benzyl 4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate | 143064-84-0

• 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 4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
• 英文别名: benzyl 3:4-butanopyrrole-2-carboxylate
• CAS: 143064-84-0
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: QMPUSVUPARNHNM-UHFFFAOYSA-N

物化性质

• 沸点：
  469.5±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl 4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate 在 palladium on activated charcoal 氢气 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 3-formyl-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid
  参考文献：
  名称：

  官能化的2,2'-联吡咯的合成改进

  摘要：

  一系列2,2'-联吡咯已使用基于各种2碘吡咯的Pd（0）催化均偶联的改进合成方法进行了有效合成。这种新的合成方法是在室温和水存在下进行的。诸如甲酰基，酯和腈的官能团能够在这些反应条件下存活。发现溶剂在该反应中起重要作用。

  DOI：

  10.1021/jo701310k
• 作为产物：
  描述：

  甘氨酸苄酯对甲苯磺酸盐 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 benzyl 4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
  参考文献：
  名称：

  Synthesis of Pyrroles from Benzyl Isocyanoacetate

  摘要：

  在碱催化下，异氰基乙酸苄酯与δ-乙酰氧基硝基化合物或硝基烯在回流的四氢呋喃中缩合，制备出了收率极高的 5-未取代吡咯-2-羧酸苄酯。 这些吡咯产物是合成卟啉和相关化合物的重要中间体。

  DOI：

  10.1055/s-1994-25431

文献信息

• 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.
• Porphyrins with exocyclic rings. 2. Synthesis of geochemically significant tetrahydrobenzoporphyrins from 4,5,6,7-tetrahydro-2H-isoindoles
  作者：Donald A. May、Timothy D. Lash

  DOI：10.1021/jo00044a013

  日期：1992.8

  Benzo- and tetrahydrobenzoporphyrins are widespread constituents of oil shales and petroleum. Although the origins of these materials are not known, a case is made for divinylchlorophyll a, a widespread pigment in marine algae, being the precursor to many of these geoporphyrins. Total syntheses of four tetrahydrobenzoporphyrins related to etioporphyrin III are described. Tetrahydroisoindoles were prepared by condensation of isocyanoacetates with 1-nitrocyclohexene in the presence of DBU or by reaction of aminomalonates with 2-formylcyclohexanone. Condensation of 3-unsubstituted 4,5,6,7-tetrahydro-2H-isoindoles 23c and 23d with (acetoxymethyl)pyrroles in the presence of Montmorillonite clay gave dipyrrylmethanes 28a and 36a in excellent yield. Hydrogenolysis of the benzyl esters and subsequent acid-catalyzed condensation with pyrrole aldehydes 37a and/or 37b gave a series of a,c-biladiene dihydrobromides. Copper(II) mediated cyclization of the a,c-biladienes 32, 33, 35, and 38, followed by demetallation with 15% sulfuric acid-trifluoroacetic acid, gave four isomeric tetrahydrobenzoporphyrins 10-13 in unusually high yield. This work provides a general route for the synthesis of these important porphyrin molecular fossils.
• Synthesis of Pyrroles from Benzyl Isocyanoacetate
  作者：Timothy D. Lash、John R. Bellettini、Jolie A. Bastian、Kendall B. Couch

  DOI：10.1055/s-1994-25431

  日期：——

  Benzyl esters of 5-unsubstituted pyrrole-2-carboxylic acids were prepared in excellent yields by the base-catalyzed condensation of benzyl isocyanoacetate with α-acetoxynitro compounds, or nitroalkenes,in refluxing tetrahydrofuran. These pyrrolic products are important intermediates in the synthesis of porphyrins and related compounds.

  在碱催化下，异氰基乙酸苄酯与δ-乙酰氧基硝基化合物或硝基烯在回流的四氢呋喃中缩合，制备出了收率极高的 5-未取代吡咯-2-羧酸苄酯。 这些吡咯产物是合成卟啉和相关化合物的重要中间体。
• Improved Synthesis of Functionalized 2,2‘-Bipyrroles
  作者：Lijuan Jiao、Erhong Hao、M. Graça H. Vicente、Kevin M. Smith

  DOI：10.1021/jo701310k

  日期：2007.10.1

  A series of 2,2‘-bipyrroles has been efficiently synthesized using an improved synthetic approach based on Pd(0)-catalyzed homocoupling of various 2-iodopyrroles. This new synthetic approach takes place at room temperature and in the presence of water. Functional groups such as formyl, ester, and nitrile are able to survive these reaction conditions. Solvents are found to play an important role in

  一系列2,2'-联吡咯已使用基于各种2碘吡咯的Pd（0）催化均偶联的改进合成方法进行了有效合成。这种新的合成方法是在室温和水存在下进行的。诸如甲酰基，酯和腈的官能团能够在这些反应条件下存活。发现溶剂在该反应中起重要作用。