D-(+)-methyl 3-camphocarboxylate | 111322-84-0

• 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: D-(+)-methyl 3-camphocarboxylate
• 英文别名: (1R)-4,7,7-trimethyl-3-oxo-norbornane-2ξ-carboxylic acid methyl ester；(1R)-4,7,7-Trimethyl-3-oxo-norbornan-2ξ-carbonsaeure-methylester；(1R)-3-Oxo-4.7.7-trimethyl-norbornan-carbonsaeure-(2ξ)-methylester；Camphocarbonsaeure-methylester；methyl (1R,4R)-4,7,7-trimethyl-3-oxobicyclo[2.2.1]heptane-2-carboxylate
• CAS: 111322-84-0
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: RZZJYPZBDOCMEC-RLWSYNJZSA-N

物化性质

• 沸点：
  267.0±23.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D-(+)-methyl 3-camphocarboxylate 在 sodium methylate 作用下， 生成 (1R)-3-ethyl-1,7,7-trimethyl-norbornan-2-one
  参考文献：
  名称：

  The lithospheric mantle beneath the Kerguelen Islands (Indian Ocean): petrological and petrophysical characteristics of mantle mafic rock types and correlation with seismic profiles

  摘要：

  Deep-seated meta-igneous xenoliths brought to the surface by alkali basaltic magmas from the Kerguelen Islands reveal that basaltic magmas have intruded the upper mantle throughout their geological evolution. These xenoliths record volcanic activity associated with their early South East Indian Ridge location and subsequent translation to an intraplate setting over the Kerguelen Plume. The meta-igneous xenoliths sample two distinctive geochemical episodes: one is tholeiitic transitional and one is alkali basaltic. Geothermobarometry calculations provide a spatial context for the rock type sequence sampled and for interpreting petrophysical data. The garnet granulites equilibrated over a pressure range of 1.15 to 1.35 GPa and the garnet pyroxenite at 1.8 GPa. Ultrasonic measurements of compressional wave speed V-P have been carried out at pressures up to I GPa, and densities measured for representative samples of meta-igneous xenoliths and for a harzburgite that represents the peridotitic mantle. V-P and density have also been calculated using modal proportions of minerals and appropriate elastic properties for the constituent minerals. Calculated and measured V-P agree well for rock types with microstructures not complicated by kelyphitic breakdown of garnet and/or pervasive grain-boundary cracking. Pyroxene granulites have measured and calculated V-P within the range 7.37-7.52 km/s; calculated velocities for the garnet granulites and pyroxenites range from 7.69 to 7.99 km/s. whereas measured and calculated V-P for a mantle harzburgite Lire 8.45 and 8.29 km/s respectively. The Seismic Structure observed beneath the Kerguelen Islands can be explained by (1) a mixture or underplated pyroxene granulites and ultramafic rocks responsible for the 2-3 km low velocity transitional zone below the oceanic layer 3, (2) varying proportions of granulites and pyroxenites in different regions within the upper mantle producing the lateral heterogeneities, and (3) intercalation of the granulites and pyroxenites throughout the entire upper Mantle Column, along with elevated temperatures, accounting for the relatively low mantle velocities (7.70-7.95 km/s).

  DOI：

  10.1007/s004100100289
• 作为产物：
  描述：

  白樟油 在 乙醚 、 氨 、 sodium amide 作用下， 生成 D-(+)-methyl 3-camphocarboxylate
  参考文献：
  名称：

  The Carbethoxylation and Carbonation of Ketones Using Sodium Amide. Synthesis of β-Keto Esters¹

  摘要：

  DOI：

  10.1021/ja01238a045

文献信息

• Reinvestigation of the Reactions of Camphorketene:  Structural Evidence for Pseudopericyclic Pathways¹
  作者：William W. Shumway、N. Kent Dalley、David M. Birney

  DOI：10.1021/jo015698t

  日期：2001.8.1

  transition structure (10) for the dimerization of s-Z-formylketene (8) is consistent with this mechanism. Trapping of 2 with alcohols shows selectivity comparable to other alpha-oxoketenes. The lack of reaction of 2 with benzaldehyde and the lack of enol tautomers in camphoric acid derivatives is attributed to angle strain in the bicyclic camphor moiety.

  樟脑烯酮（2）的二聚体（3和4）的立体化学已经确定。3、20和相关化合物的晶体结构显示出基态畸变，这被解释为预形成了平面，假周环过渡态，以进行逆向环加成反应形成α-氧杂环丁烯。B3LYP / 6-31G *用于sZ-甲酰基乙烯酮（8）二聚化的过渡结构（10）的优化几何形状与该机理一致。用醇捕集2的选择性与其他α-氧杂环丁烷相当。樟脑酸衍生物中2与苯甲醛的反应不足和烯醇互变异构体的缺乏归因于双环樟脑部分的角度应变。
• Bruehl, Chemische Berichte, 1902, vol. 35, p. 3624
  作者：Bruehl

  DOI：——

  日期：——
• Minguin, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1891, vol. 112, p. 1371
  作者：Minguin

  DOI：——

  日期：——
• Minguin, Annales de Chimie (Cachan, France), 1894, vol. <7> 2, p. 281
  作者：Minguin

  DOI：——

  日期：——
• Bruehl, Chemische Berichte, 1903, vol. 36, p. 4286
  作者：Bruehl

  DOI：——

  日期：——