-6

• 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: (E)-methyl 4-(oct-1-en-1-yl)benzoate
• 英文别名: (E)-methyl 4-(oct-1-enyl)benzoate；methyl 4-(oct-1-enyl)benzoate
• CAS: 158937-15-6
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: IAGHFZPPOQEFIW-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-methyl 4-(oct-1-en-1-yl)benzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 4-(oct-1-enyl)benzoic acid
  参考文献：
  名称：

  Amphipathic benzoic acid derivatives: Synthesis and binding in the hydrophobic tunnel of the zinc deacetylase LpxC

  摘要：

  The first committed step in lipid A biosynthesis is catalyzed by uridine diphosphate-(3-O-(R-3-hydroxymyristoyl))--Nacetylglucosamine deacetylase (LpxC), a zinc-dependent deacetylase, and inhibitors of LpxC may be useful in the development of antibacterial agents targeting a broad spectrum of Gram-negative bacteria. Here, we report the design of amphipathic benzoic acid derivatives that bind in the hydrophobic tunnel in the active site of LpxC. The hydrophobic tunnel accounts for the specificity of LpxC toward substrates and substrate andlogues bearing a 3-O-myristoyl substituent. Simple benzoic acid derivatives bearing an aliphatic 'tail' bind in the hydrophobic tunnel with micromolar affinity despite the lack of a glucosamine ring like that of the substrate. However, although these benzoic acid derivatives each contain a negatively charged carboxylate 'warhead' intended to coordinate to the active site zinc ion, the 2.25 angstrom resolution X-ray crystal structure of LpxC complexed with 3-(heptyloxy)benzoate reveals 'backward' binding in the hydrophobic tunnel, such that the benzoate moiety does not coordinate to zinc. Instead, it binds at the outer end of the hydrophobic tunnel. Interestingly, these ligands bind with affinities comparable to those measured for more complicated substrate analogue inhibitors containing glucosamine ring analogues and hydroxamate 'warheads' that coordinate to the active site zinc ion. We conclude that the intermolecular interactions in the hydrophobic tunnel dominate enzyme affinity in this series of benzoic acid derivatives. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2007.01.044
• 作为产物：
  描述：

  正庚基三苯基溴化磷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以85%的产率得到(E)-methyl 4-(oct-1-en-1-yl)benzoate
  参考文献：
  名称：

  Amphipathic benzoic acid derivatives: Synthesis and binding in the hydrophobic tunnel of the zinc deacetylase LpxC

  摘要：

  The first committed step in lipid A biosynthesis is catalyzed by uridine diphosphate-(3-O-(R-3-hydroxymyristoyl))--Nacetylglucosamine deacetylase (LpxC), a zinc-dependent deacetylase, and inhibitors of LpxC may be useful in the development of antibacterial agents targeting a broad spectrum of Gram-negative bacteria. Here, we report the design of amphipathic benzoic acid derivatives that bind in the hydrophobic tunnel in the active site of LpxC. The hydrophobic tunnel accounts for the specificity of LpxC toward substrates and substrate andlogues bearing a 3-O-myristoyl substituent. Simple benzoic acid derivatives bearing an aliphatic 'tail' bind in the hydrophobic tunnel with micromolar affinity despite the lack of a glucosamine ring like that of the substrate. However, although these benzoic acid derivatives each contain a negatively charged carboxylate 'warhead' intended to coordinate to the active site zinc ion, the 2.25 angstrom resolution X-ray crystal structure of LpxC complexed with 3-(heptyloxy)benzoate reveals 'backward' binding in the hydrophobic tunnel, such that the benzoate moiety does not coordinate to zinc. Instead, it binds at the outer end of the hydrophobic tunnel. Interestingly, these ligands bind with affinities comparable to those measured for more complicated substrate analogue inhibitors containing glucosamine ring analogues and hydroxamate 'warheads' that coordinate to the active site zinc ion. We conclude that the intermolecular interactions in the hydrophobic tunnel dominate enzyme affinity in this series of benzoic acid derivatives. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2007.01.044

文献信息

• General and User-friendly Method for Suzuki Reactions with Aryl Chlorides
  作者：Alois Fürstner、Andreas Leitner

  DOI：10.1055/s-2001-10763

  日期：——

  Through the use of Pd(OAc)2 and the sterically hindered imidazolium salt 5 (IPr · HCl) as the pre-catalyst mixture, aryl chlorides undergo efficient cross coupling reactions with 9-R-9-BBN derivatives (R = alkyl, allyl, alkynyl, cyclopropyl) in the presence of KOMe as the base. This procedure is easily scaleable and applies to electron poor and electron rich substrates with similar ease.

  通过使用Pd(OAc)2和空间位阻较大的咪唑盐5（IPr · HCl）作为预催化剂混合物，在KOMe作为碱的存在下，芳基氯与9-R-9-BBN衍生物（R = 烷基、烯丙基、炔基、环丙基）发生高效的交叉偶联反应。该方法易于放大，并且对电子贫乏和电子丰富的底物都同样适用。
• ZrCl2(η-C5Me5)2-AlHCl2·(THF)2: efficient hydroalumination of terminal alkynes and cross-coupling of the derived alanes
  作者：Philip Andrews、Christopher M. Latham、Marc Magre、Darren Willcox、Simon Woodward

  DOI：10.1039/c2cc37537k

  日期：——

  with exceptional chemo-, regio- and stereoselectivity under efficient ZrCl(2)(eta-C(5)Me(5))(2) catalysis (2-5 mol%). The resulting vinyl alanes undergo palladium cross-coupling with a wide range of sp(2) electrophiles (aryl, heteroaryl and vinyl halides/pseudohalides) in good to excellent yields.

  稳定的AlHCl（2）。（THF）（2）在高效ZrCl（2）（eta-C（5）Me（5））（2）催化下，与CH相同的RC具有与CH相同的氢氧化铝，具有出色的化学，区域和立体选择性（2- 5mol％）。生成的乙烯基丙氨酸与各种sp（2）亲电试剂（芳基，杂芳基和乙烯基卤化物/拟卤化物）进行钯交叉偶联，收率良好。
• Palladium-Tetraphosphine Catalysed Heck Reaction with Simple Alkenes: Influence of Reaction Conditions on the Migration of the Double Bond
  作者：Henri Doucet、Maurice Santelli、Yacoub Fall、Florian Berthiol

  DOI：10.1055/s-2007-966063

  日期：2007.6

  The Heck reaction of aryl halides with simple alk-1-enes is a powerful method for the synthesis of ( E)-1-arylalk-1-ene derivatives. The major problem of this reaction is the palladium-catalysed migration of the carbon-carbon double bond along the alkyl chain. We observed that this migration could be partially controlled using appropriate reaction conditions. The ramification of the alkyl chain and

  芳基卤化物与简单的 alk-1-enes 的 Heck 反应是合成 (E)-1-arylalk-1-ene 衍生物的有效方法。该反应的主要问题是钯催化的碳-碳双键沿烷基链的迁移。我们观察到使用适当的反应条件可以部分控制这种迁移。烷基链的分支和芳基卤化物上的取代基对这种迁移也有重要影响。CIS, CIS, CIS-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/[Pd(C 3 H 5 )Cl] 2 体系有效催化多种芳基卤化物与直链烯烃的 Heck 反应-1-烯和癸-1-烯或支链烯烃4-甲基己-1-烯、5-甲基己-1-烯、烯丙基环戊烷或烯丙基环己烷。大多数情况下，获得了 70-80% 的选择性。在某些情况下，可以观察到高达 97% 有利于 (E)-1-arylalk-1-enes。此外，可以使用非常低的催化剂负载量进行几个反应。