ethyl 3-(3-butenyl)-2-oxocyclohexanecarboxylate | 127230-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-(3-butenyl)-2-oxocyclohexanecarboxylate
• 英文别名: ethyl 3-(but-3'-enyl)-2-oxocyclohexane-1-carboxylate；3-but-3-enyl-2-oxo-cyclohexanecarboxylic acid ethyl ester；Opt.-inakt. 2-Oxo-3-(buten-(3)-yl)-cyclohexan-carbonsaeure-(1)-aethylester；3-But-3-enyl-2-oxo-cyclohexancarbonsaeure-aethylester；Ethyl 3-(but-3-en-1-yl)-2-oxocyclohexane-1-carboxylate；ethyl 3-but-3-enyl-2-oxocyclohexane-1-carboxylate
• CAS: 127230-66-4
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: NBWDGGPAJJEMLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  ethyl 3-(3-butenyl)-2-oxocyclohexanecarboxylate 在 sodium hydroxide 、 三甲基氯硅烷 、 叠氮磷酸二苯酯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 88.5h， 生成
  参考文献：
  名称：

  Selective Inhibitors of the Serine Protease Plasmin:  Probing the S3 and S3‘ Subsites Using a Combinatorial Library

  摘要：

  A combinatorial library of 400 serine protease inhibitors with the general structure Cbz-X-aa-Trp-cyclohexanone-Trp-Y-aa-OH has been constructed. The library was synthesized on the solid phase using mix-and-split synthesis, where 20 different amino acids were incorporated at both the X-aa and Y-aa positions. These two positions correspond to the S3 and S3' subsites of the active site. Iterative deconvolution was used to identify hits from the library. The library was screened against four serine proteases: plasmin, kallikrein, thrombin, and trypsin. Seven inhibitors from the library that showed promising activities were resynthesized using solutionphase methods. Four of these compounds were good inhibitors of plasmin with IC50 values in the range of 2.7 - 3.6 mu M. The most potent of these inhibitors showed > 150-fold selectivity for plasmin when compared to the other three serine proteases.

  DOI：

  10.1021/jm050488k
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium 、 Petroleum ether 作用下， 生成 ethyl 3-(3-butenyl)-2-oxocyclohexanecarboxylate
  参考文献：
  名称：

  112.熔融碳环。第七部分 由不饱和叔醇制备环状烃。顺式-9-甲基-八氢萘和-十氢萘的合成以及角甲基的存在的证明

  摘要：

  DOI：

  10.1039/jr9360000470

文献信息

• Synthesis of ABE tricyclic analogues of methyllycaconitine using a Wacker oxidation–aldol strategy to append the B ring to the AE fragment
  作者：David Barker、Margaret A. Brimble、Malcolm McLeod、G. Paul Savage、David J. Wong

  DOI：10.1039/b200073n

  日期：2002.3.25

  conversion of the C-9 ketone 10 to vinyl ether 6. Wittig methylenation of ketone 10 afforded diene 7, however, subsequent attempts to effect double hydroboration–oxidation of diene 7 failed to realise diol 11enroute to the key dialdehyde precursor 5 required for the McMurray coupling. Wacker oxidation of the homoallyl group of 10 afforded methyl ketone 12 which underwent intramolecular aldol condensation to

  描述了生物碱甲基lycaconitine 1的ABE三环类似物18的合成。所述类似物含有的关键药效据说是负责甲基牛的生物活性1，即，从叔形成的homocholine基序ñ -乙胺在3-氮杂双环[3.3.1]壬烷环系统和2-（3- 2，5-二氧杂吡咯啉-1-基）苯甲酸甲酯酯侧链。3-氮杂双环[3.3.1]壬烷环系统10是通过3-（but-3'-烯基）-2-氧代环己烷-1-甲酸乙酯9与乙胺和甲醛的双重曼尼希反应组装的。尝试到B环追加到此AE环系经由二醛5的McMurray偶联因无法将C-9酮10转化为乙烯基醚6而受阻。维悌希酮的亚甲基化10，得到二烯7，但是，二烯的后续尝试效果双硼氢化-氧化7未能实现二醇11连接路由到密钥二醛前体5为麦克莫里耦合必需的。Wacker氧化10个均烯丙基基团后得到的甲基酮12，经过分子内羟醛缩合形成烯酮13。酮选择性还原并甲基化后，所得甲基醚15 进行酯侧链还原，
• Manganese(III)-based oxidative free-radical cyclization of unsaturated .beta.-keto esters, 1,3-diketones, and malonate diesters
  作者：Steven A. Kates、Mark A. Dombroski、Barry B. Snider

  DOI：10.1021/jo00295a035

  日期：1990.4
• KATES, STEVEN A.;DOMBROSKI, MARK A.;SNIDER, BARRY B., J. ORG. CHEM., 55,(1990) N, C. 2427-2436
  作者：KATES, STEVEN A.、DOMBROSKI, MARK A.、SNIDER, BARRY B.

  DOI：——

  日期：——
• Selective Inhibitors of the Serine Protease Plasmin:  Probing the S3 and S3‘ Subsites Using a Combinatorial Library
  作者：Fengtian Xue、Christopher T. Seto

  DOI：10.1021/jm050488k

  日期：2005.11.1

  A combinatorial library of 400 serine protease inhibitors with the general structure Cbz-X-aa-Trp-cyclohexanone-Trp-Y-aa-OH has been constructed. The library was synthesized on the solid phase using mix-and-split synthesis, where 20 different amino acids were incorporated at both the X-aa and Y-aa positions. These two positions correspond to the S3 and S3' subsites of the active site. Iterative deconvolution was used to identify hits from the library. The library was screened against four serine proteases: plasmin, kallikrein, thrombin, and trypsin. Seven inhibitors from the library that showed promising activities were resynthesized using solutionphase methods. Four of these compounds were good inhibitors of plasmin with IC50 values in the range of 2.7 - 3.6 mu M. The most potent of these inhibitors showed > 150-fold selectivity for plasmin when compared to the other three serine proteases.
• 112. Fused carbon rings. Part VII. The preparation of cyclic hydrocarbons from unsaturated tertiary alcohols. The synthesis of cis-9-methyl-octalin and -decalin, and a proof of the presence of the angular methyl group
  作者：D. C. Hibbit、R. P. Linstead

  DOI：10.1039/jr9360000470

  日期：——