(3S,4R)-3-methyl-4-(3-oxobutyl)cyclopentan-1-one | 89822-14-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R)-3-methyl-4-(3-oxobutyl)cyclopentan-1-one
• CAS: 89822-14-0
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: PLFPEYANYWRYLU-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-methyl-4-(3-oxobutyl)cyclopentan-1-one 在 palladium on activated charcoal potassium hydrogensulfate 、 氢气 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.0h， 生成 (3S,3aS,6S,6aS)-3,6-Dimethyl-hexahydro-pentalen-1-one
  参考文献：
  名称：

  The Potential of Semiochemicals for Control ofPhorodon humuli(Homoptera: Aphididae)

  摘要：

  Field experiments employing yellow water-traps with vials releasing methyl salicylate, butyl isothiocyanate, 4-pentenyl isothiocyanate and diethyltoluamide were conducted during the spring migration of Phorodon humuli (Schrank), with the aim of identifying substances which might be used in the field to deter landing on hop plants. Methyl salicylate and the two isothiocyanates reduced trap catches of P. humuli. During the spring of 1994 a slow-release formulation of methyl salicylate and a beta-acid-rich hop resin sprayed on to hop plants did not reduce aphid infestations significantly. In autumn cis,cis-nepetalactol the main component of P. humuli's sex pheromone, prepared by various synthetic routes, increased trap catches of males and gynoparae equally. Catches of males in pheromone traps situated in a hop garden decreased with increasing trap height. Catches of males in traps charged with increasing doses of the cis,cis-nepetalactol peaked at 1 mg and then plateaued, whereas catches of gynoparae peaked similarly at 1 mg and then decreased. The effects of kairomones from an extract of the primary host, sex pheromone and a visual cue from yellow compared with clear water-traps were additive. The prospects for developing a semiochemicals-based control strategy against P. humuli, using some or all of the above elements, are discussed.

  DOI：

  10.1002/(sici)1096-9063(199612)48:4<293::aid-ps479>3.0.co;2-5
• 作为产物：
  描述：

  (3R,4S)-3-(3-Hydroxy-butyl)-4-methyl-cyclopentanone 生成 (3S,4R)-3-methyl-4-(3-oxobutyl)cyclopentan-1-one
  参考文献：
  名称：

  A novel synthesis of cis-3,4-disubstituted cyclopentanones

  摘要：

  DOI：

  10.1016/s0040-4039(01)80074-5

文献信息

• Asymmetric cyclization reactions. Cyclization of substituted 4-pentenals into cyclopentanone derivatives by rhodium(I) with chiral ligands
  作者：Yukari Taura、Masakazu Tanaka、Xiao-Ming Wu、Kazuhisa Funakoshi、Kiyoshi Sakai

  DOI：10.1016/s0040-4020(01)80954-6

  日期：1991.1

  Asymmetric cyclization of substituted 4-pentenals (Ia,b,c; IIa,b,c,d) by Rh(I) with chiral ligands was tested, and substrate (IId) with a bulkier substituent at C4 underwent more stereoselective cyclization by Rh(I)-((+)-DIPMC) to yield substituted cyclepentanone (IIID). The Rh(I) with (+)-DIPMC was found to proceed in a different manner from the Wilkinson-catalyzed cyclization.

  测试了Rh（I）与手性配体对取代的4-戊烯（Ia，b，c; IIa，b，c，d）的不对称环化作用，并在C 4处具有更大取代基的底物（IId）通过Rh（I）-（（+）-DIPMC）生成取代的环戊酮（IIID）。发现具有（+）-DIPMC的Rh（I）以不同于威尔金森催化的环化的方式进行。
• Highly enantioselective cyclization using cationic Rh(I) with chiral ligand
  作者：Xiao-Ming Wu、Kazuhisa Funakoshi、Kiyoshi Sakai

  DOI：10.1016/s0040-4039(00)60966-8

  日期：1992.10

  (>99% de) of 3R (or S) 3,4-disubstituted 4-pentenals into the corresponding 3,4-cis(or trans)-disubstituted cyclopentanone and highly enantioselective cyclization (>99% ee) of 4-substituted 4-pentenals into 3-substituted cyclopentanone were achieved by using cationic Rh+(BINAP)ClO4−.

  3R（或S）3,4-二取代的4-戊烯的非对映选择性环化（> 99％de）转化为相应的3,4-顺（或反式）-二取代的环戊酮和4的高度对映选择性环化（> 99％ee） -取代的4-戊烯醛为3-取代环戊酮通过使用阳离子铑达到+（BINAP）CLO 4 - 。
• An insight into the novel ring transformation reactions using ethylene glycol/BF3
  作者：Takayoshi Yamamoto、Hiroshi Suemune、Kiyoshi Sakai

  DOI：10.1016/s0040-4020(01)82395-4

  日期：1991.9

  The ring transformation of cyclic ketones with a carbonyl function at the side chain under acetalization conditions (BF3/ethylene glycol) was studied. The results suggested that this reaction proceeds via acetal pathway as a cis-Cyclohexane-1,2-diol was found to be more effective than cis-Cyclohexane-1,2-diol was found to be more effective than ethylene glycol for this ring transformation.
• SAKAI, K.;ISHIGURO, Y.;FUNAKOSHI, K.;UENO, K.;SUEMUNE, H., TETRAHEDRON LETT., 1984, 25, N 9, 961-964
  作者：SAKAI, K.、ISHIGURO, Y.、FUNAKOSHI, K.、UENO, K.、SUEMUNE, H.

  DOI：——

  日期：——