2-methoxy-6-((E)-prop-1-enyl)benzoic acid | 143112-20-3

• 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: 2-methoxy-6-((E)-prop-1-enyl)benzoic acid
• 英文别名: 2-methoxy-6-propenyl-benzoic acid；2-Methoxy-6-ξ-propenyl-benzoesaeure；2-Methoxy-6-propenyl-benzoesaeure；2-methoxy-6-[(E)-prop-1-enyl]benzoic acid
• CAS: 143112-20-3
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: VSKDKRMQMSXCMU-HWKANZROSA-N

物化性质

• 沸点：
  333.8±30.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methoxy-6-((E)-prop-1-enyl)benzoic acid 在 溴 、 溶剂黄146 作用下， 生成 8-hydroxy-3-methyl-1H-isochromen-1-one
  参考文献：
  名称：

  Bendz, Arkiv foer Kemi, 1959, vol. 14, p. 511,513

  摘要：

  DOI：
• 作为产物：
  描述：

  mellein methyl ether 在 氢氧化钾 作用下， 生成 2-methoxy-6-((E)-prop-1-enyl)benzoic acid
  参考文献：
  名称：

  Bendz, Arkiv foer Kemi, 1959, vol. 14, p. 511,513

  摘要：

  DOI：

文献信息

• Ruthenium(II)-Catalyzed Cyclization of Aromatic Acids with Allylic Acetates via Redox-Free Two-Fold Aromatic/Allylic C–H Activations: Combined Experimental and DFT Studies
  作者：Subramanian Jambu、Masilamani Tamizmani、Masilamani Jeganmohan

  DOI：10.1021/acs.orglett.8b00533

  日期：2018.4.6

  A Ru(II)-catalyzed, redox-free, two-fold aromatic/allylic C–H bond activation of aromatic acids with allylic acetates to give (Z)-3-ylidenephthalides is described. In the reaction, H2 was formed as a side product. The detailed mechanistic investigation and DFT studies including the transition-state analysis support the postulate that the C–H allylation takes place at the ortho position of aromatic

  描述了Ru（II）催化的，芳族酸与烯丙基乙酸酯的两倍芳香族/烯丙基C–H键活化，得到（Z）-3-亚萘基。在反应中，形成H 2作为副产物。详细的机理研究和DFT研究（包括过渡态分析）支持以下假设：C–H烯丙基化发生在芳酸与乙酸烯丙酯的邻位，然后通过C（sp 3）–H在烯丙基C（sp 3）–H进行分子内环化。π-烯丙基钌中间体。
• 7-Mesityl-2,2-dimethylindan-1-ol: a novel alcohol which serves as both a chiral auxiliary and a protective group for carboxy functions
  作者：Eiji Koshiishi、Tetsutaro Hattori、Naoki Ichihara、Sotaro Miyano

  DOI：10.1039/b109396g

  日期：2002.1.23

  A novel chiral indanol 11 is conveniently synthesized by using a stepwise displacement of the methoxy groups of 2,6-dimethoxybenzoic ester 1 by a vinyl and then an aryl Grignard reagent as the key step. The racemic indanol 11 is optically resolved as the diastereomeric (Sa)-2′-methoxy-1,1′-binaphthyl-2-carboxylic esters 12 by column chromatography. The absolute stereochemistry of the indanol (+)-11 is established to be S by an X-ray crystallographic analysis of the ester (Sa,S)-12. Performance of the indanol 11 as a chiral auxiliary, and as a protective group for the carboxy function, is examined in the atrolactic acid synthesis from phenylglyoxylic ester 13 and methylmagnesium iodide and in the biphenyl coupling reaction of 2,3-dimethoxybenzoic ester 15 with 2-methoxy-4,6-dimethylphenylmagnesium bromide, resulting in quantitative formations of atrolactic ester 14 with up to 83% de and biphenyl 16 with 72% de, respectively.

  一种新颖的手性吲哚醇11通过逐步置换2,6-二甲氧基苯甲酸酯1中的甲氧基，首先使用苯乙烯Grignard试剂，然后使用芳基Grignard试剂方便地合成。 Racemic 吲哚醇11通过柱色谱被光学分离为二态异构体(Sa)-2'-甲氧基-1,1'-萘基-2-羧酸酯12。通过对酯(Sa,S)-12进行X射线晶体学分析，确定了吲哚醇(+)-11的绝对构型为S。吲哚醇11作为手性辅助试剂及羧基的保护基团的性能在从苯乙酰酸酯13和碘化甲基镁反应合成阿托拉酸中，以及在2,3-二甲氧基苯甲酸酯15与2-甲氧基-4,6-二甲基苯镁溴化物的联苯偶联反应中被检验，结果分别得到在83%对映体过量（de）的阿托拉酸酯14和在72%对映体过量的联苯16的定量生成。
• Novel AlCl₃catalysed syntheses of naturally occurring (±) 8-hydroxy-3-methyl-3,4-dihydroisocoumarins
  作者：Raghao S. Mali、Prakash G. Jagtap、Shrikant R. Patil、Prakash N. Pawar

  DOI：10.1039/c39920000883

  日期：——

  Treatment of (±) 3-ethylphthalides 2 or 2-(prop-1-enyl)benzoic acids 5 with AlCl3 in methylene chloride gives naturally occuring (±) 8-hydroxy-3-methyl-3,4-dihydroisocoumarins 3 in high yields.

  用 AlCl3 在二氯甲烷中处理(±) 3-乙基邻苯二甲酸 2 或 2-(丙-1-烯基)苯甲酸 5，可以高产率地得到天然的(±) 8-羟基-3-甲基-3,4-二氢异香豆素 3。
• Catalytic C–N and C–H Bond Activation: <i>ortho</i>-Allylation of Benzoic Acids with Allyl Amines
  作者：Xiao-Qiang Hu、Zhiyong Hu、Guodong Zhang、Nardana Sivendran、Lukas J. Gooßen

  DOI：10.1021/acs.orglett.8b01762

  日期：2018.7.20

  A facile insertion of ruthenium into aromatic C-H and allylic C-N bonds are the key steps in a [Ru(p-cymene)Cl-2](2)-catalyzed ortho-C-H allylation of benzoic acids. This protocol allows drawing on the large pool of allylic amines for state-of-the-art ortho-functionalizations of arenes, turning neutral amines into leaving groups. Concise syntheses of biologically active compounds provide further evidence of the synthetic potential of this methodology.
• Yabuta; Sumiki, Nippon Nogeikagaku Kaishi, 1934, vol. 10, p. 703,709
  作者：Yabuta、Sumiki

  DOI：——

  日期：——