(±)-methyl 2-methyl-5-oxocyclopentanecarboxylate | 18067-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (±)-methyl 2-methyl-5-oxocyclopentanecarboxylate
• 英文别名: 3-methyl-cyclopentanon-2-carbonsaeuremethylester；methyl 5-methyl-2-oxocyclopentane-1-carboxylate；methyl 2-methyl-5-oxocyclopentane carboxylate；2-carbomethoxy-3-methylcyclopentanone；2-Methoxycarbonyl-3-methyl-cyclopentanon；2-Carbomethoxy-3-methylcyclopentanon；Methyl 2-methyl-5-oxocyclopentane-1-carboxylate
• CAS: 18067-33-9
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: SVYJAKSNXZQAQI-UHFFFAOYSA-N

物化性质

• 沸点：
  90-92 °C(Press: 12 Torr)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-methyl 2-methyl-5-oxocyclopentanecarboxylate 在 六甲基磷酰三胺 、 偶氮二异丁腈 、 氢溴酸 、 三正丁基氢锡 、 sodium hydride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 33.0h， 生成 methyl 2-methyl-5-oxocyclooctane carboxylate
  参考文献：
  名称：

  通过串联自由基环扩展/环化合成稠合双环：评估竞争性分子内反应。

  摘要：

  环戊酮和环己酮的一碳和三碳“ Dowd-Beckwith”环扩容通常是成功的，但是竞争性工艺可能会损害串联扩容/环化反应。对环膨胀，1,5-氢转移和6- exo环化之间竞争的评估提供了有关如何设计成功的串联膨胀环化序列的信息。

  DOI：

  10.1016/s0040-4020(98)00467-0
• 作为产物：
  描述：

  5-甲基-2-(1-甲基亚乙基)环己酮 在 臭氧 作用下， 以 四氯化碳 、 乙醚 为溶剂， 生成 (±)-methyl 2-methyl-5-oxocyclopentanecarboxylate
  参考文献：
  名称：

  Photodimeric cage compounds. IV. Transformations of the cyclobutenes formed on degradation of the photodimers of 2,6-dimethyl-and 2,6-diethyl-4-pyrone

  摘要：

  DOI：

  10.1021/ja01045a028

文献信息

• Ring opening of cyclopropylketones induced by photochemical electron transfer
  作者：Janine Cossy、Nathalie Furet、Samir BouzBouz

  DOI：10.1016/0040-4020(95)00727-p

  日期：1995.10

  Depending on the substitution pattern of cyclopropylketones, the photochemically induced electron transfer of tertiary amines to cyclopropylketones leads either to the formation of 3-substituted cycloalkanones or to ring expanded products.

  根据环丙基酮的取代方式，光化学诱导的叔胺电子转移至环丙基酮会导致3-取代的环烷酮的形成或环扩产物。
• Photochemical ring opening of cyclopropyl ketones induced by electron transfer
  作者：Janine Cossy、Nathalie Furet

  DOI：10.1016/s0040-4039(00)61464-8

  日期：1993.12

  Irradiation of substituted bicyclo[n.1.0]alkan-2-ones at 254 nm in the presence of triethylamine and lithium perchlorate (LiClO4) can lead to cyclopropane ring opening with cleavage of the C(1)-C(n+2) (ring enlargement) or C(1)-C(n+3) bonds.

  在存在三乙胺和高氯酸锂（LiClO 4）的情况下，在254 nm处辐照取代的双环[n.1.0]烷-2-酮可导致环丙烷开环，并裂解C（1）-C（n + 2） （环扩大）或C（1）-C（n + 3）键。
• [EN] CYCLOHEXEN-1-YL-PYRIDIN-2-YL-1H-PYRAZOLE-4-CARBOXYLIC ACID DERIVATIVES AND THE USE THEREOF AS SOLUBLE GUANYLATE CYCLASE ACTIVATORS<br/>[FR] DÉRIVÉS DE L'ACIDE CYCLOHEXÉN-1-YL-PYRIDIN-2-YL-1H-PYRAZOLE-4-CARBOXYLIQUE ET UTILISATION DE CEUX-CI EN TANT QU'ACTIVATEURS DE LA GUANYLATE CYCLASE SOLUBLE
  申请人：NOVARTIS AG

  公开号：WO2016001878A1

  公开（公告）日：2016-01-07

  The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了化合物的公式（I）或其药学上可接受的盐；本发明的化合物的制备方法及其治疗用途。本发明还提供了药理活性剂的组合和药物组合物。
• Alkylation of carbonyl compounds with ω-iodo-2-trimethylstannylalk-1-enes. Novel annulation sequences leading to diene systems
  作者：Edward Piers、Richard W. Friesen、Brian A. Keay

  DOI：10.1039/c39850000809

  日期：——

  Alkylation of cyclic ketones and α-methoxycarbonyl ketones with 4-iodo-2-trimethylstannylbut-1-ene and/or 5-iodo-2-trimethylstannylpent-1-ene, and subsequent (Ph3P)4Pd-catalysed cyclization of the enol trifluoromethanesulphonates derived form the alkylation products, from the basis of new annulation sequences which result in the formation of diene systems.

  环酮和α-甲氧基羰基酮与4-碘-2-三甲基锡烷基丁-1-烯和/或5-碘-2-三甲基锡烷基戊-1-烯的烷基化反应，以及随后的（Ph 3 P）4 Pd催化的环化反应烯醇三氟甲烷磺酸酯是根据新的环化顺序而形成的烷基化产物，该环化导致形成二烯系统。
• Structure–Activity Relationship and in Vitro and in Vivo Evaluation of the Potent Cytotoxic Anti-microtubule Agent <i>N</i>-(4-Methoxyphenyl)-<i>N</i>,2,6-trimethyl-6,7-dihydro-5<i>H</i>-cyclopenta[<i>d</i>]pyrimidin-4-aminium Chloride and Its Analogues As Antitumor Agents
  作者：Aleem Gangjee、Ying Zhao、Sudhir Raghavan、Cristina C. Rohena、Susan L. Mooberry、Ernest Hamel

  DOI：10.1021/jm400639z

  日期：2013.9.12

  A series of 21 substituted cyclopenta[d]pyrimidines were synthesized as an extension of our discovery of the parent compound (+/-)-1 center dot HCl as an anti-microtubule agent. The structure activity relationship indicates that the N-methyl and a 4N-methoxy groups appear important for potent activity. In addition, the 6-substituent in the parent analogue is not necessary for activity. The most potent compound 30. HCl was a one to two digit nanomolar inhibitor of most tumor cell proliferations and was up to 7-fold more potent than the parent compound (+/-)-1 center dot HCl. In addition, 30 center dot HCl inhibited cancer cell proliferation regardless of Pgp or beta III-tubulin status, both of which are known to cause clinical resistance to several antitubulin agents. In vivo efficacy of 30 center dot HCl was demonstrated against a triple negative breast cancer xenograft mouse model. Compound 30 center dot HCl is water-soluble and easily synthesized and serves as a lead compound for further preclinical evaluation as an