(S)-1-(4-Methoxy-benzenesulfonyl)-pyrrolidine-2-carbonyl chloride | 88867-98-5

• 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: (S)-1-(4-Methoxy-benzenesulfonyl)-pyrrolidine-2-carbonyl chloride
• 英文别名: (2S)-1-(4-methoxyphenyl)sulfonylpyrrolidine-2-carbonyl chloride
• CAS: 88867-98-5
• 化学式: C₁₂H₁₄ClNO₄S
• 分子量: 303.766
• InChiKey: VFOFMOGCWLUWLG-NSHDSACASA-N

物化性质

• 沸点：
  438.3±55.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-Methoxy-benzenesulfonyl)-pyrrolidine-2-carbonyl chloride 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-Allyl-9-[(S)-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carbonyl]-1,9-dihydro-β-carboline-2-carboxylic acid phenyl ester
  参考文献：
  名称：

  A Novel Synthesis of Chiral 1-Allyl-1,2,3,4-tetrahydro-β-carboline Employing Allyltributyltin and Chiral Acyl Chlorides

  摘要：

  β-咔啉在其9-位被手性酰氯酰化，然后与烯丙基三丁基锡和2,2,2-三氯乙基氯甲酸酯反应以非对映选择性方式提供1-烯丙基-1,2-二氢咔啉衍生物。 N-9位上的手性酰基很容易被碱水溶液消除，定量地得到羧酸，而C-1位上没有外消旋化。形成的1-烯丙基-1,2-二氢-β-咔啉转化为1-烯丙基-1,2,3,4-四氢-β-咔啉。

  DOI：

  10.1055/s-1999-2952
• 作为产物：
  描述：

  1-(4-Methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 48.0h， 生成 (S)-1-(4-Methoxy-benzenesulfonyl)-pyrrolidine-2-carbonyl chloride
  参考文献：
  名称：

  Synthesis and liquid chromatographic evaluation of some chiral derivatizing agents for resolution of amine enantiomers

  摘要：

  DOI：

  10.1021/ac00270a022

文献信息

• Short Synthesis of a Proline Amide Orexin Receptor Antagonist on the Pilot Plant Scale
  作者：Simone Tortoioli、Daniel Marchal、Martin Kesselgruber、Thomas Pabst、Wolfgang Skranc、Stefan Abele

  DOI：10.1021/op500277s

  日期：2014.12.19

  A three-step fully telescoped synthesis of an N-sulfonyl proline amide, a nonpeptide antagonist of human orexin receptors, is described. The process development from the medicinal chemistry route up to the 240 kg production of 1 is discussed with a focus on an economical and efficient amide bond formation and identification of a new polymorph. The routes are compared using green metrics.

  描述了三步全望远镜合成N-磺酰基脯氨酸酰胺（一种人类orexin受体的非肽拮抗剂）的方法。讨论了从药物化学路线到生产240公斤1的过程，重点是经济有效地形成酰胺键并鉴定出新的多晶型物。使用绿色指标比较路线。
• Preparation of both enantiomers of 1-allyl-1,2,3,4-tetrahydro-β-carboline using allyltin reagents and a chiral auxiliary derived from l-proline
  作者：Takashi Itoh、Yûji Matsuya、Yasuko Enomoto、Akio Ohsawa

  DOI：10.1016/s0040-4020(01)00684-6

  日期：2001.8

  beta -Carboline, which had an acyl group derived from L-proline at the 9-position, reacted with allyltributyltin and 2,2,2-trichloroethyl chloroformate, to afford an 1-allyl-1,2-dihydro-beta -carboline derivative in a diastereo selective manner. The chiral acyl group at N-9 was readily eliminated by aqueous alkali to give a corresponding carboxylic acid. The formed 1-allyl-1,2-dihydro-beta -carboline was transformed via two reduction steps to 1-alkyl-1,2,3,4-tetrahydro-beta -carboline in high ee. When the allylation was carried out using tetraallyltin instead of allyltributyltin, the stereoselectivity was reversed, and the antipode of the allyl adduct was obtained in high yield and ee in the presence of tin(IV) tetraiodide. Thus, it was found that both enantiomers of 1-allyl-beta -carboline were obtained in good enantioselectivities by the use of the same chiral auxiliary. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A Novel Synthesis of Chiral 1-Allyl-1,2,3,4-tetrahydro-β-carboline Employing Allyltributyltin and Chiral Acyl Chlorides
  作者：Takashi Itoh、Yûji Matsuya、Yasuko Enomoto、Kazuhiro Nagata、Michiko Miyazaki、Akio Ohsawa

  DOI：10.1055/s-1999-2952

  日期：1999.11

  β-Carboline was acylated at its 9-position by a chiral acyl chloride, followed by reaction with allyltributyltin and 2,2,2-trichloroethyl chloroformate to afford an 1-allyl-1,2-dihydrocarboline derivative in a diasteroselective manner. The chiral acyl group at N-9 was readily eliminated by aqueous alkali to give carboxylic acid quantitatively without racemization on C-1 position. The formed 1-allyl-1,2-dihydro-β-carboline was transformed to 1-allyl-1,2,3,4-tetrahydro-β-carboline.

  β-咔啉在其9-位被手性酰氯酰化，然后与烯丙基三丁基锡和2,2,2-三氯乙基氯甲酸酯反应以非对映选择性方式提供1-烯丙基-1,2-二氢咔啉衍生物。 N-9位上的手性酰基很容易被碱水溶液消除，定量地得到羧酸，而C-1位上没有外消旋化。形成的1-烯丙基-1,2-二氢-β-咔啉转化为1-烯丙基-1,2,3,4-四氢-β-咔啉。
• Synthesis and liquid chromatographic evaluation of some chiral derivatizing agents for resolution of amine enantiomers
  作者：C. Randall. Clark、Jeffrey M. Barksdale

  DOI：10.1021/ac00270a022

  日期：1984.5.1