(2S-顺式)-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸钾 | 4027-63-8

• 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
• 中文名称: (2S-顺式)-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸钾
• 中文别名: 氢氧化N-乙基-3-羟基-N,N-二甲基苯胺基正离子
• 英文名称: Penicillanic acid potassium salt
• 英文别名: potassium salt of penicillanic acid；Potassium (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate；potassium;(2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 4027-63-8
• 化学式: C₈H₁₀NO₃S*K
• 分子量: 239.337
• InChiKey: YCVAUSPCVZIJLE-IBTYICNHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.81
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  85.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S-顺式)-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸钾 在 盐酸 作用下， 生成 (2R,4S)-2-Carboxymethyl-5,5-dimethyl-thiazolidine-4-carboxylic acid 、 (2S,4S)-2-Carboxymethyl-5,5-dimethyl-thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  .beta.-Secondary and Solvent Deuterium Kinetic Isotope Effects and the Mechanisms of Base- and Acid-Catalyzed Hydrolysis of Penicillanic Acid

  摘要：

  beta-Secondary and solvent deuterium kinetic isotope effects have been determined at 25 degrees C for the alkaline and acid-catalyzed hydrolysis of penicillanic acid. In order to determine the former isotope effect, [6,6-H-2(2)]dideuteriopenicillanic acid has been synthesized. In alkaline solution, the former isotope effect (corrected to the effect of a single hydrogen orthogonal to the plane of the carbonyl group and for the inductive effect of deuterium) was found to be 0.95 +/- 0.01 and the latter 0.76 +/- 0.01. These values support the B(AC)2 mechanism of hydrolysis with rate-determining formation of the tetrahedral intermediate that has been proposed for other beta-lactams. The measured beta-secondary kinetic isotope for the acid-catalyzed reaction was 1.00 +/- 0.01. This represents a value averaged from experiments in 0.45 M HCl, 0.97 NI HCl, 4.5 M HCl, and 33.3 wt % H2SO4. All precedent suggests that this result would be very unlikely for an associative mechanism, such as that commonly observed (A(AC)2) for amide hydrolysis at these acid concentrations. Semiempirical AM1 calculations suggest that bicyclic beta-lactams are not only very weakly basic (in accord with previous experiment) but also protonate preferentially on nitrogen. This likelihood, taken with the secondary isotope effect, indicates that a likely pathway of acid-catalyzed hydrolysis would be that of an A(AC)1 mechanism with an intermediate acylium ion. If this were so, the calculated beta-secondary isotope effect per hydrogen coplanar with the breaking C-N bond and corrected for the inductive effect of deuterium would be 1.06 +/- 0.01. This suggests an early A(AC)1 transition state, which would be reasonable in this case because of destabilization of the N-protonated amide with respect to the acylium ion because of ring strain. The absence of specific participation by solvent in the transition state, as would be expected of an A(AC)1 but not an associative mechanism, is supported by the strongly inverse solvent deuterium kinetic isotope effect of 0.25 +/- 0.00 in 1 M HCl and 0.22 +/- 0.01 in 33.3 wt % H2SO4.

  DOI：

  10.1021/jo00111a020
• 作为产物：
  描述：

  6,6-二溴青霉烷酸 生成 (2S-顺式)-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸钾
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Ester of 1,1-dioxopenicillanic acid, and use thereof as .beta.-lactamase
  申请人：Kanebo Ltd.

  公开号：US04448769A1

  公开（公告）日：1984-05-15

  A 1,1-dioxopenicillanic acid ester represented by formula (I) ##STR1## wherein R represents a methyl or phenyl group. The ester of formula (I) may be prepared by reacting 1,1-dioxopenicillanic acid or its salt with a compound represented by formula (III) ##STR2## wherein R is as defined above, and X represents a halogen atom, or by oxidizing a compound of formula (V) ##STR3## wherein R is as defined above. The ester of the formula (I) is useful as a .beta.-lactamase inhibitor and may be used in association with a .beta.-lactam antibiotic.

  由以下公式（I）表示的1,1-二氧代青霉烷酸酯 在公式（I）中，R代表甲基或苯基。公式（I）的酯可以通过将1,1-二氧代青霉烷酸或其盐与以下公式（III）代表的化合物反应而制备 在公式（III）中，R如上所定义，X代表卤素原子，或者通过氧化以下公式（V）的化合物而制备 在公式（V）中，R如上所定义。公式（I）的酯可用作β-内酰胺酶抑制剂，并可与β-内酰胺类抗生素一起使用。
• ——
  作者：IKEHDA SEDZI、 MORIYAMA KATSU、 TSUKAMOTO GORO、 XIRADZIMA TSUNEHSUKEH、 NISI+

  DOI：——

  日期：——