dibenzyl 2,3-pentadienedioate | 214116-47-9

• 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: dibenzyl 2,3-pentadienedioate
• 英文别名: Dibenzyl penta-2,3-dienedioate
• CAS: 214116-47-9
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: NEJUZSGJQQOQMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dibenzyl 2,3-pentadienedioate 、 4-乙氧基-3-(1-甲氧基乙烯基)-1-甲基-1,5-二氢-2H-吡咯-2-酮 以25%的产率得到5-Benzyloxycarbonylmethyl-7-methoxy-2-methyl-1-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid benzyl ester
  参考文献：
  名称：

  针对内酰胺霉素的全合成的研究：通过直接的分子内催化控制醌的环加成感。

  摘要：

  DOI：

  10.1002/anie.200352591
• 作为产物：
  描述：

  dibenzyl 1,3-acetonedicarboxylate 在 2-chloro-1,3-dimethyl imidazolium chloride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以70%的产率得到dibenzyl 2,3-pentadienedioate
  参考文献：
  名称：

  DMC合成1,3-二羧酸Allene的新方法和串联环化成吡咯烷核生物碱骨架的新方法

  摘要：

  通过使用DMC作为脱水试剂，高产率地从1,3-二羧酸丙酮中合成了1,3-二羧酸Allene-1。此过程开辟了一条新的快速途径，即通过迈克尔加成反应和新颖的串联环化反应，从1,3-二羧酸二甲酯和双（2-氯乙基）胺合成吡咯烷核生物碱的1-azabicyclo [3.3.0]辛烷骨架。

  DOI：

  10.1016/s0040-4039(98)01344-6

文献信息

• A new synthetic method for allene-1,3-dicarboxylates using DMC and a novel tandem cyclization to a pyrrolizidine alkaloid skeleton
  作者：Manabu Node、Toshio Fujiwara、Shogo Ichihashi、Kiyoharu Nishide

  DOI：10.1016/s0040-4039(98)01344-6

  日期：1998.8

  one-step synthesis of allene-1,3-dicarboxylates from acetone-1,3-dicarboxylates in high yields was developed by the use of DMC as a dehydrating reagent. This process opened a new expeditious route to a 1-azabicyclo[3.3.0]octane skeleton of pyrrolizidine alkaloids from dimethyl acetone-1,3-dicarboxylate and bis(2-chloroethyl)amine via a Michael addition and a novel tandem cyclization.

  通过使用DMC作为脱水试剂，高产率地从1,3-二羧酸丙酮中合成了1,3-二羧酸Allene-1。此过程开辟了一条新的快速途径，即通过迈克尔加成反应和新颖的串联环化反应，从1,3-二羧酸二甲酯和双（2-氯乙基）胺合成吡咯烷核生物碱的1-azabicyclo [3.3.0]辛烷骨架。
• A practical improvement of crystallization-induced asymmetric transformation of allene-1,3-dicarboxylates
  作者：Takahiro Katoh、Chie Noguchi、Hiroyuki Kimura、Toshio Fujiwara、Shogo Ichihashi、Kiyoharu Nishide、Tetsuya Kajimoto、Manabu Node

  DOI：10.1016/j.tetasy.2006.11.004

  日期：2006.11

  Enantiomerically pure allene-1,3-dicarboxylates were easily synthesized by using epimerization-crystallization of dissymmetric allene compounds, which were prepared from acetone-1,3-dicarboxylates and naturally abundant chiral alcohols, that is, (-)and (+)-menthols, borneol, and isoborneol. After scrutinizing the crystallization of several allene-1,3-dicarboxylates in the presence of triethylamine, it was found that allene-1,3-dicarboxylate carrying bornyl groups was the most easily prepared as a single isomer because of it having suitable solubility to be crystallized in hexane at 0 degrees C to room temperature. Diels-Alder reaction of the enantiomerically pure allene-1,3-dicarboxylates and cyclic dienes, such as N-Boc-pyrrole and cyclopentadiene, afforded endo-adducts having the same configurations at two newly generated stereogenic centers. (c) 2006 Elsevier Ltd. All rights reserved.
• Studies Directed toward the Total Synthesis of Lactonamycin: Control of the Sense of Cycloaddition of a Quinone through Directed Intramolecular Catalysis
  作者：Christopher D. Cox、Tony Siu、Samuel J. Danishefsky

  DOI：10.1002/anie.200352591

  日期：2003.11.24