6-carbamoylcyclohex-3-enecarboxylic acid | 1469-49-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-carbamoylcyclohex-3-enecarboxylic acid
• 英文别名: (+/-)-cis-6-carbamoyl-cyclohex-3-enecarboxylic acid；(+/-)-cis-6-Carbamoyl-cyclohex-3-encarbonsaeure；rac-(1R,6S)-6-carbamoylcyclohex-3-ene-1-carboxylic acid, cis；(1S,6R)-6-carbamoylcyclohex-3-ene-1-carboxylic acid
• CAS: 1469-49-4；2028-12-8
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: AZDKWAUSBOZMHG-RITPCOANSA-N

物化性质

• 熔点：
  145-146 °C
• 沸点：
  438.2±45.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-carbamoylcyclohex-3-enecarboxylic acid 在 Rhodococcus rhodochrous IFO 15564 、 水 作用下， 以18%的产率得到cis-1,2,3,6-tetrahydrophthalic acid
  参考文献：
  名称：

  杜鹃红球菌IFO 15564介导的脂环式腈和酰胺的水解：立体选择性及其用于动力学拆分和不对称化的用途

  摘要：

  研究了由红球红球菌IFO 15564介导的脂环族单，二腈和酰胺水解的立体过程和选择性。底物的立体化学以及取代基的性质和脂环族环中双键的存在极大地影响了腈水合酶和酰胺酶的水解速度。在某些情况下，对映异构体或对映异构基团之间的速率差异使动力学拆分或不对称化成为可能。在5-苯甲酰氧基-3-环己烯-1-羧酰胺的水解中观察到酰胺酶的最高对映选择性（E＞ 200），因此5-羟基-3-环己烯-1-羧酸甲酯的两种对映异构体变得容易获得。

  DOI：

  10.1016/s0957-4166(98)00084-6
• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 ammonium hydroxide 作用下， 反应 0.5h， 生成 6-carbamoylcyclohex-3-enecarboxylic acid
  参考文献：
  名称：

  立体化学研究83饱和杂环76：部分饱和3,1-苯并恶嗪，3,1-苯并恶嗪-2-酮和3,1-苯并恶嗪-2-硫酮的制备和构象研究

  摘要：

  顺式和反式-2-氨基-4-环己烯-1-羧酸1和3与酰亚胺反应，生成稠合骨架的双环顺式和反式嘧啶-4-酮8和9。氨基酸1将3和3还原为顺式和反式1，3-氨基醇6和7，其通过酰亚胺化成双环四氢-4H-3，1-苯并恶嗪10和11，或通过相应的方法被转化。氨基甲酸酯14和15变成四氢4H-3,1-苯并恶嗪-2（1H）-一16和17。2-硫代类似物18和19是通过将氨基醇6和7经处理得到的二硫代氨基甲酸酯环化而制得的与二硫化碳。反式氨基醇7及其饱和类似物与对氯苯甲醛反应，分别得到六氢13和八氢-4H-3，1-苯并恶嗪13a。1 H和13 C NMR研究表明，与早期研究的类似的在位置1处含有氧或未取代氮的类似物一样，合成的顺式同构异构体8、10、16和18以优选的构象异构体的形式出现在N-inside型杂环扭曲反型中。 （准轴C 6 -N键）（B）。在含有饱和C-2原子的反式异构体（13和13a）中，H-2和H-6处于顺式相对位置。

  DOI：

  10.1016/s0040-4020(01)96537-8

文献信息

• Experimental studies of the anomeric effect
  作者：Harold Booth、Khedhair A. Khedhair、Hatif A.R.Y. Al-Shirayda

  DOI：10.1016/s0040-4020(01)85926-3

  日期：1988.1

  The positions of conformational equilibria due to the double ring inversion in cis-decahydroquinazoline (7 ⇄ 8) and cis-decahydro-3-methylquinazoline (9 ⇄ 10) were determined by 13C n.m.r. spectroscopy in the range 215-225 K. In both cases there is a very strong preference (-ΔG7→8o 1.08 kcal mol-1; -ΔG9→10o 1.10 kcal mol-1) for the conformation which would allow the lone pairs on N(1) and N(3) to lie

  通过13 C nmr光谱在215-225 K范围内测定了顺式十氢喹唑啉（778 ）和顺式十氢-3-甲基喹唑啉（9910）中双环倒置引起的构象平衡位置。的情况下，构象有一个非常强烈的偏好（-ΔG7 →8 o 1.08 kcal mol -1；-ΔG9 →10 o 1.10 kcal mol -1），这将允许在N（1）和N（3 ）躺在分子受阻的“内部”面上。但是，值3顺式十氢-3-甲基喹唑啉（10）和顺式（4aH，8aH）顺式（2H，8aH）-十氢-2,3-二甲基喹唑啉（14）的J（CHNH）耦合常数表明N在N（1）更喜欢N（1）-H位于“内侧”（轴向）且N（1）-孤对赤道的构象，因此证明了端基异构化作用胜过空间排斥的能力。
• Preparation and steric structure of partially saturated isoindolo[1,3]- and -[3,1]benzoxazinones and -[2,4]benzoxazepinones
  作者：Pál Sohár、Géza Stájer、Katalin Nagy、Gábor Bernáth

  DOI：10.1002/mrc.1260330503

  日期：1995.5

  From cis‐2‐(p‐methylbenzoyl)cyclohexanecarboxylic acid (1), diendo‐3‐(p‐methylbenzoyl)bicyclo[2.2.1]heptane‐2‐carboxylic acid (2) or 2‐(p‐methylbenzoyl)benzoic acid (3) with stereoisomeric 1,3‐ or 1,4‐amino alcohols with cyclohexane/ene or norbornane/ene skeletons, various partially or fully saturated isoindolo[1,2‐b] [1,3]‐ and ‐[2,1‐a] [3,1]benzoxazinones methylene‐bridged derivatives and [1,2‐c]

  来自顺式-2-(对甲基苯甲酰基)环己烷甲酸 (1)、二烯基-3-(对甲基苯甲酰基)双环[2.2.1]庚烷-2-甲酸(2)或2-(对甲基苯甲酰基)苯甲酸(3) 具有环己烷/烯或降冰片烷/烯骨架的立体异构体1,3-或1,4-氨基醇，各种部分或完全饱和的异吲哚并[1,2-b][1,3]-和-[2，制备了 1-a] [3,1] 苯并恶嗪酮亚甲基桥联衍生物和 [1,2-c] [2,4] 苯并恶嗪酮。对于这些含有两个杂环和两个或三个环烷烃环的化合物，通过 1H 和 13C NMR 光谱（包括 DNOE、DEPT 和 2D-​​HSC 测量）建立了立体结构（末端环和芳基的退火）。
• Modification of the Enantioselectivity of Biocatalytic <i>meso</i> ‐Desymmetrization for Synthesis of Both Enantiomers of <i>cis</i> ‐1,2‐Disubstituted Cyclohexane by Amidase Engineering
  作者：Hui‐Juan Hu、Qi‐Qiang Wang、De‐Xian Wang、Yu‐Fei Ao

  DOI：10.1002/adsc.202100597

  日期：2021.10.5

  Both enantiomers of cis-1,2-disubstituted cyclohexane have been obtained enantioselectively through engineered amidase-catalyzed desymmetrization of meso carbocyclic 1,2-dicarboxamides under mild condition. Based on the enzyme-substrate binding model suggested by molecular docking, the amplification and reversal of enantioselectivity of amidase was quickly achieved through generating and testing only

  通过工程酰胺酶催化的内消旋碳环 1,2-二甲酰胺在温和条件下的去对称化，对映选择性地获得了顺式-1,2-二取代环己烷的两种对映异构体。基于分子对接提出的酶-底物结合模型，仅产生和测试8个变体，就迅速实现了酰胺酶对映选择性的放大和逆转。MD 模拟揭示了酰胺酶对映偏爱的起源，并揭示了对酰胺酶变体的对映选择性逆转的原因。通过将产物直接转化为对映异构纯杂环化合物，证明了生物催化介观去对称化的合成应用。
• MODIFIED BLOCK COPOLYMER COMPOSITION
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0085115A1

  公开（公告）日：1983-08-10

  A resinous modified block copolymer composition having excellent impact resistance, adhesiveness, coating properties, weatherability, heat deterioration resistance, transparency, and luster and rubbery and leather-like modified block copolymer compositions having excellent heat resistance, abrasion resistance, press distortion resistance, adhe- i siveness, transparency, oil resistance, weatherability, and heat deterioration resistance, which comprises a thermoplastic polymer and a modified block copolymer in which a molecular unit having a carboxylic acid group and/or a derivative group thereof is bound to a fundamental block copolymer composed of a monovinyl-substituted aromatic hydrocarbon polymer block and an olefin compound polymer block having an unsaturation degree of 20% or less.

  一种树脂改性嵌段共聚物组合物，具有优异的抗冲击性、粘附性、涂覆性、耐候性、耐热劣化性、透明度和光泽，以及橡胶和皮革状改性嵌段共聚物组合物，具有优异的耐热性、耐磨性、耐压变形性、粘附性、透明度、耐油性、耐候性和耐热劣化性、热塑性聚合物和改性嵌段共聚物，其中具有羧酸基团和/或其衍生物基团的分子单 位与基本嵌段共聚物结合，基本嵌段共聚物由单乙烯基取代的芳香烃聚合物嵌段 和不饱和度为 20%或以下的烯烃化合物聚合物嵌段组成。
• 1,3-Diaryl-4,5,6,7-tetrahydro-2<i>H</i>-isoindole Derivatives:  A New Series of Potent and Selective COX-2 Inhibitors in Which a Sulfonyl Group Is Not a Structural Requisite
  作者：Bernard Portevin、Charles Tordjman、Philippe Pastoureau、Jacqueline Bonnet、Guillaume De Nanteuil

  DOI：10.1021/jm990965x

  日期：2000.11.1

  Novel tetrahydro-2H-isoindoles have been prepared and evaluated as inhibitors of the COX-2 isoenzyme. A 1,S-diaryl substitution on the central polycyclic ring system and absence of a sulfonyl moiety are the two structural features of this chemical series. A short and easy synthetic pathway produced several derivatives which were shown to be potent and selective COX-2 vs COX-1 inhibitors (IC50 = 0.6-100 nM for COX-2, 100->1000 nM for COX-1). Structural modifications established that a bicyclic ring appended to the pyrrole nucleus and 4,4'-difluoro substitution on the phenyl rings were optimal for high inhibitory potency. Activity was confirmed in the human whole blood assay and subsequently in the murine air-pouch model in which in vivo PGE2 inhibitory activity was evaluated with respect to gastric tolerance (ED50 for inhibition of exudate PGE2 of 3 mg/kg and gastric PGEB of 20 mg/kg). Gastric tolerance was further assessed after administration to mice of high doses (up to 400 mg/kg) of the inhibitors by measurement of gastric damage. This panel of studies allowed selection of a number of tetrahydro-2H-isoindoles which were compared in the adjuvant-induced arthritis model. Compounds 32 and 37 showed the most potent activity with ED50 values for edema inhibition in the noninjected paw of 0.35 and 0.15 mg/kg/day, respectively, after oral administration. In addition, this interesting antiinflammatory profile was accompanied by a protective effect against arthritis-induced osteopenia, the decrease being 50% with a dose of 0.25 mg/kg/day.