3-(4-oxopentyl)cyclohexanone | 133549-40-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-oxopentyl)cyclohexanone
• 英文别名: 3-(4-Oxopentyl)cyclohexan-1-one
• CAS: 133549-40-3
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: GWIYYOXKFGCJDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯-2-戊酮 在 盐酸 、 naphthalen-1-yl-lithium 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 3-(4-oxopentyl)cyclohexanone
  参考文献：
  名称：

  2-（3-Lithiopropyl）-和2-（3-lithiopropyl）-2-methyl-1,3-dioxolane：合成双官能化化合物中的新蒙版双烯酸锂

  摘要：

  通过在-78℃下用萘二甲酸锂对相应的氯化前体进行锂化来预沉积2-（3-Lithiopropyl）-和2-（3-lithiopropyl）-2-甲基-1,3-二氧戊环（2）。这些被掩盖的双歧烯酸酯与不同的亲电试剂的反应产生了预期的单保护的羰基官能化合物（3-12），在酸性条件下可以很容易地对其进行脱保护。

  DOI：

  10.1016/s0040-4039(00)97465-3

文献信息

• Tandem Conjugate Reduction−Aldol Cyclization Using Stryker's Reagent
  作者：Pauline Chiu、Chun-Pong Szeto、Zhe Geng、Kin-Fai Cheng

  DOI：10.1021/ol015944n

  日期：2001.6.1

  [see reaction]. Conjugate reduction by Stryker's reagent to form copper enolates, followed by intramolecular aldol cyclization, successfully generated five- and six-membered carbocycles in one pot efficiently. This tandem reaction is generally diastereoselective and provides good yields of the beta-hydroxyketones without any dehydration at low temperatures.

  [请参阅反应]。用Stryker试剂还原还原形成烯醇铜，然后分子内羟醛环化，可在一个锅中有效地成功生成五元和六元碳环。该串联反应通常是非对映选择性的，并提供良好的β-羟基酮收率，且在低温下不发生任何脱水。
• Masked lithium bishomoenolates: useful intermediates in organic synthesis
  作者：Diego J. Ramon、Miguel Yus

  DOI：10.1021/jo00012a012

  日期：1991.6

  The lithiation of the chloro ketals 9 with lithium naphthalenide at -78-degrees-C led to the corresponding masked lithium bishomoenolates 4, which are stable species under these conditions and react with different electrophilic reagents (H2O, D2O, i-PrCHO, PhCHO, MeCOEt, (activated CH2)4CO, (activated CH2)5CO, (activated CH2)7CO, PhCOMe, c-C3H5COPh, PhCN, HCONMe2, PrCO activated N(CH2)4, PhCO activated N(CH2)4, PhCOCl, EtOCOCl, PhCHNPh, and (PhCH2S)2) to give, after hydrolysis with water, the corresponding bifunctionalized compounds 10a-22a, 10b-22b, and 10c-15c. When alkyl halides were used as electrophiles the reaction failed. In the presence of a catalytic amount of the complex CuBr.Me2S, the same reaction with alpha,beta-unsaturated ketones (methyl vinyl ketone or 2-cyclohexanone) yielded the expected products of a 1,4-addition 25a-c and 26b. The deprotection of the masked carbonyl group was easily done by treatment with 2 N hydrochloric acid in THF, so as examples, compounds 27a-29a, 30b, 31b, 32c, and 33c were isolated. The transformation of hemiacetals of the type 27a into substituted tetrahydropyrans was carried out by means of compounds of the type R3SiNu (Nu = H, allyl, CN) in the presence of BF3, so products 34a-41a, 42b, and 43b were prepared. Finally, the in situ oxidation of the deprotected products of the type 27a-arising from the reaction of bishomoenolate 4a with carbonyl compounds-with Jones reagent (for ketones derivatives) or PCC (for aldehydes derivatives) led to the corresponding delta-lactones 44-57.
• RAMON, DIEGO J.;YUS, MIGUEL, J. ORG. CHEM., 56,(1991) N2, C. 3825-3831
  作者：RAMON, DIEGO J.、YUS, MIGUEL

  DOI：——

  日期：——
• 2-(3-Lithiopropyl)- and 2-(3-lithiopropyl)-2-methyl-1,3-dioxolane: New masked lithium bishomoenolates in the synthesis of bifunctionalized compounds
  作者：Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4039(00)97465-3

  日期：——

  2-(3-Lithiopropyl)- and 2-(3-lithiopropyl)-2-methyl-1,3-dioxolane (2) are prepaned by lithiation of the corresponding chlorinated precursors with lithium naphthalenide at −78°C. The reaction of these masked bishomoenolates with different electrophiles yields the expected monoprotected functional carbonyl compounds (3–12), which can be easily deprotected under acid conditions.

  通过在-78℃下用萘二甲酸锂对相应的氯化前体进行锂化来预沉积2-（3-Lithiopropyl）-和2-（3-lithiopropyl）-2-甲基-1,3-二氧戊环（2）。这些被掩盖的双歧烯酸酯与不同的亲电试剂的反应产生了预期的单保护的羰基官能化合物（3-12），在酸性条件下可以很容易地对其进行脱保护。