endo-cis-2,3-dimethoxycarbonylnorbornane | 4098-47-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: endo-cis-2,3-dimethoxycarbonylnorbornane
• 英文别名: norbornane-dicarboxylic acid-(2endo.3endo)-dimethyl ester；Norbornan-dicarbonsaeure-(2endo.3endo)-dimethylester；Dimethyl-endo-cis-norbornan-2,3-dicarboxylat；cis-endo-2,3-Dicarbomethoxynorbornan；dimethyl (1S,2S,3R,4R)-bicyclo[2.2.1]heptane-2,3-dicarboxylate
• CAS: 4098-47-9
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: VMPWODPFFNIDSL-SPJNRGJMSA-N

物化性质

• 沸点：
  284.5±13.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  endo-cis-2,3-dimethoxycarbonylnorbornane 在 sodium 作用下， 生成
  参考文献：
  名称：

  Foiled electrocyclic rearrangement of cyclopropyl cations

  摘要：

  DOI：

  10.1021/jo00911a004
• 作为产物：
  描述：

  Dimethyl Bicyclo<2.2.1>hept-2-ene-2,3-dicarboxylate 在 palladium on activated charcoal 3-甲基-1-环己烯 作用下， 以 环己烷 为溶剂， 反应 0.67h， 以93%的产率得到endo-cis-2,3-dimethoxycarbonylnorbornane
  参考文献：
  名称：

  Regioselective catalytic transfer hydrogenation of dimethyl bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate, dimethyl bicyclo[2.2.1]hept-2-ene-2,3-dicarboxylate, and related compounds over palladium on carbon

  摘要：

  DOI：

  10.1021/jo00158a013

文献信息

• Aryl Norbornanes and Analogues via Palladium-Catalyzed Hydroarylation with Arenediazonium Tetrafluoroborates
  作者：Sandro Cacchi、Gabriele Bartoli、Giancarlo Fabrizi、Antonella Goggiamani

  DOI：10.1055/s-2008-1078051

  日期：——

  The palladium-catalyzed hydroarylation of arenediazonium tetrafluoroborates with norbornene derivatives and analogues in the presence of Pd(OAc)2 and i-Pr3SiH in THF affords hydroarylation products containing the added aryl unit in the exo position in good to high yields. The reaction tolerates a variety of useful functional groups and can be performed as a one-pot procedure generating the arenediazonium salt in situ.

  钯催化的芳香重氮四氟硼酸盐与降冰片烯衍生物及其类似物在Pd(OAc)2和i-Pr3SiH存在下于THF中的氢芳基化反应，可以高至很好的产率得到在exo位置含有添加芳基单元的水合芳基产物。该反应容忍多种有用的官能团，并可以采用一锅法进行，即现场生成芳香重氮盐。
• Reductive cleavage of succinic esters. A method for the introduction of acetic acid fragments
  作者：Paul G. Gassman、Xavier Creary

  DOI：10.1039/c39720001214

  日期：——

  Diels–Alder addition of maleic or fumaric esters to 1,3-dienes, followed by catalytic reduction and treatment with sodium in liquid ammonia at –78°, which promotes a solvent dependent reductive cleavage of the carbon–carbon σ bond of the succinic ester fragment, provides a general method for the preparation of derivatives of suberic acid.

  Diels–将马来酸酯或富马酸酯加到1,3-二烯中，然后催化还原并在–78°下用液态氨中的钠进行处理，从而促进了琥珀酸酯的碳-碳σ键的溶剂依赖性还原裂解片段提供了一种制备辛二酸衍生物的通用方法。
• Cobalt‐Catalyzed Hydrogenation and Deuteration Reactions of Bicyclic Alkenes in an Aqueous Environment
  作者：Austin Pounder、Joshua van der Zalm、Aicheng Chen、William Tam

  DOI：10.1002/ejoc.202301306

  日期：2024.3.18

  This study presents cobalt-catalyzed hydrogenation and deuteration of bicyclic alkenes, utilizing H2O and D2O as hydrogen sources with Zn0 or Mn0 reductants. Lewis-acid co-catalysts facilitated reactions and promoted transesterification. Introduction of 1 atm of H2 allowed catalytic metal reductant loading. These processes displayed excellent functional-group tolerance, consistently yielding high-product

  本研究提出了钴催化双环烯烃的氢化和氘化，利用H 2 O 和D 2 O 作为氢源以及Zn 0或Mn 0还原剂。路易斯酸助催化剂促进反应并促进酯交换反应。引入1atm的H 2允许负载催化金属还原剂。这些工艺表现出优异的官能团耐受性，始终保持高产品产量。
• Kohlrausch; Seka, Chemische Berichte, 1936, vol. 69, p. 729,740
  作者：Kohlrausch、Seka

  DOI：——

  日期：——
• Application of electron spin resonance spectroscopy to problems of structure and conformation. XXIV. Aliphatic semidiones. XIX. Polycyclic derivatives of cyclobutanesemidione
  作者：Glen A. Russell、Philip R. Whittle、Robert G. Keske、George Holland、Carol Aubuchon

  DOI：10.1021/ja00760a044

  日期：1972.3