4-Ethyl-5-(4-ethyl-5-formyl-3-methyl-1H-pyrrol-2-ylmethyl)-3-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester | 145696-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-Ethyl-5-(4-ethyl-5-formyl-3-methyl-1H-pyrrol-2-ylmethyl)-3-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 4-ethyl-5-[(4-ethyl-5-formyl-3-methyl-1H-pyrrol-2-yl)methyl]-3-methyl-1H-pyrrole-2-carboxylate
• CAS: 145696-59-9
• 化学式: C₂₁H₃₀N₂O₃
• 分子量: 358.481
• InChiKey: OASDBCXXYZNMPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  75
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Ethyl-5-(4-ethyl-5-formyl-3-methyl-1H-pyrrol-2-ylmethyl)-3-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester 在 盐酸 、 对甲苯磺酸 、 三乙胺 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Synthesis of deoxophylloerythroetioporphyrin (DPEP) and three ring homologs by an improved b-bilene methodology

  摘要：

  Deoxophylloerythroetioporphyrin, an important porphyrin molecular fossil from oil shales and petroleum, and three homologs with six-, seven- or eight-membered exocyclic rings have been prepared by a one pot cyclization of b-bilenes with TFA-trimethyl orthoformate in dichloromethane. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01960-1
• 作为产物：
  描述：

  tert-butyl 4-ethyl-3-methyl-1H-pyrrole-2-carboxylate 在 palladium on activated charcoal montmorillonite clay 、 氢气 、 苯甲酰氯 、 对甲苯磺酸 作用下， 生成 4-Ethyl-5-(4-ethyl-5-formyl-3-methyl-1H-pyrrol-2-ylmethyl)-3-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of deoxophylloerythroetioporphyrin (DPEP) and three ring homologs by an improved b-bilene methodology

  摘要：

  Deoxophylloerythroetioporphyrin, an important porphyrin molecular fossil from oil shales and petroleum, and three homologs with six-, seven- or eight-membered exocyclic rings have been prepared by a one pot cyclization of b-bilenes with TFA-trimethyl orthoformate in dichloromethane. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01960-1

文献信息

• Porphyrins with exocyclic rings. Part 22: Synthesis of deoxophylloerythroetioporphyrin (DPEP), three ring homologues, and five related nonpolar bacteriopetroporphyrins using a western ring closure and an improved b-bilene methodology
  作者：Timothy D. Lash、Wei Li、Desiree M. Quizon-Colquitt

  DOI：10.1016/j.tet.2007.09.059

  日期：2007.12

  carbaldehydes under mildly acidic conditions. Following deprotection of the terminal ester groups, cyclization with TFA–CH(OMe)3 gave a series of ring homologues of deoxophylloerythroetioporphyrin (DPEP). The b-bilenes generated from the five-membered ring dipyrroles proved to be rather unstable and had to be used directly without purification. Cyclization gave DPEP contaminated with an etioporphyrin by-product

  含有五元碳环的二吡咯中间体很容易从环戊[ b ]吡咯制备，该单元代表在富含机油的沉积物（如油页岩和石油）中发现的DPEP型地卟啉的南半部分。当在温和的酸性条件下与二吡咯甲烷甲醛反应时，具有六元，七元或八元碳环的相关二吡咯显示出b- ene。末端酯基脱保护后，用TFA-CH（OMe）3环化得到一系列的脱氧叶绿体铁卟啉（DPEP）环同系物。在b由五元环二吡咯生成的β-二烯被证明是相当不稳定的，必须不经纯化直接使用。环化产生DPEP并被埃菲卟啉副产物污染，但可以通过快速色谱法将其分离为镍（II）衍生物。与先前报道的方法相比，该方法可产生更高的DPEP产量。另外，该方法可以扩展到相关的卟啉的合成，并且通过这种方法合成了由细菌叶绿素d衍生的一系列五种分子化石。
• Synthesis of deoxophylloerythroetioporphyrin (DPEP) and three ring homologs by an improved b-bilene methodology
  作者：Wei Li、Timothy D. Lash

  DOI：10.1016/s0040-4039(98)01960-1

  日期：1998.11

  Deoxophylloerythroetioporphyrin, an important porphyrin molecular fossil from oil shales and petroleum, and three homologs with six-, seven- or eight-membered exocyclic rings have been prepared by a one pot cyclization of b-bilenes with TFA-trimethyl orthoformate in dichloromethane. (C) 1998 Elsevier Science Ltd. All rights reserved.