anti-Tricyclo<4.2.1.1^2,5>dec-3-en-9-on | 66953-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: anti-Tricyclo<4.2.1.1^2,5>dec-3-en-9-on
• 英文别名: Tricyclo[4.2.1.1(2,5)]dec-3-en-9-one；tricyclo[4.2.1.12,5]dec-3-en-9-one
• CAS: 66953-28-4
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: UYZMLRHSPAUMAN-UHFFFAOYSA-N

物化性质

• 沸点：
  248.4±9.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  anti-Tricyclo<4.2.1.1^2,5>dec-3-en-9-on 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 氯化亚砜 、 硼烷 、 氢气 、 双氧水 作用下， 以 乙醚 、 乙酸甲酯 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 23.0h， 生成 9-endo-(1-hydroxyethyl)-anti-tricyclo<4.2.1.12,5>decane
  参考文献：
  名称：

  Enhanced endo-exo selectivity in the stereochemistry of ketonization of enols. Part 201

  摘要：

  DOI：

  10.1021/jo00210a016
• 作为产物：
  描述：

  cis-2,5-Dibromocyclopentanone 、 环戊二烯 在 PPN(1+)*Cr(CO)4NO(1-) 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到anti-Tricyclo<4.2.1.1^2,5>dec-3-en-9-on
  参考文献：
  名称：

  Attempted Generation of an Observable Ethano-Bridged (Cyclopentyl) Oxyallyl. The Pericyclic Nature of an Oxyallyl-Oxyallyl Dimerization Reaction

  摘要：

  An attempt is made to directly observe an ethano-bridged (cyclopentyl) oxyallyl using a synthetic methodolgy which employs aprotic solvents and homogeneous conditions involving a novel organometallic reagent and which can be carried out at very low temperatures. However, even with preparation temperatures of -120 degrees C, the 2,5-dimethylcyclopentyl oxyallyl is not observable by in situ NMR spectroscopy. Products corresponding to an oxyallyl + oxyallyl dimerization are observed instead. The major dimer is a cis-dioxane compound, and the formation of this suggests a process under pericyclic control. An analysis of the allowed molecular orbital overlaps is presented, and it is concluded that the mutual overlap involves all three terminal orbitals (overlap 2 in Figure 2), with preferential bond formation taking place between carbon(A)-oxygen(B), oxygen(A)-carbon(B), where A and B are the two oxyallyl monomers. The dioxane product represents only one of four possible double-connectivity ways in which two oxyallyl units can be joined (see Figure 1). The initially formed cis-dioxane product is quite labile and is easily transformed in a sequential and stereospecific manner into products representative of two of the other three connectivity modes. The formation of the parent cyclopentyl oxyallyl was also studied under the same reaction conditions. In this case one sees no dimeric products, but the formation of the oxyallyl is indicated because [4 + 3] diene adducts of the putative oxyallyl can be trapped, in; accord with previous work in this area.

  DOI：

  10.1021/ja00086a013

文献信息

• The adamantane rearrangement ofsyn- andanti-Tricyclo[4.2.1.1.12,5] decane. Part II. Rearrangements initiated by regioselective formation of carbocations at C(3) and C(9)
  作者：Marco Brossi、Camille Ganter

  DOI：10.1002/hlca.19880710420

  日期：1988.6.15

  The endo- and exo-alcohols 5–12 of syn-(1) and anti-tricyclo[4.2.1. 12.5]decane (2) were treated with BF3/Et3SiH (ionic hydrogenation) in order to study the behaviour of the corresponding regioselectively generated carbocations at C(3) (a (syn), b (anti)) and C(9) (c (syn), d (anti)). The anti-hydrocarbon 2 is practically the sole product obtained starting with the four 3-alcohols (viaab from 5 and

  的内切-和外切-醇5-12的顺式- （1）和抗-三环[4.2.1。为了研究相应的区域选择性生成的碳正离子在C（3）（a（顺式），b（抗））和C上的行为，用BF 3 / Et 3 SiH（离子加氢）处理了1 2.5个癸烷（2）。（9）（c（syn），d（反））。该抗-烃2实际上唯一的产物获得的起始的四个3-醇（通过一个b从5和6（顺式）和经由b从9和10（反））。在每种情况下四个-9-醇得到的混合物的2-内型，3-内型（ - 3）和2-外，3-外三亚甲基-8,9,10-trinorbornane（4）（通过ç Ë从7和8（syn）并通过d f（11）和（12）（反）），但不涉及烃2，即不涉及1,3-H转变c a和d b。
• Syntheses and PE-Spectroscopic Investigations of 2,6- and 3,5-Bridged 1,4-Dimethylidenecyclohexanes
  作者：Teh-Chang Chou、Holger Lange、Rolf Gleiter、Tibor Gögh、Miroslav Kríž、Max H. Pfenninger、Marian Valentíny、Camille Ganter

  DOI：10.1002/hlca.19950780809

  日期：1995.12.13

  Three 1,4-dimethylidenecyclohexanes, bridged in the 2,6- and 3,5-positions by two ethano (4), one ethano and one propano (5), and two propano bridges (6) have been synthesized. The interaction of the two exocyclic methylidene groups has been investigated by He(I) photoelectron (PE) spectroscopy. It revealed a slightly larger energy difference (0.8 eV) for 4 and 5 as compared to the parent 1,4-dime

  已经合成了由两个乙醇（4），一个乙醇和一个丙烷（5）和两个丙烷桥（6）在2,6-和3,5-位桥接的三个1,4-二甲基亚环己烷。两个外环亚甲基的相互作用已通过He（I）光电子（PE）光谱进行了研究。与母体1,4-二甲基亚环己烷（7）（0.7 eV）相比，它显示出4和5的能量差（0.8 eV）稍大。PE光谱的解释是基于与相关系统的PE数据的比较以及对4-6的半经验计算的结果。
• Froehlisch, Baldur; Joachimi, Roland, Chemische Berichte, 1987, vol. 120, p. 1951 - 1960
  作者：Froehlisch, Baldur、Joachimi, Roland

  DOI：——

  日期：——
• Regioselectivity in cycloadditions of singlet 2-methylenecyclopenta-1,3-diyl species
  作者：Roger K. Siemionko、Jerome A. Berson

  DOI：10.1021/ja00531a032

  日期：1980.5
• Camps, Pelayo; Castane, Joan; Feliz, Miguel, Chemische Berichte, 1989, vol. 122, p. 1313 - 1322
  作者：Camps, Pelayo、Castane, Joan、Feliz, Miguel、Jaime, Carlos、Minguillon, Cristina

  DOI：——

  日期：——