(1R^*,7S^*)-Tricyclo<6.3.0.0^3,7>undec-1(8)-en-2-one | 58866-23-2

• 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: (1R^*,7S^*)-Tricyclo<6.3.0.0^3,7>undec-1(8)-en-2-one
• 英文别名: Tricyclo<6.3.0.0^3,7>undec-Δ^3,7-en-2-one；cis-Tricyclo<6.3.0.0^3,7>undec-1(8)-en-2-one；(3aR,7aS)-1,2,3,3a,4,5,6,7a-octahydrocyclopenta[a]pentalen-7-one
• CAS: 58866-23-2；108686-36-8；138622-56-7
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: MHJHXQGYYHAJSC-CBAPKCEASA-N

物化性质

• 沸点：
  293.8±7.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  cyclopentane-cis-1,2-dicarboxylic acid anhydride 在 甲烷磺酸 、 phosphorus pentoxide 作用下， 以 四氢呋喃 为溶剂， 反应 34.0h， 生成 (1R^*,7S^*)-Tricyclo<6.3.0.0^3,7>undec-1(8)-en-2-one
  参考文献：
  名称：

  线性稠合聚喹啉合成的一般方法

  摘要：

  已经开发出一种方法，该方法涉及通过1，4-二溴镁砂丁烷对琥珀酸衍生物的作用进行螺环化，然后使用P 2 O 5 -CH 3 SO 3 H试剂将螺内酯环化，以合成聚喹烷。通过使用双环[2.2.1]庚烷羧酸作为螺内酯的前体，已合成了三喹烷[8]和五喹烷[19]。

  DOI：

  10.1016/s0040-4020(01)89030-x

文献信息

• Construction of aryl-substituted triquinanes through the interrupted Nazarov reaction
  作者：Curtis J. Rieder、Ryan J. Fradette、F. G. West

  DOI：10.1039/b800800k

  日期：——

  The first examples of intermolecular trapping of Nazarov cyclopentenyl cation intermediates by simple arenes to furnish alpha-arylcyclopentanones are described.

  描述了通过简单的芳烃分子间捕获Nazarov环戊烯基阳离子中间体以提供α-芳基环戊烯酮的第一个实例。
• Heteroaromatic Trapping of Tricyclic 2-Oxidocyclopentenyl Cations: A Surprisingly Efficient Example of Intermolecular Interrupted Nazarov Reaction
  作者：Frederick G. West、Curtis J. Rieder、Ryan J. Fradette

  DOI：10.3987/com-09-s(s)132

  日期：——

  Bis(cycloalkenyl) ketones 2a and 2f underwent Nazarov cyclization and intermolecular trapping by electrophilic aromatic substitution with furans, thiophenes, pyrroles, indoles and dimethoxybenzene. Only the cis-anti-cis diastereomer was isolated with dicyclopentenyl ketone 2a, whereas a mixture of diastereomers was seen with 2f (albeit with complete regioselectivity). Comparable interrupted Nazarov trapping was not seen with acyclic dienones 2b-e, indicating the possible involvement of conformation effects in the polycyclic intermediates derived from 2a and 2f.
• Reactions of enaminones with 1-nitroolefins. Scope and limitations of a polyquinane synthesis
  作者：John W. Huffman、Melanie M. Cooper、Barnabe B. Miburo、William T. Pennington

  DOI：10.1016/s0040-4020(01)80490-7

  日期：1992.1

  The reaction of several 2-aminocyclohex-2-en-1-ones with cyclic nitroolefins has been explored as a possible synthetic approach to polyquinanes. 2-Pyrrolidino, 2-piperidino and 2-morpholinocyclohex-2-en-1-one react with 1-nitrocyclopentene to provide substituted triquinanes. Reactions involving 5,5-dimethyl-2-morpholinocyclohex-2-en-1-one were unsuccessful as were those using 4,4-dimethyl-1-nitrocyclopentene. 5-Methyl-2-morpholinocyclohex-2-en-1-one and 1-nitrocyclopentene provide the corresponding triquinane, plus a by-product in which the amino substituent has been lost. The reactions of other selected nitroolefins have been carried out, and the products are described. The results of these reactions are rationalized in terms of an inverse electron demand Diels-Alder reaction to afford an intermediate oxazine N-oxide, which then undergoes further transformations to afford the observed products.
• New easy access to cyclopentanoid structures
  作者：Brigitte Jamart-Grégoire、Nicolas Brosse、Sandra Ianelli、Mario Nardelli、Paul Caubère

  DOI：10.1016/0040-4039(91)80691-x

  日期：1991.6

  We describe new easy synthesis of functionalized di and tricyclic cyclopentane containing derivatives. The stereochemistries of the ring junction are well defined. The starting material tricyclic methylene cyclobutanols are easily obtained on large scale from inexpensive substrates.
• Easy access to cyclopentanoid structures. 1. Preparation and transposition of tricyclo[m.n.0.02,m+1]alca-2,3,m + 2-triol derivatives
  作者：Brigitte Jamart-Gregoire、Nicolas Brosse、Sandra Ianelli、Mario Nardelli、Paul Caubere

  DOI：10.1021/jo00069a016

  日期：1993.8

  Methylenecyclobutanols 1, conveniently obtained by 1,2-cycladiene condensation of ketone enolates, were used as starting materials for the easy preparation of polycyclic cyclopentane derivatives. Thus, the transposition and transposition-elimination of triol derivatives 3, 5, and 6 led to the synthesis of a series of polycyclic cyclopentan- or cyclopentenones. The stereochemistries of the transpositions were studied and mechanisms were proposed.