methyl 4-oxocyclohex-2-enecarboxylate | 67201-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-oxocyclohex-2-enecarboxylate
• 英文别名: methyl 4-oxocyclohex-2-ene-1-carboxylate
• CAS: 67201-30-3
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: UVDNBPZBGMVZBV-UHFFFAOYSA-N

物化性质

• 沸点：
  242.5±40.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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 4-oxocyclohex-2-enecarboxylate 在 2Cs⁽¹⁺⁾*CO₃^(2-)*2H₂O=Cs₂CO₃*2H₂O 、 palladium 10% on activated carbon 、 氢气 、 sodium hexamethyldisilazane 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 20.03h， 生成 methyl 7-(ethoxycarbonylmethyl)-4,5,6,7-tetrahydro-2H-isoindole-4-carboxylate
  参考文献：
  名称：

  Synthesis of 3,4-fused cycloalkanopyrroles by 1,3-dipolar cycloaddition

  摘要：

  The synthesis of a number of 3,4-fused cycloalkanopyrroles bearing substituents on the cycloalkane ring was accomplished by 1,3-dipolar cycloaddition. The yield of the cyclization appeared to depend on the base-sensitivity of the Michael acceptor, but the method is applicable across a broad range of cyclic alpha,beta-unsaturated ketone esters. Functional group transformations can be undertaken following pyrrole synthesis to increase the diversity of cycloalkanopyrroles accessible by this method. One pyrrole thus made is a diester of a conformationally-constrained analogue of porphobilinogen, the precursor of the natural tetrapyrroles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.013
• 作为产物：
  描述：

  4-(tert-Butyl-dimethyl-silanyloxy)-3-p-tolylsulfanyl-cyclohex-3-enecarboxylic acid methyl ester 在 sodium periodate 、 magnesium bromide 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 生成 methyl 4-oxocyclohex-2-enecarboxylate
  参考文献：
  名称：

  3-(对甲苯硫基)-2-(三甲基甲硅烷氧基)-1,3-丁二烯的简单合成和Diels-Alder反应

  摘要：

  在二异丙基乙胺的存在下，3-(对甲苯基亚磺酰基)-2-丁酮与三氟甲磺酸三甲基甲硅烷基酯的反应定量地得到3-(对甲苯基硫基)-2-(三甲基甲硅烷氧基)-1,3-丁二烯(2)。研究了 2 和相关二烯与丙烯酸甲酯的 Diels-Alder 反应。

  DOI：

  10.1246/cl.1991.1577

文献信息

• C-3 CYCLOALKENYL TRITERPENOIDS WITH HIV MATURATION INHIBITORY ACTIVITY
  申请人：Bristol-Myers Squibb Company

  公开号：US20130210787A1

  公开（公告）日：2013-08-15

  Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, C-3 cycloalkenyl triterpenoids that possess unique antiviral activity are provided as HIV maturation inhibitors, as represented by compounds of Formulas I, II, III and IV: wherein X can be a C 4-8 cycloalkyl, C 4-8 cycloalkenyl, C 4-9 spirocycloalkyl, C 4-9 spirocycloalkenyl, C 4-8 oxacycloalkyl, C 4-8 dioxacycloalkyl, C 6-8 oxacycloalkenyl, C 6-8 dioxacycloalkenyl, C 6-9 oxaspirocycloalkyl, or C 6-9 oxaspirocycloalkenyl ring. These compounds are useful for the treatment of HIV and AIDS.

  具有药物和生物活性的化合物、其药物组合物及其用途被详细说明。特别是，提供了具有独特抗病毒活性的C-3环烯三萜类化合物，作为HIV成熟抑制剂，由公式I、II、III和IV所示的化合物代表： 其中X可以是C4-8环烷基，C4-8环烯基，C4-9螺环烷基，C4-9螺环烯基，C4-8氧杂环烷基，C4-8二氧杂环烷基，C6-8氧杂环烯基，C6-8二氧杂环烯基，C6-9氧杂螺环烷基或C6-9氧杂螺环烯基环。这些化合物用于治疗HIV和艾滋病。
• [EN] DIAZENIUMDIOLATE CYCLOHEXYL DERIVATIVES<br/>[FR] DÉRIVÉS CYCLOHEXYLIQUES DE DIOLATE DE DIAZÉNIUM
  申请人：MERCK SHARP & DOHME

  公开号：WO2011146371A1

  公开（公告）日：2011-11-24

  A compound having the structure (I) or a pharmaceutically acceptable salt thereof, wherein R3 is hydrogen, deuterium, -OH, -OC1-6alkyl, or halogen; R8 is hydrogen, deuterium, or C1-6alkyl; R11 and R12 are independently hydrogen, -C1-6alkyl, -OH, -OC1-6alkyl, or halogen; R13 and R14 are independently -C1-6alkyl, -(CH2)1-2OH, or -OC1-6alkyl, or, together with the nitrogen atom to which they are attached, form a 4- to 7-membered heterocyclic ring containing one nitrogen atom and 0 or 1 oxygen atoms, wherein said ring is unsubstituted or mono-, di- or tri-substituted with halogen or -C1-6alkyl; R15 is (CR1R2)nC(O)OR16, wherein n is 0, 1 or 2, -C(O)NHCH(R17)OR16, or -C(O)NHCH(R17)C(O)NHCH(R18)C(O)OR16; R16 is hydrogen, C1-6alkyl, or (CH2)1-2N+R19R20R21; R1, R2, R4, R5, R6, R7, R9, R10, R17, R18, R19, R20, and R21 are independently hydrogen or -C1-6alkyl; and stereoisomers thereof, and pharmaceutically acceptable salts thereof, and pharmaceutically acceptable salts of stereoisomers thereof.

  化合物具有结构（I）或其药学上可接受的盐，其中R3是氢，氘，-OH，-OC1-6烷基或卤素；R8是氢，氘或C1-6烷基；R11和R12独立地是氢，-C1-6烷基，-OH，-OC1-6烷基或卤素；R13和R14独立地是-C1-6烷基，-(CH2)1-2OH或-OC1-6烷基，或者与它们连接的氮原子一起形成一个含有一个氮原子和0或1个氧原子的4-至7-成员杂环环，其中所述环未取代或单取代，双取代或三取代为卤素或-C1-6烷基；R15是（CR1R2）nC（O）OR16，其中n为0，1或2，-C（O）NHCH（R17）OR16，或-C（O）NHCH（R17）C（O）NHCH（R18）C（O）OR16；R16是氢，C1-6烷基或（CH2）1-2N+R19R20R21；R1，R2，R4，R5，R6，R7，R9，R10，R17，R18，R19，R20和R21独立地是氢或-C1-6烷基；以及其立体异构体，及其药学上可接受的盐，以及其立体异构体的药学上可接受的盐。
• The Domino Oxa-Michael Addition–Aldol Reaction: Access to Variably Substituted Tetrahydroxanthenones
  作者：Ulrike K. Ohnemüller (née Schmid)、Carl F. Nising、Martin Nieger、Stefan Bräse

  DOI：10.1002/ejoc.200500887

  日期：2006.3

  Tetrahydroxanthenones represent the core of many natural products, most of which exhibit interesting biological activities. In the course of our synthetic efforts towards the total synthesis of the secalonic acids, which contain two of these tricyclic units, we have investigated the influence of substituents on the one-step domino oxa-Michael addition–aldol reaction leading to tetrahydroxanthenones

  四氢氧杂蒽酮代表了许多天然产物的核心，其中大部分表现出有趣的生物活性。在我们对含有两个三环单元的癸二酸进行全合成的过程中，我们研究了取代基对一步多米诺氧杂-迈克尔加成-羟醛反应导致四氢氧杂蒽酮的影响。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Biosynthetic studies on ansatrienin A. Formation of the cyclohexanecarboxylic acid moiety
  作者：Bradley S. Moore、Hyeongjin Cho、Rosangela Casati、Eileen Kennedy、Kevin A. Reynolds、Ursula Mocek、John M. Beale、Heinz G. Floss

  DOI：10.1021/ja00065a042

  日期：1993.6

  biosynthesis of ansatrienin (mycotrienin) has been studied. [sup 13]C- and [sup 2]H-labeled samples of shikimic acid were used to probe the stereochemistry of processing the cyclohexane ring of shikimic acid and to establish the fate of all the precursor hydrogens in this transformation. A sample of [2-[sup 13]C]shikimic acid was fed to Streptomyces collinus Tu 1982, and [sup 13]C in the resulting ansatrienin

  环己烷甲酸部分在 ansatrienin (mycotrienin) 的生物合成中的形成已被研究。[sup 13]C-和[sup 2]H-标记的莽草酸样品用于探测处理莽草酸环己烷环的立体化学，并确定该转化中所有前体氢的命运。[2-[sup 13]C]莽草酸样品被加入 Streptomyces collinus Tu 1982，发现所得 ansatrienin 中的 [sup 13]C 仅位于 C-36。在 Ansatrienin 的生物合成样品的水解中，伴随环己烷甲酸的 1-环己烯甲酸在 C-2 处而不是在 C-6 处带有 [sup 13] C 标记。[2-[sup 2]H]-、[3-[sup 2]H]-、[4-[sup 2]H]、[2,5-[sup 2]H[sub 2]]-的样本, [2,3,4,5-[sup 2]H[sub 4]]-, 和[6-[sup 2]H[sub 1]]莽草酸被喂给S
• Synthesis of 4-Aminocyclohex-1-enecarboxylates from Danishefsky's Diene
  作者：Josefina Quirante、Xavier Vila、Josep Bonjoch

  DOI：10.1055/s-2001-17706

  日期：——

  An efficient BF3·Et2O mediated conversion of Diels-Alder adduct 1 of Danishefsky’s diene and methyl acrylate yielded cyclohexenones 2 and 3. Subsequent reductive amination with several amines using NaBH(OAc)3 in acetic acid medium gave 4-alkylaminocyclohex-1-enecarboxylate derivatives (4a-e) in a concise form.

  通过BF3·Et2O介导的高效转化，Danishefsky二烯与甲基丙烯酸甲酯的Diels-Alder加合物1生成了环己烯酮2和3。随后，在乙酸介质中使用NaBH(OAc)3进行还原胺化反应，与多种胺反应，简洁地合成了4-烷基氨基环己-1-烯羧酸酯衍生物（4a-e）。