benzyl 3,5-dimethyl-4-(propanoic acid)pyrrole-2-carboxylate | 852160-79-3

• 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: benzyl 3,5-dimethyl-4-(propanoic acid)pyrrole-2-carboxylate
• 英文别名: 4-(2-carboxyethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid benzyl ester；benzyl 3,5-dimethyl-4-propionic acid-pyrrole-2-carboxylate；3-(2,4-dimethyl-5-phenylmethoxycarbonyl-1H-pyrrol-3-yl)propanoic acid
• CAS: 852160-79-3
• 化学式: C₁₇H₁₉NO₄
• 分子量: 301.342
• InChiKey: RJEXRGIOADWRKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  79.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 3,5-dimethyl-4-(propanoic acid)pyrrole-2-carboxylate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢溴酸 、 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 64.33h， 生成
  参考文献：
  名称：

  Dinuclear Zinc(II) Double-Helicates of Homochirally Substituted Bis(dipyrromethene)s

  摘要：

  A series of bis(dipyrromethene)s substituted with aromatic amide and aliphatic ester homochiral auxiliaries have been prepared and complexed with zinc(II) ions to form double-helical dinuclear complexes. CD analysis of the crude complexes revealed that the helicates formed in a diastereo-selective manner. The helicates have been resolved into their constituent M and P helices by HPLC, indicating that the helical sense of the complexes is stable to racemization.

  DOI：

  10.1021/jo051727e
• 作为产物：
  描述：

  2,4-二甲基-5-乙氧羰基-3-吡咯丙酸乙酯 在 sodium hydroxide 、 sodium 作用下， 以 乙醇 为溶剂， 60.0~100.0 ℃ 、2.0 kPa 条件下， 反应 9.5h， 生成 benzyl 3,5-dimethyl-4-(propanoic acid)pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis of Orthogonally Protected Pyrrole Tricarboxylic Acid Derivatives: Versatile Building Blocks for Pyrrole-Containing Compounds

  摘要：

  本文描述了三种新的正交保护吡咯三羧酸盐 1-3 的大规模合成。利用不同的裂解条件，这三种羧酸盐中的每一种都可以选择性地游离出来而不影响其他羧酸盐，从而使这些吡咯衍生物成为天然产物或超分子化学领域应用广泛的多功能合成构筑基块。

  DOI：

  10.1055/s-2005-918435

文献信息

• Asymmetric Synthesis of Mono- and Dinuclear Bis(dipyrrinato) Complexes
  作者：Adeeb Al-Sheikh Ali、Ronald E. Benson、Sascha Blumentritt、T. Stanley Cameron、Anthony Linden、David Wolstenholme、Alison Thompson

  DOI：10.1021/jo070569j

  日期：2007.6.1

  The diastereoselective syntheses of Zn(II) bis(dipyrrinato) helicates is reported, involving ligands templated by the incorporation of homochiral binol within the linker joining the two dipyrrinato units. The most diastereoselective formation of dinuclear bis(dipyrrinato) helicates to date is reported. The formation of either mononuclear or dinuclear helicates can be tuned by varying the length of the linker between the dipyrrinato units and by varying the complexation procedure. The neutral dipyrrinato helicates were readily analyzed by HPLC to ascertain diastereoselectivity, and circular dichroism studies revealed the helical nature of the complexes. The molar ellipticities of the helicates produced by diastereoselective complexation are very large in the visible region and typically correspond to binol moieties in the UV region. Extensive X-ray crystallographic investigations further confirmed the helicity of the mononuclear Zn(II) helicates and identified significant interlayer displacement and bending within crystals.
• Stereochemically Stable Double-Helicate Dinuclear Complexes of Bis(dipyrromethene)s:  A Chiroptical Study
  作者：Tabitha E. Wood、Nathan D. Dalgleish、Erin D. Power、Alison Thompson、Xiaoming Chen、Yoshio Okamoto

  DOI：10.1021/ja0500613

  日期：2005.4.1

  Helical zinc(II) complexes of bis(dipyrromethene)s bearing homochiral amide substituents were synthesized. Analysis of the products by chiral HPLC showed two diastereomeric major products and showed that dipyrromethene double-nuclear helicates are stereochemically stable and do not interconvert. Circular dichroism (CD) studies showed that the complexation reactions had proceeded with modest diastereomeric excesses. Analysis of an analogous symmetric zinc(II) bis(dipyrromethene) lacking homochiral substituents that could act as chromophores discounted induced CD by the chiral auxiliaries.
• Dinuclear Zinc(II) Double-Helicates of Homochirally Substituted Bis(dipyrromethene)s
  作者：Tabitha E. Wood、Avena C. Ross、Nathan D. Dalgleish、Erin D. Power、Alison Thompson、Xiaoming Chen、Yoshio Okamoto

  DOI：10.1021/jo051727e

  日期：2005.11.1

  A series of bis(dipyrromethene)s substituted with aromatic amide and aliphatic ester homochiral auxiliaries have been prepared and complexed with zinc(II) ions to form double-helical dinuclear complexes. CD analysis of the crude complexes revealed that the helicates formed in a diastereo-selective manner. The helicates have been resolved into their constituent M and P helices by HPLC, indicating that the helical sense of the complexes is stable to racemization.
• Synthesis of Orthogonally Protected Pyrrole Tricarboxylic Acid Derivatives: Versatile Building Blocks for Pyrrole-Containing Compounds
  作者：Carsten Schmuck、Daniel Rupprecht、Christian Urban、Nicholas Walden

  DOI：10.1055/s-2005-918435

  日期：——

  The large-scale synthesis of three new orthogonally protected pyrrole tricarboxylates 1-3 is described. Using different cleavage conditions, each of the three carboxylates can be set free selectively without affecting the others, making these pyrrole derivatives versatile synthetic building blocks for a wide range of applications in natural product or supramolecular chemistry.

  本文描述了三种新的正交保护吡咯三羧酸盐 1-3 的大规模合成。利用不同的裂解条件，这三种羧酸盐中的每一种都可以选择性地游离出来而不影响其他羧酸盐，从而使这些吡咯衍生物成为天然产物或超分子化学领域应用广泛的多功能合成构筑基块。