2-(3'-bromopropyl)cyclopentanone | 10468-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3'-bromopropyl)cyclopentanone
• 英文别名: 2-(3-Bromopropyl)cyclopentan-1-one
• CAS: 10468-38-9
• 化学式: C₈H₁₃BrO
• 分子量: 205.095
• InChiKey: YXQTWFZXGVXHJR-UHFFFAOYSA-N

物化性质

• 沸点：
  100 °C(Press: 2 Torr)
• 密度：
  1.3370 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3'-bromopropyl)cyclopentanone 在 乙醚 、 magnesium 作用下， 生成 2,3,4,5,6,6a-hexahydro-1H-pentalen-3a-ol
  参考文献：
  名称：

  Selinskii; Elagina, Doklady Akademii Nauk SSSR, 1952, vol. 86, p. 1117

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲氧羰基环戊酮 在 potassium tert-butylate 、 氢溴酸 作用下， 反应 51.0h， 生成 2-(3'-bromopropyl)cyclopentanone
  参考文献：
  名称：

  叠氮化物与碳正离子的分子内施密特反应：桥联双环和稠合双环叔胺的合成

  摘要：

  脂肪族叠氮化物被碳正离子分子内捕获，产生氨基重氮离子中间体。然后发生碳氮重排，产生桥连或稠合双环 a-氨基碳正离子或亚胺离子，具体取决于 C(+)-N 键的几何形状。在桥接系统中，α-氨基碳阳离子的快速消除产生具有 1-氮杂双环 [3.2.2] 壬烯、1-氮杂双环 [2.2.2] 辛烯和 1-氮杂双环 [3.2.1] 辛烯骨架的扭曲烯胺。在稠合系统中，亚胺离子被硼氢化钠还原为 1-氮杂双环 [n.3.0] 烷烃，其中 n=4 或 5。这些分子内施密特反应的碳正离子是通过用三氟甲磺酸处理烯烃或醇而产生的

  DOI：

  10.1021/ja00075a038

文献信息

• The Synthesis of Cycloalkenes by the IntramolecularWittig Reaction
  作者：Konrad B. Becker

  DOI：10.1002/hlca.19770600110

  日期：1977.1.26

  A simple synthesis of a series of bicyclo[m.n.0]-1-alkenes (m, n = 3,4,5) from 2-oxocycloalkanecarboxylates by the intramolecular Wittig reaction is reported (see p. 70–72). The spectral properties (IR., 1H-NMR. and 13C-NMR.) of these annulated trisubstituted olefins are discussed.

  据报道，通过分子内的Wittig反应由2-氧代环烷羧酸酯简单地合成了一系列双环[mn0] -1-烯烃（m，n = 3,4,5）（参见第70-72页）。讨论了这些环状三取代烯烃的光谱性质（IR，1 H-NMR和13 C-NMR）。
• A concise synthetic pathway towards 5-substituted indolizidines
  作者：Tamás R. Varga、Péter Nemes、Zoltán Mucsi、Pál Scheiber

  DOI：10.1016/j.tetlet.2006.12.074

  日期：2007.2

  The total synthesis of 5-(2′-hydroxyethyl)indolizidine via 5-thioindolizidinone is described. The key step is the transformation of 5-thioindolizidinone via Eschenmoser’s sulfide contraction. The racemic mixture of 5R,9R- and 5S,9S-5-(2′-hydroxyethyl)indolizidine was obtained in seven steps in 17% overall yield from 2-allyl cyclopentanone.

  描述了通过5-硫代吲哚并咪唑酮的5-（2'-羟乙基）吲哚唑烷的全合成。关键步骤是通过Eschenmoser的硫化物收缩转化5-thioindolizidinone。从2-烯丙基环戊酮以七个步骤以总收率的17％获得了5 R，9 R-和5 S，9 S -5-（2'-羟乙基）吲哚并咪唑的外消旋混合物。
• Intramolecular Schmidt reactions of azides with carbocations: synthesis of bridged-bicyclic and fused-bicyclic tertiary amines
  作者：William H. Pearson、Rajesh Walavalkar、Jeffrey M. Schkeryantz、Wen Kui Fang、James D. Blickensdorf

  DOI：10.1021/ja00075a038

  日期：1993.11

  Aliphatic azides were captured intramolecularlyby carbocations, producing aminodiazonium ion intermediates. Carbon-to-nitrogen rearrangement then occurred, generating bridged- or fused-bicyclic a-amino carbocations or iminium ions, depending on the geometry about the C(+)-N bond. In the bridged systems, rapid elimination of the α-amino carbocations produced twisted enamines with 1-azabicyclo[3.2.2]nonene

  脂肪族叠氮化物被碳正离子分子内捕获，产生氨基重氮离子中间体。然后发生碳氮重排，产生桥连或稠合双环 a-氨基碳正离子或亚胺离子，具体取决于 C(+)-N 键的几何形状。在桥接系统中，α-氨基碳阳离子的快速消除产生具有 1-氮杂双环 [3.2.2] 壬烯、1-氮杂双环 [2.2.2] 辛烯和 1-氮杂双环 [3.2.1] 辛烯骨架的扭曲烯胺。在稠合系统中，亚胺离子被硼氢化钠还原为 1-氮杂双环 [n.3.0] 烷烃，其中 n=4 或 5。这些分子内施密特反应的碳正离子是通过用三氟甲磺酸处理烯烃或醇而产生的
• Stereoisomers of cyclopentano-tetrahydropyran
  作者：M. Procházka、J.V. Černý

  DOI：10.1016/0040-4020(61)80051-3

  日期：1961.1

  Cis- and trans-cyclopentano(b)tetrahydropyrans were prepared and the validity of Auwers-Skita's rule confirmed. The relatively low differences of the constants of the substances prepared were explained, with regard to the analogous hydrindans, by a more planar arrangement of the rings. During the cyclization reaction, which was carried out by means of chromatography on aluminium oxide, a significant

  制备了顺式和反式-环戊烷（b）四氢吡喃，并证实了Auwers-Skita法则的有效性。通过类似的环，通过环的更平坦的布置，解释了所制备的物质的常数的相对较低的差异。在通过色谱法在氧化铝上进行的环化反应期间，注意到吸收剂的显着的空间传导影响。
• Intramolecular nucleophilic acyl substitution reactions of halo-substituted esters and lactones. New applications of organosamarium reagents
  作者：Gary A. Molander、Jeffrey A. McKie

  DOI：10.1021/jo00077a053

  日期：1993.12

  Intramolecular nucleophilic acyl substitution reactions involving a broad range of halo substituted carboxylic acid derivatives have been accomplished in excellent yield employing samarium(II) iodide as the reductive coupling agent. Although particular substrates cyclized most effectively in THF in the presence of tripiperidinophosphine oxide, carboxylic acid esters, the focus of this report, cyclize equally well without such an additive in the presence of a catalytic quantity of iron(III) complexes. Thus a comprehensive series of halo substituted esters were cyclized in excellent yield to the corresponding 4-, 5-, and 6-membered carbocycles. The reaction is extremely mild and selective as demonstrated by experiments wherein alkyl chlorides, acetals, and olefins remain completely intact under the reaction conditions. In addition to introducing a convenient procedure for preparing stereodefined spirocyclic systems, a new ring expansion sequence has been developed that appears extremely general for the preparation of various ring systems.