Acetic acid (1R,3aS,4R,7S,7aR)-(3a,4,7,7a-tetrahydro-1H-4,7-methano-inden-1-yl) ester | 123930-78-9

• 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: Acetic acid (1R,3aS,4R,7S,7aR)-(3a,4,7,7a-tetrahydro-1H-4,7-methano-inden-1-yl) ester
• 英文别名: [(1S,2R,3R,6S,7R)-3-tricyclo[5.2.1.02,6]deca-4,8-dienyl] acetate
• CAS: 123930-78-9
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: QXRPTBFQCMXUIE-RNWYCLNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,3aS,4R,7S,7aR)-(3a,4,7,7a-tetrahydro-1H-4,7-methano-inden-1-yl) ester 在 吡啶 、 乙醚 、 mercury(II) diacetate 、 lithium perchlorate 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 2-[(1S,2S,3R,6S,7R)-3-tricyclo[5.2.1.02,6]deca-4,8-dienyl]ethyl benzoate
  参考文献：
  名称：

  Mechanism of Lithium Perchlorate/Diethyl Ether-Catalyzed Rearrangement of α- and β-endo- and -exo-Dicyclopentadienyl Vinyl Ethers:  Use of Deuterium Labeling and a Chiral Probe

  摘要：

  Lithium perchlorate/diethyl ether (LPDE) mediated rearrangement of alpha- and beta-endo-dicyclopentadienyl vinyl ethers 5 and 6 resulted in the formation df the aldehyde 8, indicating that the mechanism is nonconcerted and the recombination of the ion pair occurs at the dissociated stage and not the intimate ion-pair stage. Proof of this came from deuterium-labeling studies and the use of an optically pure starting material. Furthermore, that the ionic intermediate formed must be symmetrical resulting in enantiomeric aldehydes from both normal and allylic attack corresponding to products of formal 1,3 and 3,3 shifts was seen in the chiral analysis of the benzoate derivative of the aldehydes formed from the optically pure vinyl ether.

  DOI：

  10.1021/jo970715t
• 作为产物：
  描述：

  5-exo-hydroxytricyclo[5.2.1.0(2,6)]deca-3,8-diene 在 吡啶 、 乙酸酐 作用下， 生成 Acetic acid (1R,3aS,4R,7S,7aR)-(3a,4,7,7a-tetrahydro-1H-4,7-methano-inden-1-yl) ester
  参考文献：
  名称：

  Preparation and Thermal Rearrangement of Several Dicyclopentadiene Derivatives

  摘要：

  DOI：

  10.1021/ja01569a050

文献信息

• Enantioconvergent route to α-cuparenone from dicyclopentadiene
  作者：Seiichi Takano、Kohei Inomata、Kunio Ogasawara

  DOI：10.1039/c39890000271

  日期：——

  A formal enantioconvergent route to α-cuparenone from dicyclopentadiene has been devised by employing lipase catalysed kinetic hydrolysis as the key step.

  通过采用脂肪酶催化的动力学水解方法，已设计出由双环戊二烯向α-cuparenone转化的正式对映体路线。
• Complex stereochemical course of the mitsunobu “inversion” of allylic alcohols
  作者：Vittorio Farina

  DOI：10.1016/s0040-4039(00)70640-x

  日期：——

  The Mitsunobu esterification reaction of dicyclopentadienols yields mixtures of inversion and retention products. Deuterium labeling demonstrates variable levels of allylic rearrangement.

  二环戊二烯醇的Mitsunobu酯化反应产生了转化产物和保留产物的混合物。氘标记显示出可变水平的烯丙基重排。
• Retro-Diels-Alder Reactions of Masked Cyclopentadienones Catalyzed by Heterogeneous Brønsted Acids
  作者：Anneleen L. W. Demuynck、Pieter Levecque、Aklilu Kidane、David W. Gammon、Eugene Sickle、Pierre A. Jacobs、Dirk E. De Vos、Bert F. Sels

  DOI：10.1002/adsc.201000571

  日期：2010.12.17

  results suggest that retro-Diels–Alder reactions of tricyclodecadienones are catalyzed by Brønsted acids and the high catalytic performance of H-Beta catalysts can be ascribed to the optimal balance between the number of acid sites and their strength as well as to the accessibility of these sites. The methodology was then applied to a series of alkyl derivatives of cyclopentadienylcyclopentenones to provide

  H-Beta沸石在适度的温度和环境压力下，在有活性亲二烯体的情况下，催化一系列环戊二烯环加合物的Diels-Alder逆反应。在筛选环戊二烯酮的环戊二烯加合物的逆Diels-Alder反应中的一系列沸石后，确定了活性催化剂并确定了最佳反应条件。我们的结果表明，三环癸二烯酮的Diels-Alder逆反应是由Brønsted酸催化的，H-Beta催化剂的高催化性能可归因于酸位点数量与它们的强度之间的最佳平衡，以及酸的可及性。这些网站。N-环己基-2-氮杂orborn-5-烯。
• A Stereospecific Approach to<i>cis</i>-<i>anti</i>-<i>cis</i>Triquinanes
  作者：A. Srikrishna、T. Jagadeeshwar Reddy、N. Palani、K. K. Balasubramanian

  DOI：10.1081/scc-120018772

  日期：2003.1.5

  Abstract A methodology for the synthesis of compounds containing the cis-anti-cis fused triquinane system has been developed starting from tricyclo[5.2.1.02,6]deca-4,8-dien-3-(exo)ol 6 involving Ireland ester Claisen rearrangement and intramolecular diazo ketone cyclopropanation reactions as key steps.

  摘要 从涉及爱尔兰酯 Claisen 的三环 [5.2.1.02,6]deca-4,8-​​dien-3-(exo)ol 6 开始，开发了一种合成含有顺-反-顺稠合三喹烷系统的化合物的方法。重排和分子内重氮酮环丙烷化反应是关键步骤。
• Chemoenzymatic approaches to the decahydro-as-indacene cores associated with the spinosyn class of insecticide
  作者：Martin Banwell、David Hockless、Bevyn Jarrott、Brian Kelly、Andrew Knill、Robert Longmore、Gregory Simpson

  DOI：10.1039/b006759h

  日期：——

  The enantiopure dienes 8 and 24, which have been prepared by chemoenzymatic methods, engage in Diels–Alder cycloaddition reactions with maleic and citraconic anhydride to give adducts (e.g.25–27) embodying the ABC-ring system associated with spinosyns A (1) and D (2).

  通过化学酶法制备的不纯对映体二烯 8 和 24 与马来酸酐和柠檬酸酐发生 Diels-Alder 环加成反应，生成体现 ABC 环系统的加合物（如 25-27），该系统与旋光子炔 A (1) 和 D (2) 相关。