(1R,2S,3R,4S)-3-Acetyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde | 220191-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3R,4S)-3-Acetyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde
• 英文别名: Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-acetyl-, [1R-(endo,endo)]-(9CI)；(1R,2S,3R,4S)-3-acetylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde
• CAS: 220191-57-1
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: PIGVZYHJMXOEQI-QCLAVDOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4S)-3-Acetyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,2S,6R,7S)-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one
  参考文献：
  名称：

  Lipase–triethylamine-mediated dynamic transesterification of a tricyclic acyloin having a latent meso-structure: a new route to optically pure oxodicyclopentadiene

  摘要：

  在脂肪酶三乙胺介导的动力学酯交换反应条件下，通过瞬时形成中烯二醇异构体，动态解析了外消旋三环丙烯(±)-内向-3-羟基三环[4.2.1.0 2,5 ]壬-7-烯-4-酮，得到了单一手性乙酸酯(-)-内向-3-乙酰氧基三环[4.2.1.0 2,5 ]非-7-烯-4-酮，作为 (-)-oxodicyclopentadiene 的前体，具有极佳的光学和化学收率。

  DOI：

  10.1039/a702910a
• 作为产物：
  描述：

  2,5-二氢-2,5-二甲氧基-2-甲基呋喃 在 硫酸 作用下， 生成 (1R,2S,3R,4S)-3-Acetyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde
  参考文献：
  名称：

  闪蒸真空热取代取代的三环[5.2.1.0 2,6 ]癸烯的立体特异性全合成（±）戊霉素

  摘要：

  描述了从呋喃开始合成4-官能化的三环[5.2.1.0 2,6 ]癸烯。这些结构被证明是用于合成环戊烯类化合物如戊霉素和类似物的合适的前体。

  DOI：

  10.1016/0040-4039(82)80158-5

文献信息

• First Exclusive Regioselective Fragmentation of Primary Ozonides Controlled by Remote Carbonyl Groups and a New Method for Determining the Regiochemistry of Carbonyl Oxide Formation
  作者：Hsien-Jen Wu、Chu-Chung Lin

  DOI：10.1021/jo952284p

  日期：1996.1.1

  The first exclusive regioselective fragmentation of primary ozonides controlled by remote carbonyl groups on ozonolysis of norbornene derivatives and reaction of final ozonides with triethylamine as a new probe for determining the regiochemistry of carbonyl oxide formation from primary ozonide fragmentation are reported. Ozonolysis of the endo adducts 3a-d and the deuterated compounds 8a and 8b in

  据报道，在降冰片烯衍生物的臭氧分解中，由远端羰基控制的伯氮氧化物的第一个排他性区域选择性断裂是最终的臭氧化物，以及最终的臭氧化物与三乙胺的反应，作为确定伯臭氧化物断裂形成羰基氧化物的区域化学的新探针。内加合物3a-d和氘代化合物8a和8b在CDCl（3）中于-78摄氏度进行臭氧分解，分别得到最终的臭氧化物4a-d，9a和9b作为唯一产物（> 95％）。没有获得可检测量的异构的最终臭氧化物5、10、11和12。提出了一种机制来解释初级臭氧化物的排他性区域选择性断裂。3a-d，8a的臭氧分解 在-78℃下在CH（2）Cl（2）中添加8b和8b，然后分别用三乙胺处理，分别以85-90％的收率得到凸四氧杂环己烷笼化合物16a-d，19a和19b。没有获得可检测量的其他区域异构体17a-d，20a和20b。在-78℃下于CH（2）Cl（2）中对3a-d，8a和8b进行臭氧分解，然后用二甲基硫醚还原，
• Synthesis of Diacetal Trioxa-cage Compounds via Reaction of Bicyclo[2.2.1]heptenes and Bicyclo[2.2.2]octenes with Dimethyldioxirane
  作者：Hui-Chang Lin、Hsien-Jen Wu

  DOI：10.1016/s0040-4020(99)00997-7

  日期：2000.1

  A new entry for the synthesis of diacetal trioxa-cage compounds via oxirane-induced sequential cyclization reaction of 2,3-bis-endo-diacylbicyclo[2.2.1]-5-heptenes and 2,3-bis-endo-diacylbicyclo[2.2.2]-5-octenes is reported. In the case of bicyclo[2.2.2]octenes, sequential cyclization reaction induced by iodine as electrophile failed. We have also demonstrated that dimethyldioxirane can selectively

  通过环氧乙烷诱导的2,3-双-内-二酰基双环[2.2.1] -5-庚烯和2,3-双-内-二酰基双环[2.2 ]的环氧乙烷顺序环化反应合成二缩醛三氧杂笼化合物的新方法.2] -5-辛烯的报道。在双环[2.2.2]辛烯的情况下，碘作为亲电试剂引起的顺序环化反应失败。我们还证明了二甲基二环氧乙烷可以选择性地氧化半缩醛以产生具有完整仲羟基的内酯。
• Lipase–triethylamine-mediated dynamic transesterification of a tricyclic acyloin having a latent meso-structure: a new route to optically pure oxodicyclopentadiene
  作者：Takahiko Taniguchi、Kunio Ogasawara

  DOI：10.1039/a702910a

  日期：——

  The racemic tricyclic acyloin (±)-endo-3-hydroxytricyclo[4.2.1.0 2,5 ]non-7-en -4-one has been dynamically resolved via the transient formation of the meso-enediol isomer under lipase–triethylamine-mediated kinetic transesterification conditions to give the single chiral acetate (-)-endo-3-acetoxytricyclo[4.2.1.0 2,5 ]non-7-en- 4-one, serving as a precursor of (-)-oxodicyclopentadiene, in excellent optical and chemical yields.

  在脂肪酶三乙胺介导的动力学酯交换反应条件下，通过瞬时形成中烯二醇异构体，动态解析了外消旋三环丙烯(±)-内向-3-羟基三环[4.2.1.0 2,5 ]壬-7-烯-4-酮，得到了单一手性乙酸酯(-)-内向-3-乙酰氧基三环[4.2.1.0 2,5 ]非-7-烯-4-酮，作为 (-)-oxodicyclopentadiene 的前体，具有极佳的光学和化学收率。
• Synthesis of 3,11-Dioxatetracyclo[6.3.0.0^2,6.0^5,9]undecanes and 3,5,7-Trioxapentacyclo[7.2.1.0^2,8.0^4,11.0^6,10]dodecane
  作者：Hui-Chang Lin、Chung-Yi Wu、Hsien-Jen Wu

  DOI：10.1002/jccs.199700094

  日期：1997.12

  AbstractThe synthesis of 3,11‐dioxatetracyclo[6.3.0.02,6.05,9]undecanes has been accomplished from furans in a short sequence by iodine‐induced cyclization reaction. The application of iodine‐induced cyclization reaction for the synthesis of 3,5,7‐trioxapentacyclo[7.2.1.02,8.04,11.06,10]dodecane itself was also demonstrated.
• Synthesis of New Type Diacetal Trioxa-Cage Compounds via an Intramolecular Nucleophilic Addition of the Hydroxy Group to the Carbonyl Oxide Group
  作者：Hsien-Jen Wu、Ching-Shiun Chao、Chu-Chung Lin

  DOI：10.1021/jo980632s

  日期：1998.10.1

  The synthesis of diacetal trioxa-cage compounds with a new type of skeleton is reported. Ozonolysis of the diols 2a-f, 21, 24, and 33 in CH2Cl2 at -78 degrees C followed by reduction with Me2S gave the diacetal trioxa-cages 3a-f, 22, 25, and 34 in 70-80% yields, respectively. A mechanism via an intramolecular nucleophilic addition of the hydroxy group of the diols to the carbonyl oxide group is proposed for the formation of the diacetal trioxa-cages. The effect of the number of carbon atoms at the bridge of the diols on the formation of the diacetal trioxa-cage skeleton was examined. Ozonolysis of the diols 13 and 15 under the same reaction conditions gave compounds 16 and 18, respectively. No detectable amount of the trioxa-cages 17 and 19 was obtained. For the synthesis of the diacetal trioxa-cages 28a-c and 31, which possess an alkene bond intact, ozonolysis of the diols 27a-c and 30 was performed by controlling the amount of ozone.