adamantanesulfinyl chloride | 21280-43-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: adamantanesulfinyl chloride
• 英文别名: 1-adamantanesulphinyl chloride；Adamantane-1-sulfinyl Chloride
• CAS: 21280-43-3
• 化学式: C₁₀H₁₅ClOS
• 分子量: 218.748
• InChiKey: BHZSRFGORFYGLW-UHFFFAOYSA-N

物化性质

• 熔点：
  42-44 °C
• 沸点：
  336.4±25.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  adamantanesulfinyl chloride 在 potassium permanganate 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 2.25h， 生成 (S)-1-[(S)-2-(Adamantane-1-sulfonylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid (3,3,3-trifluoro-2-hydroxy-1-isopropyl-propyl)-amide
  参考文献：
  名称：

  Discovery and Biological Activity of Orally Active Peptidyl Trifluoromethyl Ketone Inhibitors of Human Neutrophil Elastase

  摘要：

  Previously we had shown that tripeptidyl trifluoromethyl ketones (TFMKs) possessing an N-terminal diarylacylsulfonamide, such as ICI 200,880 and ICI 200,355, displayed unparalleled protectin against the lung damage induced by human neutrophil elastase (HNE) when the inhibitors were administered intratracheally. Since the diarylacylsulfonamides were designed specifically to afford a long residence time in the lung, it was not unexpected that inhibitors from this class of TFMKs were not active when administered orally. Upon evaluating a large number of peptidyl TFMKs possessing a variety of N-terminal groups, several compounds were identified which demonstrated oral activity. Compounds were evaluated for their oral activity by measuring their ability to inhibit the increase in lung weight relative to body weight (Lw/Bw), the increase in red blood cells, and the increase in white blood cells induced by intratracheally administered HNE (100 mu g/hamster). A number of tripeptidyl trifluoromethyl ketones containing neutral N-terminal groups displayed good oral activity, while those containing basic, acidic, or polar groups did not. Compound 50, possessing an N-terminal 4-(CH3O)C6H4CO group, was particularly effective, reducing Lw/Bw by 77%, red cells by 89%, and white cells by 91% when dosed at 37.5 mg/kg orally. Thus, by modifying the N-terminal group of tripeptidyl TFMKs, inhibitors can be designed which are effective in vivo when administered either orally or intratracheally.

  DOI：

  10.1021/jm960819g
• 作为产物：
  描述：

  1-adamantyl-hydroxy-sulfanylidene-λ4-sulfane;N,N-diethylethanamine 在 氯化亚砜 作用下， 生成 adamantanesulfinyl chloride
  参考文献：
  名称：

  Mikolajczyk, Marian; Lyzwa, Piotr; Drabowicz, Jozef, Angewandte Chemie, 1989, vol. 101, # 1, p. 87 - 88

  摘要：

  DOI：

文献信息

• Peptide derivatives
  申请人：ICI Americas Inc.

  公开号：US04910190A1

  公开（公告）日：1990-03-20

  The invention concerns pharmaceutically useful trifluoromethyl ketone substituted di-, tri- and tetra-peptide derivatives of the formulae Ia, Ib, Ic set out hereinafter, and salts thereof, which are inhibitors of human leukocyte elastase. Also described herein are pharmaceutical compositions containing a peptide derivative and processes and intermediates for use in the manufacture of the peptide derivatives.

  本发明涉及具有药用价值的、三氟甲基酮取代的二肽、三肽和四肽衍生物，其结构式为Ia、Ib、Ic，以及它们的盐，这些衍生物是人类白细胞弹性蛋白酶的抑制剂。本文还描述了含有肽衍生物的药物组合物，以及用于制造这些肽衍生物的过程和中间体。
• Diastereomeric sulfinates derived from (l)-N-methylephedrine: synthesis, applications and rearrangements
  作者：Józef Drabowicz、Bogdan Bujnicki、Paolo Biscarini、Marian Mikołajczyk

  DOI：10.1016/s0957-4166(99)00336-5

  日期：1999.8

  The reaction of sulfinyl chlorides with (l)-N-methylephedrine alone or in the presence of tertiary amines was found to produce diastereomeric sulfinates with diastereomeric purities up to 90%. The diastereomeric ratio is strongly influenced by the nature of substituents on the sulfinyl chlorides and to some extent by the reaction conditions. In a few cases, the pure diastereomers were isolated by chromatography

  发现亚磺酰氯与（1）-N-甲基麻黄碱单独或在叔胺存在下的反应产生具有高达90％的非对映体纯度的非对映体亚磺酸盐。非对映体比率受亚磺酰氯上取代基的性质的强烈影响，并且在一定程度上受反应条件的影响。在少数情况下，通过色谱法分离纯的非对映异构体，并用于制备旋光性亚砜。还讨论了硅胶催化的亚磺酸盐重排为相应的砜。
• Acid-Catalyzed Hydrolysis of Some <i>N</i>,<i>N</i>-Dibenzylalkanesulfinamides in 50% Acetonitrile–Water
  作者：Mrityunjoy Datta、Alan J. Buglass

  DOI：10.1080/10426507.2012.704105

  日期：2013.6.1

  bimolecular neutral, acid-catalyzed, and acid-dependent nucleophilic (halide ion) catalysis pathways. The last-named is predominant in reactions in HBr solutions, but in HCl solutions, the acid-catalyzed pathway is predominant. The results indicate that both steric and electronic effects are important in these reactions. There appears to be no mechanistic switchover in the series 1→4. GRAPHICAL ABSTRACT

  摘要 研究了一些 N,N-二苄基链烷亚磺酰胺 (RSONH(CH2Ph)2; 1, R = Me; 2, R = iPr; 3, R = tBu; 4, R = 1-金刚烷基) 50% ( v:v) 氢溴酸和盐酸的乙腈-水溶液，主要在 44.8 °C，使用紫外 (UV) 分光光度法确定伪一级速率常数。发现这些化合物通过同时发生的双分子中性、酸催化和酸依赖性亲核（卤离子）催化途径水解。后一种反应在 HBr 溶液中占主导地位，但在 HCl 溶液中，酸催化途径占主导地位。结果表明空间和电子效应在这些反应中都很重要。在系列 1→4 中似乎没有机械转换。图形概要
• Pyrrolidine compounds and medicinal utilization thereof
  申请人：Mitsubishi Pharma Corporation

  公开号：US06468998B1

  公开（公告）日：2002-10-22

  The present invention provides a pyrrolidine compound of the formula (I) wherein each symbol is as defined in the specification, an optically active compound thereof and a pharmaceutically acceptable salt thereof. The present invention further provides a pharmaceutical composition containing a compound of the formula (I), an optically active compound thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive. The compound of the present invention has a serotonin 2 receptor antagonistic action along with a platelet aggregation suppressive action, a peripheral circulation improving action and a lacrimation promoting action. Therefore, the compound of the present invention can be a useful medicine showing effect against thrombotic embolism, dry eye and the like.

  本发明提供了一种式(I)的吡咯烷化合物，其中每个符号如规范中定义，以及其光学活性化合物和药学上可接受的盐。本发明还提供了一种含有式(I)的化合物、其光学活性化合物或药学上可接受的盐以及药学上可接受的添加剂的药物组合物。本发明的化合物具有血清素2受体拮抗作用，同时具有抑制血小板聚集、改善外周循环和促进泪液分泌的作用。因此，本发明的化合物可以是一种有益的药物，对抗血栓栓塞、干眼症等具有一定效果。
• Hydrolysis of <i>N-</i>Phenylalkanesulfinamides in Aqueous Mineral Acids
  作者：Mrityunjoy Datta、Alan J. Buglass、John G. Tillett

  DOI：10.1080/10426507.2010.508691

  日期：2011.2.28

  acid-catalyzed hydrolysis of N-phenylalkanesulfinamides (RSONHPh; 1, R = iPr; 2, R = tBu; 3, R = 1-adamantyl) has been studied in aqueous mineral acids. Hydrolysis was found to proceed via a slow spontaneous (uncatalyzed) pathway, an A-2 (bimolecular) acid-catalysis pathway, and an acid-dependent nucleophilic catalysis pathway, the last of which predominates in hydrobromic and hydrochloric acid solutions

  摘要 在含水无机酸中研究了 N-苯基链烷亚磺酰胺 (RSONHPh; 1, R = iPr; 2, R = tBu; 3, R = 1-金刚烷基) 的酸催化水解。发现水解通过缓慢的自发（未催化）途径、A-2（双分子）酸催化途径和酸依赖性亲核催化途径进行，最后一种在氢溴酸和盐酸溶液中占主导地位。在浓硫酸中检测到化合物 2 和 3 从 A-2 到 A-1 的机械转换。催化活性的顺序、添加盐的影响、Arrhenius 参数、动力学溶剂同位素和溶剂效应都与所提出的机制一致。图形概要