(S)-(-)-5-(Chloromethyl)-2-pyrrolidinone | 72479-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-(-)-5-(Chloromethyl)-2-pyrrolidinone
• 英文别名: (S)-(-)-5-(chloromethyl)-2-pyrrolidone；(-)-(5S)-5-(Chloromethyl)-2-pyrrolidinone；(S)-5-(Chloromethyl)pyrrolidin-2-one；(5S)-5-(chloromethyl)pyrrolidin-2-one
• CAS: 72479-04-0
• 化学式: C₅H₈ClNO
• 分子量: 133.578
• InChiKey: PEUZYLPIDORLKM-BYPYZUCNSA-N

物化性质

• 熔点：
  53-55 °C
• 沸点：
  106.5-107.0 °C(Press: 0.15 Torr)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-(-)-5-(Chloromethyl)-2-pyrrolidinone 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (S)-4,5-diamino valeric acid dihydrochloride
  参考文献：
  名称：

  Synthesis of (R)- and (S)-4,5-diaminovaleric acids

  摘要：

  DOI：

  10.1021/jo00033a044
• 作为产物：
  描述：

  L-焦谷氨酸乙酯 在 sodium tetrahydroborate 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (S)-(-)-5-(Chloromethyl)-2-pyrrolidinone
  参考文献：
  名称：

  Synthesis of (R)- and (S)-4,5-diaminovaleric acids

  摘要：

  DOI：

  10.1021/jo00033a044

文献信息

• Protected Chloroethyl and Chloropropyl Amines as Conformationally Unrestricted Annulating Reagents
  作者：Qing Shi、Mariah C. Meehan、Michael Galella、Hyunsoo Park、Purnima Khandelwal、John Hynes、T. G. Murali Dhar、David Marcoux

  DOI：10.1021/acs.orglett.7b03548

  日期：2018.1.19

  The purpose of this letter is to document the use of protected chloroethyl and chloropropyl amines as conformationally unrestricted ambiphilic reagents that undergo annulation reactions with Michael acceptors. This reaction is wide in scope and utilizes reagents that are commercially available, inexpensive, and stable. Furthermore, this reaction is easy to execute and proceeds rapidly.

  这封信的目的是证明使用受保护的氯乙基和氯丙基胺作为构象不受限制的双歧试剂，该试剂与迈克尔受体发生环化反应。该反应的范围很广，并且使用了可商购的，廉价的和稳定的试剂。此外，该反应易于进行并且迅速进行。
• Pyrrolidone compounds for treating cerebral disorders
  申请人：Adir et Compagnie

  公开号：US05066651A1

  公开（公告）日：1991-11-19

  New pyrrolidone compounds of the formula: ##STR1## in which: R is OR", SR" or N (R.sub.3 R.sub.4) R' is optionally substituted alkyl or aryl, and the carbon in the 5-position of the pyrrolidone ring, which is substituted by CH.sub.2 R has the R or S configuration. These new compounds and their physiologically tolerable salts may be used therapeutically especially in the treatment of asthenias, ischaemic syndromes and nervous disorders associated with normal or pathological ageing.

  公式为：##STR1##其中：R为OR"、SR"或N（R.sub.3 R.sub.4）；R'为可选择取代的烷基或芳基；以及吡咯烷酮环的5位碳原子由CH.sub.2取代，R为R或S构型。这些新化合物及其生理耐受盐可在治疗虚弱症、缺血综合征以及与正常或病理性衰老相关的神经紊乱中得到治疗。
• 一种药物中间体的合成方法
  申请人：江苏福瑞生物医药有限公司

  公开号：CN104926707B

  公开（公告）日：2017-10-27

  本发明涉及医药化学领域，特别是涉及药物合成领域，更为具体的说是涉及一种药物中间体的合成方法。本发明中以4‑溴代联苯为起始原料，通过与硼化物反应得到化合物Ⅱ，化合物Ⅱ的反应液经过处理或者不处理直接以反应后溶液为原料进一步合成目标化合物。采用本发明所公开的合成路线，生产工艺简单、产品收率高、纯化处理简单，简单处理后产品纯度高，制备成本低，适合于工业化生产。
• Syntheses of (S)-5-substituted 4-aminopentanoic acids: a new class of .gamma.-aminobutyric acid transaminase inactivators
  作者：Richard B. Silverman、Mark A. Levy

  DOI：10.1021/jo01293a011

  日期：1980.2
• Syntheses Via Vinyl Sulfones. 58. A Triply Convergent Total Synthesis of a Symchiral Pyrrolidine-Fused Prostacyclin Analog
  作者：D. C. Smith、P. L. Fuchs

  DOI：10.1021/jo00114a016

  日期：1995.5

  The synthesis of symchiral 1-azatricyclo[6.3.0.0(2,6)]undeca-5-enyl prostaglandin I-2 analog 34 is reported. Construction of the tricyclic skeleton of 34 was accomplished in two steps by employing a triply convergent approach which utilized vinyl sulfone technology. Introduction of the heterocyclic subunit of 34 was achieved by an S(N)2'-thio-Claisen rearrangement which efficiently coupled a thiolactam moiety to a suitable allylic vinyl sulfone. Annulation of bicyclic vinyl sulfones 20, 23, and 29 was accomplished via a conjugate addition of Lithium acetylide 11 to the vinyl sulfone moieties, followed by an intramolecular S(N)2 displacement of a suitable nucleofuge. Competition between intramolecular carbon alkylation and beta-elimination of stabilized nitrogen anions from intermediate a-sulfonyl anions 20-i, 23-i, 29-i was discussed. Refunctionalization of the resulting tricyclic skeleton was accomplished by employing standard literature protocols. Compound 34 was found to be essentially inactive as an inhibitor of collagen-induced platelet aggregation, having an IC50 of > 10 mu M.