methyl 2-methyl-1,3-dioxo-1,2,3,4,5,6,7,8-octahydro-3a,7,8-(epiprop[2]ene[1,1,3]triyl)-5,8a-methanocyclohepta[c]pyrrole-7-carboxylate | 1415923-69-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-methyl-1,3-dioxo-1,2,3,4,5,6,7,8-octahydro-3a,7,8-(epiprop[2]ene[1,1,3]triyl)-5,8a-methanocyclohepta[c]pyrrole-7-carboxylate
• 英文别名: Methyl 12-methyl-11,13-dioxo-12-azapentacyclo[6.5.1.01,10.02,6.05,10]tetradec-3-ene-6-carboxylate
• CAS: 1415923-69-1
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: GQMBUKFJXVHFOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl (1RS)-1-[(2-methyl-1,3-dioxo-1,2,3,4,5,6-hexahydrocyclopenta[c]pyrrol-5-yl)methyl]-2-oxocyclopentanecarboxylate 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 palladium diacetate 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 92.5h， 生成 methyl 2-methyl-1,3-dioxo-1,2,3,4,5,6,7,8-octahydro-3a,7,8-(epiprop[2]ene[1,1,3]triyl)-5,8a-methanocyclohepta[c]pyrrole-7-carboxylate
  参考文献：
  名称：

  An Entry to Functionalized 2,8-Ethanonoradamantane Derivatives

  摘要：

  The synthesis of a functionalized derivative containing the 2,8-ethanonoradamantane carbocyclic skeleton, whose key-step consists of an intramolecular Diels-Alder reaction, is described. Chemoselective reduction of an intermediate enone required protection of the maleimide function through their Diets-Alder adducts with furan.

  DOI：

  10.1021/jo302398c

文献信息

• Improved synthesis of a functionalized 2,8-ethanonoradamantane derivative
  作者：Pelayo Camps、Tània Gómez、Ane Otermin

  DOI：10.1016/j.tet.2014.05.096

  日期：2014.8

  An improved preparation of a functionalized 2,8-ethanonoradamantane derivative, which avoids two protection/deprotection steps while deprotection of a benzyloxymethyl protecting group takes place during an acid-catalyzed dehydration, is described. Altogether the synthesis has been reduced in five steps (from 16 to 11 steps) with an increase in the global yield from 5.8 to 7.2%. (C) 2014 Elsevier Ltd. All rights reserved.