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3-cyanopropylcyclopentanone | 128893-49-2

中文名称
——
中文别名
——
英文名称
3-cyanopropylcyclopentanone
英文别名
4-(2-Oxocyclopentyl)butanenitrile
3-cyanopropylcyclopentanone化学式
CAS
128893-49-2
化学式
C9H13NO
mdl
——
分子量
151.208
InChiKey
CPQVALOVUFCZAE-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    297.8±13.0 °C(Predicted)
  • 密度:
    1.013±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    0.8
  • 重原子数:
    11
  • 可旋转键数:
    3
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.78
  • 拓扑面积:
    40.9
  • 氢给体数:
    0
  • 氢受体数:
    2

反应信息

  • 作为反应物:
    描述:
    3-cyanopropylcyclopentanone 在 lithium aluminium tetrahydride 、 四乙基对甲苯磺酸铵甲基磺酰氯三乙胺 作用下, 以 四氢呋喃异丙醇 为溶剂, 反应 9.0h, 生成 (1α,6α)-Bicyclo<4.3.0>nonan-1-ol
    参考文献:
    名称:
    Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.
    摘要:
    Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.
    DOI:
    10.1021/jo00052a036
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文献信息

  • Electroreductive intramolecular coupling of γ- and δ-cyanoketones
    作者:Tatsuya Shono、Naoki Kise
    DOI:10.1016/s0040-4039(00)88791-2
    日期:1990.1
    Electroreduction of γ- and δ-cyanoketones in i-PrOH gave cyclized products α-hydroxyketones and their dehydroxylated ketones, and this reaction was applied to the synthesis of dihydrojasmone, methyl dihydrojasmonate, and Rosaprostol.
    在i-PrOH中电还原γ-和δ-氰基酮,生成环化产物α-羟基酮及其脱羟基酮,并将该反应用于二氢茉莉酮,二氢茉莉酮酸甲酯和Rosaprostol的合成。
  • Cp2TiPh-coordinated cyano and ester groups as efficient ketyl radical acceptors in the reductive radical cyclization of γ- and δ-cyano ketones and δ-keto esters
    作者:Yoshihiko Yamamoto、Daisuke Matsumi
    DOI:10.1039/a800661j
    日期:——
    Cp2TiPh promotes the reductive radical cyclization of γ- and δ-cyano ketones and δ-keto esters to give α-hydroxycycloalkanones in moderate to good yields; the titanium reagent coordinates to both the ketone and the cyano or ester terminus, the LUMO of the cyano or ester group is thus lowered, and cyclization proceeds irreversibly without formation of the unstable iminyl or alkoxy radical intermediates.
    Cp2TiPh促进了γ-和δ-氰基酮及δ-酮酯的还原自由基环化,得到α-羟基环状酮,产率适中到良好;钛试剂与酮和氰基或酯末端均形成配位,氰基或酯基团的LUMO因此降低,环化过程不可逆进行,不会形成不稳定的亚胺或烷氧自由基中间体。
  • The Cp<sub>2</sub>TiPh-Mediated Reductive Radical Cyclization of Cyanoketones and Related Reactions. Efficient Trapping of Ketyl Radicals by Cp<sub>2</sub>TiPh-Coordinated Polar Multiple Bonds
    作者:Yoshihiko Yamamoto、Daisuke Matsumi、Reiko Hattori、Kenji Itoh
    DOI:10.1021/jo982492s
    日期:1999.4.1
    The reductive radical cyclization of cyanoketones was achieved using Cp2TiPh. The Ti(III) reagent was prepared by the sequential addition of i-PrMgCl and PhMgBr to commercial Cp2TiCl2 in this order and used effectively without isolation. The cyclization of the gamma- and delta-cyanoketones was performed in toluene at ambient temperature for several hours to give alpha-hydroxycyclopentanones and hexanones in moderate to good yields, respectively. The titanium reagent independently coordinates to both the carbonyl and cyano termini. As a result of lowering the LUMO of the cyano group upon coordination of the Ti(III) species, the irreversible cyclization successfully proceeds without formation of the unstable iminyl radical intermediate. The ester group can also be activated by the coordination of Cp2TiPh, and aromatic ketones with an ester group at the gamma position are cyclized to give the corresponding alpha-hydroxyketones.
  • Intramolecular Ketone−Nitrile Reductive Coupling Reactions Promoted by Samarium(II) Iodide
    作者:Gary A. Molander、Chad N. Wolfe
    DOI:10.1021/jo981537m
    日期:1998.11.1
    Samarium(II) iodide (SmI2) has been successfully utilized as a reducing agent for the intramolecular coupling of ketones with nitriles. The use of visible light to promote the reductive coupling represents an improvement over previously reported protocols. The procedure also avoids overreduction of the resulting alpha-hydroxy ketones. Monocyclic, fused bicyclic, and bridged bicyclic alpha-hydroxy ketones composed of a number of substitution patterns have been synthesized in moderate to excellent yield via this method. A sequential reaction consisting of a nucleophilic acyl substitution followed by a ketyl-nitrile coupling has also been accomplished.
  • SHONO, TATSUYA;KISE, NAOKI, TETRAHEDRON LETT., 31,(1990) N, C. 1303-1306
    作者:SHONO, TATSUYA、KISE, NAOKI
    DOI:——
    日期:——
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