3-formylmethylcyclopentan-1-one | 66972-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-formylmethylcyclopentan-1-one
• 英文别名: 3-(3-Ketocyclopentyl)-propan-1-al；(3-Oxo-cyclopentyl)-acetaldehyd；2-(3-Oxocyclopentyl)acetaldehyde
• CAS: 66972-67-6
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: YDCUQMSVRRIWKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (2R,3R)-(-)-2,3-丁二醇 、 3-formylmethylcyclopentan-1-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 (2R,3R)-7-((4R,5R)-4,5-Dimethyl-[1,3]dioxolan-2-ylmethyl)-2,3-dimethyl-1,4-dioxa-spiro[4.4]nonane
  参考文献：
  名称：

  Remarkable enantioselective 1,4-addition reactions of chiral allylphosphonyl anions (ambident nucleophiles) with cyclic enones (ambident electrophiles)

  摘要：

  DOI：

  10.1021/ja00250a047
• 作为产物：
  描述：

  3-氧代-环戊烷乙酸 在 palladium on barium sulfate 草酰氯 、 氢气 作用下， 生成 3-formylmethylcyclopentan-1-one
  参考文献：
  名称：

  Kozlowska,M.; Sobotka,W., Polish Journal of Chemistry, 1978, vol. 52, p. 347 - 352

  摘要：

  DOI：

文献信息

• Anodic oxidations of electron-rich olefins: radical cation based approaches to the synthesis of bridged bicyclic ring skeletons
  作者：S.Hari Krishna Reddy、Kazuhiro Chiba、Yongmao Sun、Kevin D Moeller

  DOI：10.1016/s0040-4020(01)00358-1

  日期：2001.6

  intramolecular anodic olefin coupling reactions for building bicyclo[3.2.1]octane ring skeletons has been examined. While simple model systems using bis enol ether substrates readily led to the formation of bicyclic products, application of the reactions to total synthesis efforts were hindered by reactions forming dimethoxy acetal groups at both the terminating and initiating ends of the cyclization reactions

  已经研究了分子内阳极烯烃偶联反应在构建双环[3.2.1]辛烷环骨架中的应用。尽管使用双烯醇醚底物的简单模型系统容易导致双环产物的形成，但是由于在环化反应的末端和起始端均形成二甲氧基缩醛基团的反应阻碍了该反应在全合成工作中的应用。为了解决该问题，已经研究了基于乙烯酮缩醛的引发基团。烯酮二硫缩醛基的使用被证明对于该目的特别有用。
• Asymmetric Michael Addition Reactions of Chiral Prop-2-enyl- and But-2-enylphosphonate Anions with Cyclic Enones
  作者：Kiyoshi Tanaka、Yoshihisa Ohta、Kaoru Fuji

  DOI：10.1021/jo00129a051

  日期：1995.12

  Reactions of anions derived from chiral allyl- and crotylphosphonates with alpha,beta-unsaturated cyclic ketones took place at the gamma-position of the reagents and led to diastereomerically enriched products of conjugate addition, suggesting efficient enantiotopic face discrimination caused by remote asymmetric induction. Using mixtures of crotylphosphonates with different E/Z ratios, we found that the E/Z stereochemistry of the reagent was highly translated into the products. A tandem vicinal dialkylation based on Michael addition-enolate methylation was carried out to give the trans alpha,beta-dialkylated product with high selectivity. Oxidative cleavage of the Michael adducts resulted in the formation of the optically active delta-keto aldehyde corresponding to the formal conjugate addition of an acetaldehyde or a propionaldehyde anion equivalent to alpha,beta-unsaturated carbonyl compounds.
• Asymmetric Michael Addition Reaction of Phosphorus-Stabilized Allyl Anions with Cyclic Enones
  作者：Scott E. Denmark、Jung-Ho Kim

  DOI：10.1021/jo00128a028

  日期：1995.11

  The asymmetric Michael addition reaction of chirally modified P-allyl anions derived from enantiomerically enriched 2-allyl-1,3,2-oxazaphosphorinane 2-oxides has been investigated with cyclic enones. The racemic 1,3,2-oxazaphosphorinane 2-oxide 3 has been shown to be extremely diastereoselective in the Michael addition to 5-, 6-, and 7-ring enones. With the enantiomerically enriched 2-allyl-1,3,2-oxazaphosphorinane 2-oxides, high regio- and diastereoselectivities (88-90% diastereomeric excess) have been achieved in the Michael addition reaction of one of the diastereomers (cis series). The Michael reaction of the anions derived from the trans series were not diastereoselective (similar to 10% diastereomeric excess). The origin of the addition selectivity can be rationalized by (1) consideration of the structure and conformational preferences of the allyl anion (parallel conformation, s-trans, no lithium contact), (2) conformational analysis of the 1,3,2-oxazaphosphorinane 2-oxide ring (chair, equatorial allyl group) and (3) assumption of a 10-membered ring transition state structure with lithium coordination of the enone.
• Synthesis of homochiral 3-substituted cyclopentanones from 2-norbornanones
  作者：A. García Martínez、E. Teso Vilar、A. García Fraile、S. de la Moya Cerero、P. Martínez^Ruiz、L.R. Subramanian

  DOI：10.1016/0957-4166(96)00264-9

  日期：1996.8
• Kozlowska,M.; Sobotka,W., Polish Journal of Chemistry, 1978, vol. 52, p. 347 - 352
  作者：Kozlowska,M.、Sobotka,W.

  DOI：——

  日期：——