2-(hydroxy(3-nitrophenyl)methyl)acrylic acid butyl ester | 627882-13-7

• 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-(hydroxy(3-nitrophenyl)methyl)acrylic acid butyl ester
• 英文别名: Butyl 2-[hydroxy-(3-nitrophenyl)methyl]prop-2-enoate
• CAS: 627882-13-7
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: UGLLWOHIAJAIDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  89.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(hydroxy(3-nitrophenyl)methyl)acrylic acid butyl ester 在 吡啶 、 三乙烯二胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.25h， 生成 2-[(3-nitrophenyl)phenoxymethyl]acrylic acid butyl ester
  参考文献：
  名称：

  The Baylis–Hillman chemistry in aqueous media: elucidation of mechanism for synthesis of ether side-product leads to an efficient approach to C–O bond formation

  摘要：

  The formation of an ether from the Baylis-Hillman (BH) adduct during the BH reaction of 5-isoxazolecarboxaldehydes is a common phenomenon if the reaction is allowed to proceed for longer periods. The amount of formation of such ethers depends on the acrylates used and is most significant for tert-butyl acrylates. A study of the plausible mechanism for the formation of these side-products led to reactions of acetates of BH adducts with phenol in aqueous media to yield the corresponding 3-phenoxy alk-2-enoates in good yields. The successful translation of solution phase methodology to solid phase for application towards combinatorial chemistry is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01561-2
• 作为产物：
  描述：

  丙烯酸丁酯 、 间硝基苯甲醛 在 三乙烯二胺 作用下， 反应 0.33h， 生成 2-(hydroxy(3-nitrophenyl)methyl)acrylic acid butyl ester
  参考文献：
  名称：

  The Baylis–Hillman chemistry in aqueous media: elucidation of mechanism for synthesis of ether side-product leads to an efficient approach to C–O bond formation

  摘要：

  The formation of an ether from the Baylis-Hillman (BH) adduct during the BH reaction of 5-isoxazolecarboxaldehydes is a common phenomenon if the reaction is allowed to proceed for longer periods. The amount of formation of such ethers depends on the acrylates used and is most significant for tert-butyl acrylates. A study of the plausible mechanism for the formation of these side-products led to reactions of acetates of BH adducts with phenol in aqueous media to yield the corresponding 3-phenoxy alk-2-enoates in good yields. The successful translation of solution phase methodology to solid phase for application towards combinatorial chemistry is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01561-2

文献信息

• NaBH₄-mediated FacileReduction of Esters of Baylis-Hillman Adducts: An EfficientApproach to Substituted Propane-1,3-Diols
  作者：Sanjay Batra、Arundhati Patra、Amiya P. Bhaduri

  DOI：10.1055/s-2003-40992

  日期：——

  Reduction of the ester group in the Baylis-Hillman adductsby NaBH4 reduction is facilitated by the secondary hydroxyl grouppresent at their β-position. This method is efficient forthe preparation of substituted propane-1,3-diols.

  通过 NaBH4 还原法还原 Baylis-Hillman 加合物中的酯基时，其 δ 位上存在的仲羟基会起到促进作用。这种方法可以有效地制备取代的丙烷-1,3-二醇。
• Baylis–Hillman reaction promoted by a recyclable protic-ionic-liquid solvent–catalyst system: DABCO–AcOH–H2O
  作者：Ying Song、Haihua Ke、Nan Wang、Limin Wang、Gang Zou

  DOI：10.1016/j.tet.2009.09.049

  日期：2009.11

  A recyclable protic-ionic-liquid solvent-catalyst system, DABCO-AcOH-H2O, has been developed and used in the Baylis-Hillman reaction of aromatic aldehydes, aliphatic aldehydes, and cinnamaldehydes with acrylates and acrylonitrile, showing comparable performance to free DABCO in traditional solvents. The DABCO-AcOH-H2O solvent-catalyst system could be reused for at least five times without significant loss of activity. (C) 2009 Elsevier Ltd. All rights reserved.