3-(1-methyl-2-oxocyclohexyl)propanenitrile | 144126-65-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(1-methyl-2-oxocyclohexyl)propanenitrile
• CAS: 144126-65-8
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: DBHUNYNZTIQTNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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-(1-methyl-2-oxocyclohexyl)propanenitrile 在 lithium aluminium tetrahydride 、 四乙基对甲苯磺酸铵 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 1.0h， 生成 (3aS,7aR)-3a-methyl-2,3,4,5,6,7-hexahydro-1H-indene-1,7a-diol
  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
• 作为产物：
  描述：

  2-甲基环己酮 、 丙烯腈 在 四丁基氢氧化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以30%的产率得到3-(1-methyl-2-oxocyclohexyl)propanenitrile
  参考文献：
  名称：

  在电子合成系统中利用膜交换离子。：V.固态电子琴中的michael induites的添加物。

  摘要：

  可以通过在多孔阴极和固体聚合物电解质之间的界面上在不存在支持电解质的情况下在质子惰性介质中电生成的碱来引发向丙烯腈或酰化甲酯中的碳酸的添加。电力消耗低于每摩尔法拉第10 -2法拉第。将酸度降低的供体（2-硝基丙烷，丙二腈，丙二酸二乙酯，氰基乙酸乙酯，2-甲基环己酮，芴）置于酸性下，可以估算在这种界面上可以达到的碱性水平。研究了不同因素（例如离子交换膜的性质，膜第二面的碱性，碱的存在）对反应速率和产率的影响。

  DOI：

  10.1016/s0040-4020(01)87706-1

文献信息

• Construction of Functionalized Carbocycles Having Contiguous Tertiary Carbinol and All-Carbon Stereogenic Centers
  作者：Chennakesava Reddy、Srinivasarao Arulananda Babu、Nayyar Ahmad Aslam、Vadla Rajkumar

  DOI：10.1002/ejoc.201201382

  日期：2013.4

  A highly stereoselective protocol is reported for customizing functionalized carbocyclic building blocks (β-hydroxy esters) and bicyclic lactones with a stereoarray that contains contiguous tertiary carbinol and all-carbon stereocenters. The efficient asymmetric induction and diastereofacial selective addition of allyl and propargyl indiums to hindered α,α-disubstituted cycloalkanones is presented

  报告了一种高度立体选择性的协议，用于定制功能化碳环结构单元（β-羟基酯）和双环内酯，其立体阵列包含连续的叔甲醇和全碳立体中心。介绍了烯丙基和炔丙基铟与受阻 α,α-二取代环烷酮的有效不对称诱导和非对映选择性加成。代表性产物的立体化学是从单晶 X 射线晶体结构分析中明确建立的，并提出了一种合理的反应途径来支持高非对映面选择性。
• CYCLIC AMIDE DERIVATIVES AS INHIBITORS OF 11 - BETA - HYDROXYSTEROID DEHYDROGENASE AND USES THEREOF
  申请人：CONNEXIOS LIFE SCIENCES PVT. LTD.

  公开号：US20150158860A1

  公开（公告）日：2015-06-11

  The present invention relates to certain amide derivatives that have the ability to inhibit 11-β-hydroxysteroid dehydrogenase type 1 (11β-HSD-1) and which are therefore useful in the treatment of certain disorders that can be prevented or treated by inhibition of this enzyme. In addition the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders. It is expected that the compounds of the invention will find application in the treatment of conditions such as non-insulin dependent type 2 diabetes mellitus (NIDDM), insulin resistance, obesity, impaired fasting glucose, impaired glucose tolerance, lipid disorders such as dyslipidemia, hypertension and as well as other diseases and conditions.

  本发明涉及某些酰胺衍生物，这些衍生物具有抑制11-β-羟基类固醇脱氢酶1型（11β-HSD-1）的能力，因此在预防和治疗可以通过抑制该酶来预防或治疗的某些疾病中是有用的。此外，发明还涉及这些化合物的制备方法、含有这些化合物的药物组合物以及这些化合物在治疗某些疾病中的用途。预计本发明的化合物将在治疗非胰岛素依赖型2型糖尿病（NIDDM）、胰岛素抵抗、肥胖、空腹血糖受损、葡萄糖耐量受损、脂质紊乱（如血脂异常）、高血压以及其他疾病和状况中找到应用。
• Indium-assisted aluminium-based stereoselective allylation of prostereogenic α,α-disubstituted cycloalkanones and imines
  作者：Chennakesava Reddy、Srinivasarao Arulananda Babu、Nayyar Ahmad Aslam

  DOI：10.1039/c4ra04293j

  日期：——

  Al0 for the allylation of a variety of prostereogenic α,α-disubstituted (hindered) cycloalkanones, 1,2-dione-based systems and various imino systems (CN functional groups) is reported. The stereoselective InCl3-catalyzed Al-based allylation of various 2-substituted-2-carbethoxycycloalkanones gave the corresponding products with moderate to excellent diastereoselectivity. The allylation and propargylation

  催化量的InCl 3和Al 0的组合用于烯丙基化各种促成α，α-二取代（受阻）的环烷酮，1,2-二酮基体系和各种亚氨基体系（C N官能团）的烯丙基化被报道。各种2-取代的-2-碳乙氧基环烷酮的立体选择性InCl 3催化的基于Al的烯丙基化，给出了具有中等至优异的非对映选择性的相应产物。使用催化量的InCl 3与Al 0结合使用，使包括α-亚氨基酯在内的亚胺的烯丙基化和炔丙基化得到中等至良好收率的相应的烯丙基化和炔丙基化化合物。如果将γ-取代的烯丙基卤化物添加到亚氨基化合物中，则获得低至非常好的非对映选择性。手性N-叔丁基亚磺酰基亚胺系统的烯丙基化以中等收率提供了相应的产物，具有良好或优异的非对映选择性。
• [EN] CYCLIC AMIDE DERIVATIVES AS INHIBITORS OF 11 - BETA - HYDROXYSTEROID DEHYDROGENASE AND USES THEREOF<br/>[FR] DÉRIVÉS D'AMIDE CYCLIQUES À UTILISER EN TANT QU'INHIBITEURS DE 11-BÊTA-HYDROXYSTÉROÏDE DÉSHYDROGÉNASE ET UTILISATIONS DE CEUX-CI
  申请人：CONNEXIOS LIFE SCIENCES PVT LTD

  公开号：WO2013128465A1

  公开（公告）日：2013-09-06

  The present invention relates to certain amide derivatives that have the ability to inhibit 11-β-hydroxysteroid dehydrogenase type 1 (11β-HSD-1) and which are therefore useful in the treatment of certain disorders that can be prevented or treated by inhibition of this enzyme. In addition the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders. It is expected that the compounds of the invention will find application in the treatment of conditions such as non-insulin dependent type 2 diabetes mellitus (NIDDM), insulin resistance, obesity, impaired fasting glucose, impaired glucose tolerance, lipid disorders such as dyslipidemia, hypertension and as well as other diseases and conditions.

  本发明涉及某些酰胺衍生物，这些衍生物具有抑制11-β-羟基类固醇脱氢酶1型（11β-HSD-1）的能力，因此在预防或治疗可通过抑制该酶来预防或治疗的某些疾病中是有用的。此外，本发明还涉及这些化合物的制备方法、含有这些化合物的药物组合物以及这些化合物在治疗某些疾病中的用途。预计本发明的化合物将用于治疗非胰岛素依赖型2型糖尿病（NIDDM）、胰岛素抵抗、肥胖、空腹血糖受损、葡萄糖耐量受损、脂质紊乱（如血脂异常）、高血压以及其它疾病和状况。
• Ruthenium-catalyzed hydration of nitriles and transformation of δ-ketonitriles to ene-lactams: total synthesis of (−)-pumiliotoxin C
  作者：Shun-Ichi Murahashi、Shigehiro Sasao、Eiichiro Saito、Takeshi Naota

  DOI：10.1016/s0040-4020(01)81902-5

  日期：1993.1

  1–2 equivalents of water can be performed efficiently by using RuH2(PPh3)4 catalyst to give the corresponding amides. Under the similar reaction conditions, δ-ketonitriles can be converted into the corresponding ene-lactams, which are versatile synthetic intermediates. The efficiency of the reaction is demonstrated by the short-step synthesis of (−)-pumiliotoxin C.

  通过使用RuH 2（PPh 3）4催化剂生成相应的酰胺，可以有效地用1-2当量的水进行腈水合。在相似的反应条件下，δ-乙腈可以转化为相应的烯-内酰胺，它们是通用的合成中间体。通过（-）-pumiliotoxin C的短步合成证明了反应的效率。