3-methyl-2-(2-methylethyl)-cyclopent-2-en-1-one | 50397-91-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-2-(2-methylethyl)-cyclopent-2-en-1-one
• 英文别名: 3-methyl-2-propyl-2-cyclopenten-1-one；3-methyl-2-propylcyclopent-2-en-1-one；2-propyl-3-methylcyclopent-2-enone；3-methyl-2-propyl-cyclopent-2-enone；3-Methyl-2-propyl-cyclopent-2-enon；2-n-propyl-3-methyl-2-cyclopentenone；2-Cyclopenten-1-one, 3-methyl-2-propyl-
• CAS: 50397-91-6
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: IAGSPEBQNJDWDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  94.5 °C(Press: 11.5 Torr)
• 密度：
  0.930±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  5-丁基-5-甲基四氢呋喃-2-酮 、 3-methyl-2-(2-methylethyl)-cyclopent-2-en-1-one 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  The Preparation of Cyclopentenones from Lactones

  摘要：

  DOI：

  10.1021/ja01184a026
• 作为产物：
  描述：

  乙酰丙酸乙酯 在 磷酸酐 、 磷酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 6.25h， 生成 3-methyl-2-(2-methylethyl)-cyclopent-2-en-1-one
  参考文献：
  名称：

  Unprecedented Rearrangement of a 4-Alkoxy-5-bromoalk-2-en-1-ol to a Cyclopentenone via an Iso-Nazarov Cyclization Process

  摘要：

  We report the structure determination of the product 9 of the rearrangement of the allylic alcohol 3 under very mild conditions, probably promoted by an acidic substance, and propose a reasonable mechanism for its formation.

  DOI：

  10.1021/jo071104w

文献信息

• Construction of polycyclic structures with vicinal all-carbon quaternary stereocenters <i>via</i> an enantioselective photoenolization/Diels–Alder reaction
  作者：Min Hou、Mengmeng Xu、Baochao Yang、Haibing He、Shuanhu Gao

  DOI：10.1039/d1sc00883h

  日期：——

  present in one molecule, they will dramatically increase its synthetic challenge. A chiral titanium promoted enantioselective photoenolization/Diels–Alder (PEDA) reaction allows largely stereohindered tetra-substituted dienophiles to interact with highly active photoenolized hydroxy-o-quinodimethanes, delivering fused or spiro polycyclic rings bearing vicinal all-carbon quaternary centers in excellent

  全碳四元立构中心在天然产物中普遍存在，并且在药物分子中具有重要意义。然而，由于化学环境拥挤，全碳立构中心的构建是一个具有挑战性的项目。而且，当一个分子中存在邻位全碳四元立构中心时，它们将极大地增加其合成挑战。手性钛促进的对映选择性光烯醇化/狄尔斯-阿尔德（PEDA）反应允许很大程度上立体受阻的四取代亲二烯体与高活性光烯醇化羟基-邻醌二甲烷相互作用，以优异的对映体过量提供带有邻位全碳四元中心的稠合或螺环多环通过一步操作。这种新开发的对映选择性 PEDA 反应将激发不对称激发态反应的其他进展，并可用于结构相关的复杂天然产物或药物分子的全合成，以进行药物发现。
• On the mechanism of the silicon-tethered reductive Pauson–Khand reaction
  作者：John F Reichwein、Scott T Iacono、Brian L Pagenkopf

  DOI：10.1016/s0040-4020(02)00337-x

  日期：2002.5

  The reductive Pauson–Khand reaction (PKR) of tethered vinyl silanes likely proceeds as usual to the bicyclopentenones 2, but rapid loss of the allylic silane initiates a fragmentation process culminating in propargylic carbon reduction. Damp nitrile solvents are crucial for efficient reaction, and under dry conditions additional products are obtained including dimerized cyclopentadienones and 5-(1-amino-alkylidine)

  系留的乙烯基硅烷的还原性Pauson-Khand反应（PKR）可能照常进行至双环戊烯酮2，但烯丙基硅烷的快速损失引发了一个裂解过程，最终导致了炔丙基碳的还原。潮湿的腈溶剂对于有效反应至关重要，在干燥条件下，还可以得到其他产物，包括二聚环戊二烯酮和5-（1-氨基-亚烷基吡啶）环戊烯。掺入溶剂的烯酮可能来自烯醇盐对钴配位腈的攻击。提出了统一的反应机理。还报道了具有烯丙氧基乙炔基硅烷的PKR的第一个实例。
• Process for preparing oxocyclopentene derivatives
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04970345A1

  公开（公告）日：1990-11-13

  A process for preparing oxocyclopentenes of the formula: ##STR1## wherein R.sup.1 is hydrogen, lower alkyl or lower alkenyl and R.sup.2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, substituted or unsubstituted aryl, ar(lower)alkyl, thienyl or cycloalkyl, which comprises subjecting a furan-carbinol of the formula: ##STR2## wherein R.sup.1 is as defined above and R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, substituted or unsubstituted aryl, ar(lower)alkyl, thienyl or cycloalkyl to rearrangement, subjecting the resultant hydroxycyclopentenone of the formula: ##STR3## wherein R.sup.1 and R.sup.3 are each as defined above to hydrogenation and subjecting the resulting hydroxycyclopentanone of the formula; ##STR4## wherein R.sup.1 and R.sup.2 are each as defined above to dehydration.

  制备氧代环戊烯的方法，其化学式为：其中R.sup.1为氢、低烷基或低烯基，R.sup.2为氢、低烷基、低烯基、低炔基、取代或未取代芳基、芳基(低)烷基、噻吩基或环烷基，包括将化学式为的呋喃-碳醇经过重排，得到化学式为的羟基环戊烯酮，然后将化学式为的羟基环戊烷酮进行氢化，最后将化学式为的羟基环戊酮进行脱水。
• Combination Therapy for the Treatment of Urinary Frequency, Urinary Urgency and Urinary Incontinence
  申请人：Gottesdiener Keith M.

  公开号：US20090270406A1

  公开（公告）日：2009-10-29

  This invention concerns compositions for the treatment of urinary frequency, urinary urgency and urinary incontinence comprising (R)-N-[4-[2-[[2-hydroxy-2-(pyridin-3-yl)ethyl]amino]ethyl]phenyl]-4-[4-(4-tri-fluoromethylphenyl)thiazol-2-yl]benzenesulfonamide and pharmaceutically acceptable salts thereof. In another aspect, this invention concerns combination therapy for urinary frequency, urinary urgency and urinary incontinence wherein one of the active agents is (R)-N-[4-[2-[[2-hydroxy-2-(pyridin-3-yl)ethyl]amino]ethyl]phenyl]-4-[4-(4-tri-fluoromethylphenyl)thiazol-2-yl]benzenesulfonamide and pharmaceutically acceptable salts thereof.

  这项发明涉及用于治疗尿频、尿急和尿失禁的组合物，包括(R)-N-[4-[2-[[2-羟基-2-(吡啶-3-基)乙基]氨基]乙基]苯基]-4-[4-(4-三氟甲基苯基)噻唑-2-基]苯磺酰胺及其药学上可接受的盐。另一方面，这项发明涉及用于尿频、尿急和尿失禁的联合疗法，其中一种活性药物是(R)-N-[4-[2-[[2-羟基-2-(吡啶-3-基)乙基]氨基]乙基]苯基]-4-[4-(4-三氟甲基苯基)噻唑-2-基]苯磺酰胺及其药学上可接受的盐。
• Cyclocarbonylation of silicon tethered enynes derived from propargylic alcohols and vinylsilanes: a new reductive Pauson–Khand reaction with a traceless tether
  作者：John F. Reichwein、Scott T. Iacono、Mittun C. Patel、Brian L. Pagenkopf

  DOI：10.1016/s0040-4039(02)00634-2

  日期：2002.5

  In nitrile solvents vinylsilyl ethers of propargylic alcohols undergo Pauson–Khand reaction with polysiloxane extrusion and concomitant reduction of the propargylic CO bond. The product enones are formally the result of an intermolecular PKR reaction with ethylene.

  在腈溶剂中，炔丙醇的乙烯基甲硅烷基醚会发生Pauson-Khand反应，并伴随聚硅氧烷的挤出并伴随着丙炔基的C bondO键的还原。产物烯酮形式上是与乙烯的分子间PKR反应的结果。