ethyl 4-cyclohexyl-2-oxo-butyrate | 95779-66-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 4-cyclohexyl-2-oxo-butyrate
• 英文别名: ethyl 4-cyclohexyl-2-ketobutanoate；ethyl 4-cyclohexyl-2-oxobutanoate；ethyl 2-oxo-4-cyclohexylbutyrate；ethyl 2-oxo-4-cyclohexylbutylate；ethyl 4-cyclohexyl-2-oxobutyrate
• CAS: 95779-66-1
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: FKGBXCDWKAFEPH-UHFFFAOYSA-N

物化性质

• 沸点：
  301.2±11.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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 4-cyclohexyl-2-oxo-butyrate 在 palladium on activated charcoal sodium hydroxide 、 {bis[(4R,5S)-di-Ph-oxazoline-2-yl]methane}Cu(OTf)2 、 氢气 、 L-Selectride 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 丙酮 、 甲苯 为溶剂， 反应 19.25h， 生成 (4S,5R)-4-环己基甲基-2-恶唑烷酮-5-羧酸甲酯
  参考文献：
  名称：

  Catalytic Asymmetric Direct α-Amination Reactions of 2-Keto Esters:  A Simple Synthetic Approach to Optically Active syn-β-Amino-α-hydroxy Esters

  摘要：

  The catalytic enantioselective direct alpha-amination reaction of 2-keto esters with easily available azo dicarboxylates as the nitrogen source and chiral bisoxazoline-copper(II) complexes as the catalyst is presented. The reactions proceed with excellent enantioselectivities and high yields. The scope of the reaction is demonstrated by the direct amination of a series of 2-keto esters having different substituent patterns. The reaction provides an easy catalytic route to optically active syn-beta-amino-alpha-hydroxy esters, as demonstrated for the synthesis of masked syn-beta-amino-alpha-hydroxy esters (as oxazolidinones) and N-Boc-syn-beta-amino-alpha-hydroxy esters. On the basis of the absolute configuration of the products a tentative model for the transition state is suggested.

  DOI：

  10.1021/ja0175486
• 作为产物：
  描述：

  3-环己基丙烯酸乙酯 在 palladium on activated charcoal 硫酸 、 氢气 、 sodium ethanolate 、 sodium chloride 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 ethyl 4-cyclohexyl-2-oxo-butyrate
  参考文献：
  名称：

  Synthesis and angiotensin converting enzyme inhibitory activity of 1,5-benzothiazepine and 1,5-benzoxazepine derivatives. I.

  摘要：

  新型血管紧张素转化酶（ACE）抑制剂的设计与合成，包括(R)-3-氨基-4-氧代-2, 3, 4, 5-四氢-1, 5-苯硫氮杂环-5-乙酸（7, 26, 33 和 37）以及(S)-3-氨基-4-氧代-2, 3, 4, 5-四氢-1, 5-苯氧氮杂环-5-乙酸（8 和 27），本文进行了描述。这些系列中的一些化合物在体外和体内显示出强烈的ACE抑制活性。同时讨论了结构-活性关系。

  DOI：

  10.1248/cpb.34.1128

文献信息

• BrF₃, an Underutilized Reagent in Organic Chemistry:  A Novel C−C−N to C−N−C Rearrangement
  作者：Shlomo Rozen、Iris Ben-David

  DOI：10.1021/jo0013094

  日期：2001.1.1

  bromine trifluoride in organic chemistry. Under the right conditions, it can be a useful tool and generate a new and unprecedented chemistry. Thus, when reacted with oxime methyl ethers of alpha-ketoesters, BrF3 was able to convert the oxime group into a CF2 group and through a new type of rearrangement cause a shift of the carboxylate group to the nitrogen atom. The novel structure of the alpha,alpha-difluorocarbamate

  对于有机化学中的三氟化溴知之甚少。在适当的条件下，它可以成为有用的工具，并产生新的和前所未有的化学反应。因此，当与α-酮酸酯的肟甲基醚反应时，BrF3能够将肟基转化为CF2基，并通过新型的重排导致羧酸酯基向氮原子的转移。如化合物3、8、9、12、15和18所示，α，α-二氟氨基甲酸酯的新颖结构也通过15N NMR证实。在形成19时观察到另一种新颖的“双重排”。动态19F NMR实验表明，这些新型氨基甲酸酯的氮反转-旋转（NIR）障碍较高，约为12.5 kcal / mol。
• 3-Amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04548932A1

  公开（公告）日：1985-10-22

  Novel 3-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine derivatives of the formula ##STR1## [wherein R.sup.1 and R.sup.2 are independently hydrogen, halogen, trifluoromethyl, lower alkyl or lower alkoxy, or both jointly form tri- or tetramethylene; R.sup.3 is hydrogen, optionally substituted lower alkyl or optionally substituted aralkyl; R.sup.4 is hydrogen, optionally substituted alkyl, optionally substituted aralkyl or optionally substituted cycloalkylalkyl; Y is a carboxyl group which may be esterified or amidated; m is 1 or 2] and salts thereof. These compounds and salts thereof exhibits inhibitory activity on angiotensin converting enzyme and so forth, and are of value as an agent for diagnosis, prevention and treatment of circulatory diseases (e.g. hypertension, cardiopathy, cerebral apoploxy).

  新颖的3-氨基-4-酮基-2,3,4,5-四氢-1,5-苯并噁唑啉衍生物的化学式为##STR1##[其中R.sup.1和R.sup.2独立地为氢、卤素、三氟甲基、低碳烷基或低碳氧基，或者共同形成三元或四元亚甲基；R.sup.3为氢、可选择取代的低碳烷基或可选择取代的芳基烷基；R.sup.4为氢、可选择取代的烷基、可选择取代的芳基烷基或可选择取代的环烷基烷基；Y为可酯化或酰胺化的羧基；m为1或2]及其盐。这些化合物及其盐对肾素转换酶等具有抑制活性，可作为循环系统疾病（如高血压、心脏病、脑卒中）的诊断、预防和治疗药物。
• Direct catalytic asymmetric aldol reactions of pyruvates: scope and mechanism
  作者：Nicholas Gathergood、Karsten Juhl、Thomas B. Poulsen、Karl Thordrup、Karl Anker Jørgensen

  DOI：10.1039/b316092k

  日期：——

  different chiral Lewis acids as the catalyst, amines, ratios of chiral bisoxazoline copper(II) salts:amine, and solvents gave up to 96% ee of the isotetronic acid. Then the reaction was extended to a cross-aldol reaction of various 2-ketoesters with activated carbonyl compounds to give the cross-aldol adduct with excellent enantiomeric excess. Furthermore, the synthesis of the isotetronic acids was investigated

  研究了手性双恶唑啉铜（II）配合物催化的2-酮酸酯的直接羟醛反应。首先，报道了丙酮酸乙酯的直接均醛醇缩合反应，该反应进行后得到2-羟基-2-甲基-4-氧代戊二酸二乙酯。将其分离为更稳定的旋光性异二十二酸，收率好，在不存在碱（如胺）的情况下对映体过量。使用不同的手性路易斯酸作为催化剂，胺，手性双恶唑啉铜（II）盐：胺的比例和溶剂的详细研究得出了等渗酸的96％ee。然后将反应扩展至各种2-酮酯与活化的羰基化合物的交叉醇醛缩合反应，得到具有优异对映体过量的交叉醇醛加合物。此外，从这些交叉的羟醛加合物研究了等渗酸的合成，从而提供了有关羟醛反应过程中立体异构中心形成的重要信息。基于高羟醛加合物的绝对构型，讨论了高羟醛反应的机理。
• Condensed, seven-membered ring compounds and their use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04564612A1

  公开（公告）日：1986-01-14

  Novel condensed, seven-membered ring compounds of the formula: ##STR1## [wherein R.sup.1 and R.sup.2 each represent hydrogen, halogen, trifluoromethyl, lower alkyl or alkoxy, or both jointly form tri- or tetramethylene; R.sup.3 is hydrogen, lower alkyl or aralkyl; R.sup.4 is hydrogen or alkyl, aralkyl or cycloalkylalkyl which may be substituted; X is a group represented by the formula S(O).sub.n (where n is an integer of 0 to 2); Y is a carboxyl group which may be esterified or amidated; m is 1 or 2] and salts thereof. These compounds exhibit inhibitory activity on angiotensin converting enzyme and so forth, and are of value as an agent for diagnosis, prevention and treatment of hypertension.

  小说简化，式子为：##STR1##[其中R.sup.1和R.sup.2分别代表氢，卤素，三氟甲基，低烷基或烷氧基，或共同形成三元或四元亚甲基; R.sup.3是氢，低烷基或芳基烷基; R.sup.4是氢或烷基，芳基烷基或环烷基烷基，可以被取代; X是由式S(O).sub.n（其中n是0到2的整数）表示的基团; Y是羧基，可以酯化或酰胺化; m为1或2]及其盐。这些化合物表现出对血管紧张素转化酶等的抑制活性，因此在高血压的诊断、预防和治疗中具有价值。
• 3-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04591458A1

  公开（公告）日：1986-05-27

  Novel 3-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine derivatives of the formula ##STR1## [wherein R.sup.1 and R.sup.2 are independently hydrogen, halogen trifluoromethyl, lower alkyl or lower alkoxy, or both jointly form tri- or tetramethylene; R.sup.3 is hydrogen, optionally substituted lower alkyl or optionally substituted aralkyl; R.sup.4 is hydrogen, optionally substituted alkyl, optionally substituted aralkyl or optionally substituted cycloalkylalkyl; Y is a carboxyl group which may be esterified or amidated; m is 1 or 2] and salts thereof. These compounds and salts thereof exhibits inhibitory activity on angiotensin converting enzyme and so forth, and are of value as an agent for diagnosis, prevention and treatment of circulatory diseases (e.g. hypertension, cardiopathy, cerebral apoploxy).

  化合物和盐的新颖3-氨基-4-氧代-2,3,4,5-四氢-1,5-苯并噁唑衍生物的公式为##STR1##[其中R.sup.1和R.sup.2独立地为氢，卤素三氟甲基，低级烷基或低级烷氧基，或共同形成三亚甲基或四亚甲基; R.sup.3为氢，可选择取代的低级烷基或可选择取代的芳基烷基; R.sup.4为氢，可选择取代的烷基，可选择取代的芳基烷基或可选择取代的环烷基烷基; Y为可酯化或酰胺化的羧基; m为1或2]。这些化合物及其盐表现出对血管紧张素转换酶等的抑制活性，并具有作为循环疾病（如高血压，心脏病，脑卒中）的诊断，预防和治疗剂的价值。