benzyl 5'-t-butoxycarbonyl-3,4'-diethyl-4,3'-dimethyl-2,2'-dipyrrimethane-5-carboxylate | 52459-98-0

• 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 5'-t-butoxycarbonyl-3,4'-diethyl-4,3'-dimethyl-2,2'-dipyrrimethane-5-carboxylate
• 英文别名: 5-benzyl 5'-t-butyl 3,4'-diethyl-3',4-dimethylpyrromethane-5,5'-dicarboxylate；benzyl 5'-t-butoxycarbonyl-3,4'-diethyl-3',4-dimethyldipyrrylmethane-5-carboxylate；benzyl tert-butyl pyrromethane-5,5'-dicarboxylate；benzyl 5'-t-butoxycarbonyl-3,4'-diethyl-4,3'-dimethyl-2,2'-dipyrrylmethane-5-carboxylate；3,4'-diethyl-4,3'-dimethyl-1H,1'H-5,5'-methanediyl-bis-pyrrole-2-carboxylic acid 2'-benzyl ester 2-tert-butyl ester；Benzyl 5'-(tert-butoxycarbonyl)-3,4'-diethyl-3',4-dimethylpyrromethane-5-carboxylate；tert-butyl 3-ethyl-5-[(3-ethyl-4-methyl-5-phenylmethoxycarbonyl-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrole-2-carboxylate
• CAS: 52459-98-0
• 化学式: C₂₈H₃₆N₂O₄
• 分子量: 464.605
• InChiKey: VVNRKEBSKLDIGY-UHFFFAOYSA-N

物化性质

• 熔点：
  132-134 °C
• 沸点：
  627.6±55.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 5'-t-butoxycarbonyl-3,4'-diethyl-4,3'-dimethyl-2,2'-dipyrrimethane-5-carboxylate 在 palladium on activated charcoal 氢溴酸 、 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 丙酮 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 9.67h， 生成 1,3,6-Triethyl-2,4,5-trimethyltripyrrene-b-1',6'-dicarboxylic Acid Hydrobromide
  参考文献：
  名称：

  Peripheral mercuration of metalloporphyrins: novel syntheses of deoxophylloerythroetioporphyrin and deoxophylloerythrin methyl ester

  摘要：

  DOI：

  10.1021/jo00198a006
• 作为产物：
  描述：

  tert-butyl 3-ethyl-5-iodo-4-methylpyrrole-2-carboxylate 在 platinum(IV) oxide 氢气 、 sodium acetate 、 对甲苯磺酸 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 benzyl 5'-t-butoxycarbonyl-3,4'-diethyl-4,3'-dimethyl-2,2'-dipyrrimethane-5-carboxylate
  参考文献：
  名称：

  Clewlow, Paul J.; Jackson, Anthony H., Journal of the Chemical Society. Perkin transactions I, 1990, # 7, p. 1925 - 1936

  摘要：

  DOI：

文献信息

• Total synthesis of the porphyrin mineral abelsonite and related petroporphyrins with five-membered exocyclic rings
  作者：Bo Zhang、Timothy D. Lash

  DOI：10.1016/j.tetlet.2003.08.007

  日期：2003.9

  A reliable synthesis of porphyrins with five-membered exocyclic rings from b-bilenes has been developed. This methodology has been applied to the first total synthesis of the porphyrin mineral abelsonite, as well as the widespread petroporphyrin deoxophylloerythroetioporphyrin (DPEP) and its 3-desethyl analogue.

  已开发了由b-比林可靠合成具有五元环外环的卟啉的方法。该方法已应用于卟啉矿物亚硒酸钠的首次全合成，以及广泛的石油卟啉脱氧叶绿体铁卟啉（DPEP）及其3-去乙基​​类似物。
• Synthesis of the C30 desethylaetioporphyrin from petroleum
  作者：Paul J. Clewlow、Anthony H. Jackson、Ian Roberts

  DOI：10.1039/c39850000724

  日期：——

  The four desethyl analogues of aetioporphyrin-III have been synthesised by the biladiene route; h.p.l.c. comparisons showed that the desethylaetioporphyrin obtained from petroleum is the C-ring isomer (3c).

  通过双二烯途径合成了四倍的卟啉-III的去乙基类似物。hplc比较显示，从石油中获得的去乙基乙酰卟啉为C环异构体（3c）。
• Bile pigment studies—VI
  作者：Kevin M. Smith、Dharma Kishore

  DOI：10.1016/s0040-4020(01)88697-x

  日期：——

  Owing to symmetry limitations inherent in the a,c-biladiene route, that through b-bilenes is shown to be more generally effective for the synthesis of biliverdins. The key step in the transformation of the biladiene or bilene into biliverdin involves treatment with bromine in trifluoroacetic acid, and this affords biliverdin in high yield. The route is proposed to proceed through a 1,19-dibromo-a,b

  讨论了由单吡咯和完整的金属卟啉和金属氯霉素的环裂解合成各种哺乳动物和藻类胆色素模型的方法。etiobiliverdin IV的先前报道的合成γ（6从5-溴-5'- bromomethyldipyrrylmethene氢溴酸盐（的自缩合）5）被修改通过1,19-二-得起biliverdins一种新型，高效和一般路线叔丁氧基羰基一，ç -biladienes或- b -bilenes。由于a，c-二苯二烯路线固有的对称性限制，即通过b已显示出-胆甾醇对biliverdins的合成更普遍有效。将胆二烯或胆二烯转化为胆绿素的关键步骤涉及在三氟乙酸中用溴处理，这可以高产率得到胆绿素。路线提出通过1,19-二溴进行一个，b，c ^ -bilitriene然后1,19-二- （三氟乙酰氧基） -一个，b，c ^ -bilitriene，虽然这些中间体不分离。
• Clezy, Peter S.; Fookes, Christopher J. R.; Prashar, Jognandan K., Australian Journal of Chemistry, 1989, vol. 42, # 6, p. 775 - 786
  作者：Clezy, Peter S.、Fookes, Christopher J. R.、Prashar, Jognandan K.

  DOI：——

  日期：——
• Total synthesis of cyclopentenoporphyrins of sedimentary origin: deoxophylloerythroetioporphyrin, chlorophyll c fossils and related compounds.
  作者：Claude Bauder、Rubén Ocampo、Henry J. Callot

  DOI：10.1016/s0040-4020(01)90123-1

  日期：1992.1

  This article describes the total synthesis of seven porphyrins, fossils of chlorophyll derivatives, isolated from sedimentary sources and possess five-membered rings fused to the porphyrin nucleus, this additional ring being placed between positions 13,15 or 15,17. This ring was built from vinyl, hydroxyethyl or isopropenyl groups under strong acidic conditions.