benzyl 4-ethanoic acid-3,5-dimethylpyrrole-2-carboxylate | 869337-75-7

• 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: benzyl 4-ethanoic acid-3,5-dimethylpyrrole-2-carboxylate
• 英文别名: benzyl 3,5-dimethyl-4-(ethanoic acid)pyrrole-2-carboxylate；2-(2,4-dimethyl-5-phenylmethoxycarbonyl-1H-pyrrol-3-yl)acetic acid
• CAS: 869337-75-7
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: XQFIVJJGSBKHSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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 4-ethanoic acid-3,5-dimethylpyrrole-2-carboxylate 在 palladium on activated charcoal 氢气 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成
  参考文献：
  名称：

  Asymmetric Synthesis of Mono- and Dinuclear Bis(dipyrrinato) Complexes

  摘要：

  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.

  DOI：

  10.1021/jo070569j
• 作为产物：
  描述：

  benzyl 4-<(methoxycarbonyl)methyl>-3,5-dimethylpyrrole-2-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以91%的产率得到benzyl 4-ethanoic acid-3,5-dimethylpyrrole-2-carboxylate
  参考文献：
  名称：

  吡啶二酮的高度非对映选择性模板化络合物。

  摘要：

  [反应：见正文]具有相对长的间隔基（> 5个原子）的Bis（dipyrromethene）s形成螺旋单体配合物，因为bi（dipyrromethene）的两个结合单元在相同的四面体配位金属离子周围螯合。本文中，我们报道了使用高手性二元醇和酒石酸酯基序作为连接子和不对称模板的双（二吡咯亚甲基）s的第一个高度非对映选择性单核螺旋形成络合物反应。

  DOI：

  10.1021/ol052044o

文献信息

• 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.
• Highly Diastereoselective Templated Complexation of Dipyrromethenes
  作者：Adeeb Al-Sheikh-Ali、Kyle S. Cameron、T. Stanley Cameron、Katherine N. Robertson、Alison Thompson

  DOI：10.1021/ol052044o

  日期：2005.10.1

  [reaction: see text] Bis(dipyrromethene)s with relatively long spacers (>5 atoms) form helical monomeric complexes as the two binding units of the bis(dipyrromethene) chelate around the same tetrahedrally coordinated metal ion. Herein we report the first highly diastereoselective mononuclear helicate-forming complexation reactions of bis(dipyrromethene)s using homochiral binol and tartrate motifs which

  [反应：见正文]具有相对长的间隔基（> 5个原子）的Bis（dipyrromethene）s形成螺旋单体配合物，因为bi（dipyrromethene）的两个结合单元在相同的四面体配位金属离子周围螯合。本文中，我们报道了使用高手性二元醇和酒石酸酯基序作为连接子和不对称模板的双（二吡咯亚甲基）s的第一个高度非对映选择性单核螺旋形成络合物反应。
• 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.