(1R,2S,6R,7S)-tricyclo<5.2.1.0^2.6>dec-8-ene-2.6-dicarboxylic anhydride | 95924-50-8

• 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: (1R,2S,6R,7S)-tricyclo<5.2.1.0^2.6>dec-8-ene-2.6-dicarboxylic anhydride
• 英文别名: (1R,2S,6R,7S)-tricyclo[5.2.1.0^2.6]dec-8-ene-2.6-dicarboxylic anhydride；(1S,2R,5S,6R)-8-oxatetracyclo[4.3.3.12,5.01,6]tridec-3-ene-7,9-dione
• CAS: 95924-50-8
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: DWTVIISKEVDPDI-IVQVNHIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (1R,2S,6R,7S)-tricyclo<5.2.1.0^2.6>dec-8-ene-2.6-dicarboxylic anhydride 在 lithium aluminium tetrahydride 、 N-dimethyl-4-pyridine 、 potassium hydrogencarbonate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Guest/Host Relationships in the Synthesis of the Novel Cage-Based Zeolites SSZ-35, SSZ-36, and SSZ-39

  摘要：

  Here, we report the synthesis and structure of three high-silica molecular sieves, SSZ-35, SSZ-36, and SSZ-39, that are prepared from a library of 37 different cyclic and polycyclic quaternized amine molecules that are used as structure-directing agents (SDAs). The size and shape of the quaternized amine molecules are purposely designed in order to obtain novel zeolite structures, and the synthesis of these molecules is presented. The selectivity for the three molecular sieve phases is found to depend on both the SDA and the degree of heteroatom lattice substitution of Al3+ or B3+ in the silicate framework. Molecular modeling is utilized to probe the effects of the nonbonded SDA/zeolite-framework interaction energy on the selectivity for the observed molecular sieve phase. The Rietveld refinement of the powder X-ray data confirms the structure of the SSZ-39 zeolite to be isomorphous with the aluminophosphate molecular sieve, SAPO-LS (AEI). The structure of SSZ-36 is found to possess a range of fault probabilities between the two-dimensional channel system, end-member polymorphs, ITQ-3 and RUB-13 (International Zeolite Association Codes ITE and RTH, respectively). The SSZ-35 structure is reported to contain a one-dimensional pore system possessing stacked cages circumscribed by alternating rings of 10 and 18 tetrahedral atoms (10- and 18-membered rings).

  DOI：

  10.1021/ja990722u
• 作为产物：
  描述：

  1-环戊烯-1,2-二羧酸酐 、 环戊二烯 在 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以90%的产率得到(1R,2S,6R,7S)-tricyclo<5.2.1.0^2.6>dec-8-ene-2.6-dicarboxylic anhydride
  参考文献：
  名称：

  Ghosh, Subrata; Roy, Supti Saha; Bhattacharya, Atashi, Synthetic Communications, 1989, vol. 19, # 18, p. 3191 - 3198

  摘要：

  DOI：

文献信息

• A study of the diels-alder reaction of 3-oxabicyclo[3.3.0]oct-1(5)-ene-2,4-dione with cyclopentadiene and some related dienes
  作者：P. Camps、J. Castañé、M. Feliz、M. Figueredo

  DOI：10.1016/s0040-4020(01)91277-3

  日期：1984.1

  stereoselectivity in the last reaction. Steric factors seem to be responsible for the absence of reaction between 2 and 4. The analysis of the 13C NMR spectra of these adducts and some derived compounds confirms the tentative configuration assignment carried out on the basis of PMR data. Also, the synthesis of dimethyl(1R,2S,6R,7S)-10-oxotricy-clo [5.2.1.02.6]decane2,6-decarboxylate, 1, from the endo-adduct

  3-氧杂双环[3.3.0]辛-1-（5）烯-2,4-二酮2与环戊二烯3、5,5-二乙氧基环戊二烯4和6,6-二甲基富勒烯5的反应是研究过。的反应2倍3的产率的预期内切-adduct，而反应2和5给出的混合物中内切-和外切-adducts其比例是略微依赖于反应条件。在过渡态下导致外向的有吸引力的静电相互作用-加合物可以解释在最后的反应中没有内在立体选择性。立体因素似乎是造成2和4之间没有反应的原因。这些加合物和某些衍生化合物的13 C NMR光谱分析证实了基于PMR数据进行的暂定构型分配。另外，描述了由2和5的反应的内加成物合成二甲基（1R，2S，6R，7S）-10-氧合-闭[5.2.1.0 2.6 ]癸烷2，6-脱羧酯1。
• An expeditious approach to highly functionalized angularly fused 5–5–n ring systems through ring opening–ring closing metathesis of norbornene derivatives
  作者：Ritabrata Datta、Sritama Bose、Pipaliya B. Viththlbhai、Subrata Ghosh

  DOI：10.1016/j.tetlet.2014.04.091

  日期：2014.6

  A new general route for the construction of angularly arrayed 5–5–n ring systems is described using tandem ring opening–ring closing metathesis of appropriately designed norbornene derivatives as the key step.

  使用适当设计的降冰片烯衍生物的串联开环-闭环复分解法作为关键步骤，描述了构造成角度排列的5–5– n环系统的新通用路线。
• Reductive cleavage of carboncarbon bond. A facile route to bridged eight membered rings related to taxanes
  作者：Ghosh Subrata、Karpha Atashi、Saha Goutam、Patra Debasis

  DOI：10.1016/s0040-4039(00)74212-2

  日期：1992.4

  1,4-Dimesylate embodied in strained polycyclic systems 2,7,10 undergoes facile reductive CC bond cleavage to bridged eight membered rings 4, 8, 11 while the less strained 14 gives reduced product 15.

  体现在应变多环系统2,7,10中的1,4-二甲磺酸酯经历了容易的还原性CC键裂解，形成桥连的八元环4、8、11 ，而应变较小的14则生成的产物15减少。
• Ghosh, Subrata; Sarkar, Subrata; Saha, Goutam, Journal of the Chemical Society. Perkin transactions I, 1993, # 19, p. 2281 - 2286
  作者：Ghosh, Subrata、Sarkar, Subrata、Saha, Goutam

  DOI：——

  日期：——
• Strain assisted carbon-carbon bond cleavage via carbon centred radical. A facile route to bridged eight membered rings
  作者：Subrata Sarkar、Subrata Ghosh

  DOI：10.1016/s0040-4039(00)60501-4

  日期：1993.4

  Tributyltin hydride reaction of the tricyclo[5.2.1.0(2, 6)]decenes 3, 11, 15 bearing the 1,4-halo carbonyl system has been shown to involve C-C bond cleavage as the major reaction path leading to bridged eight membered rings in contrast to reduction of the carbon-halogen bond in 7.