methyl 5-oxo-1-cyclohexenecarboxylate | 66838-90-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-oxo-1-cyclohexenecarboxylate
• 英文别名: methyl 5-oxocyclohexene-1-carboxylate
• CAS: 66838-90-2
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: WRAIXZFSBWOUSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 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 5-oxo-1-cyclohexenecarboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 3-氧代环己烯-1-羧酸甲酯
  参考文献：
  名称：

  Control of the Birch Reduction ofm-Anisic Acid to Produce Specific 3-Oxocyclohexenecarboxylic Acids

  摘要：

  据报道，有一种高效的方法可以通过桦木还原法从间苯二甲酸（3）中合成相对大量的 3-氧代-1-环己烯羧酸甲酯（2b），这是一种有用的亲二烯化合物和光试剂。 根据所选条件，用液氨中的锂处理 3，可产生四种特定 3-氧代环己烯羧酸中的任何一种。

  DOI：

  10.1055/s-1987-28124
• 作为产物：
  描述：

  3-methoxycyclohexa-1,4-diene-1-carboxylic acid 在 草酸 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 32.0h， 生成 methyl 5-oxo-1-cyclohexenecarboxylate
  参考文献：
  名称：

  [EN] THERAPEUTIC COMPOUNDS AND METHODS
  [FR] COMPOSÉS ET MÉTHODES THÉRAPEUTIQUES

  摘要：

  The disclosure provides a compound of formula I: or a salt thereof, wherein R1, R2, R4, L1, L2, and A have any of the values described in the specification, as well as compositions comprising a compound of formula (I). The compounds 5 are useful as TRPV4 antagonists.

  公开号：

  WO2024011214A1

文献信息

• 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
• Cathepsin cysteine protease inhibitors
  申请人：Bayly Christopher

  公开号：US20070167635A1

  公开（公告）日：2007-07-19

  This invention relates to a class of compounds having the general formula (I) which are cysteine protease inhibitors, including but not limited to, inhibitors of cathepsins K, L, S and B. These compounds are useful for treating diseases in which inhibition of bone resorption is indicated, such as osteoporosis.

  本发明涉及一类具有通式(I)的化合物，它们是半胱氨酸蛋白酶抑制剂，包括但不限于对卡特普西林K、L、S和B的抑制剂。这些化合物可用于治疗需要抑制骨吸收的疾病，例如骨质疏松症。
• Diastereofacial selectivity of Diels-Alder reactions of carbohydrate-derived dienes and their carbocyclic analogs
  作者：Robert M. Giuliano、Alfonzo D. Jordan、A. Diane Gauthier、Karst Hoogsteen

  DOI：10.1021/jo00070a039

  日期：1993.8

  The Diels-Alder reactions of two dienes derived from carbohydrates and their carbocyclic analogs are described. The dienes (2S)-3,4-dihydro-2-methoxy-6-vinyl-2H-pyran (1) and (4R)-3,4-dihydro-4-methoxy-6-vinyl-2H-pyran(2) were synthesized from tri-O-acetyl-D-glucal. Cycloaddition reactions of these dienes, each of which contains a single methoxy group at either the allylic or anomeric position, were carried out with a series of dienophiles including N-phenylmaleimide, dimethyl acetylenedicarboxylate, diethyl azodicarboxylate, and N-phenyl-1,2,4-triazoline-3,5-dione. The incorporation of an amine base in the Diels-Alder reactions was found to be essential for the formation of good yields of unrearranged cycloadducts. Structures of the cycloadducts were assigned using NMR methods and X-ray crystallographic analysis. The diastereofacial selectivities observed for dienes 1 and 2 are compared with those of the analogous carbocyclic dienes 3 and 4, the former of which was synthesized for this study from m-anisic acid. Cycloadditions to both the carbohydrate-derived dienes and their carbocyclic analogs were found to occur with a preference for addition of the dienophile to the face of the diene opposite the methoxyl group in every case. The degree of stereoselectivity was sensitive to a number of factors including the location of the substituents attached to the ring of the semicyclic diene, the presence of oxygen in the ring, and the type of dienophile. The dominant trend for anti addition in the Diels-Alder reactions is discussed in terms of diene conformation and secondary orbital effects in the transition state for cycloaddition.
• Facile Synthesis of a Simplified Bicyclo[7.3.1] Esperamicin-Calicheamicin Enediyne Core
  作者：John F. Kadow、Donald J. Cook、Terrence W. Doyle、David R. Langley、Kahnie M. Pham、Dolatrai M. Vyas、Mark D. Wittman

  DOI：10.1016/s0040-4020(01)80632-3

  日期：1994.1

  An efficient non cobalt mediated route for the synthesis of a simplified bicycle [7.3.1]enediyne core of the naturally occurring calicheamicins and esperamicins is described. The key cyclization provides a single propargylic alcohol stereoisomer which is in the same relative configuration as that found in the naturally occurring calicheamicins and esperamicins. Selective functionalizations of the cyclized core via selenium dioxide oxidations are described. Installation of an enone chemical trigger provides a hydroxylated analog of a previously described biologically active synthetic enediyne.
• WEBSTER, FRANCIS X.;SILVERSTEIN, ROBERT M., SYNTHESIS,(1987) N 10, 922-924
  作者：WEBSTER, FRANCIS X.、SILVERSTEIN, ROBERT M.

  DOI：——

  日期：——