1-(chloromethyl)-5(R)-methyl-2-pyrrolidinone | 154747-82-7

• 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: 1-(chloromethyl)-5(R)-methyl-2-pyrrolidinone
• 英文别名: 5(R)-methyl-1-(chloromethyl)-2-pyrrolidinone；(5R)-5-methyl-1-(chloromethyl)-2-pyrrolidinone；(5R)-1-(chloromethyl)-5-methylpyrrolidin-2-one
• CAS: 154747-82-7
• 化学式: C₆H₁₀ClNO
• 分子量: 147.605
• InChiKey: YXSPRXDRLVSOEZ-RXMQYKEDSA-N

物化性质

• 沸点：
  248.3±23.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  仲丁胺 、 1-(chloromethyl)-5(R)-methyl-2-pyrrolidinone 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到
  参考文献：
  名称：

  5R-甲基-1-氯甲基-2-吡咯烷酮：确定手性非外消旋胺中的对映体过量1

  摘要：

  摘要 5R-甲基-1-氯甲基-2-吡咯烷酮与手性外消旋胺反应形成非对映加合物。质子 NMR 光谱中 N-CH2-O 信号的分析可以确定原始胺的对映体过量。

  DOI：

  10.1080/00397919808006868
• 作为产物：
  描述：

  (S)-(+)-5-羟甲基-2-吡咯烷酮对甲苯磺酸酯 在 三甲基氯硅烷 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium iodide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 14.0h， 生成 1-(chloromethyl)-5(R)-methyl-2-pyrrolidinone
  参考文献：
  名称：

  An optimised synthetic approach to a chiral derivatising agent and the utilisation of a dimerisation reaction in the synthesis of a novel C2-symmetric diphosphine ligand

  摘要：

  We report an optimised synthetic approach to the chiral derivatising agent (5R)-methyl-1-(chloromethyl)-2-pyrrolidinone. In addition, the observation of an unwanted dimerisation product is turned to our advantage by providing a method for the synthesis of a new class of C2-symmetric chiral diphosphine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.02.014

文献信息

• 5(R)-Methyl-1-(chloromethyl)-2-pyrrolidinone: a new reagent for the determination of enantiomeric composition of alcohols
  作者：Michael B. Smith、Bruce T. Dembofsky、Young Chan Son

  DOI：10.1021/jo00086a021

  日期：1994.4

  We have prepared a new chiral nonracemic reagent (5(R)-methyl-1-(chloromethyl)-2-pyrrolidinone) in enantiopure form that reacts with alcohols containing a stereogenic center to produce diastereomeric N-(alkoxymethyl)-2-pyrrolidinone derivatives. These derivatives exhibit large and easily observed diastereotopic signals in the proton NMR that allow direct determination of diastereomeric ratio (% dr) for the product.
• A One-Pot Process for the Enantioselective Synthesis of Amines via Reductive Amination under Transfer Hydrogenation Conditions
  作者：Glynn D. Williams、Richard A. Pike、Charles E. Wade、Martin Wills

  DOI：10.1021/ol035746r

  日期：2003.10.1

  Cyclic amines may be prepared via a sequence of deprotection followed by intramolecular reductive amination of t-Boc-protected amino ketones under asymmetric transfer hydrogenation conditions. In cases where the corresponding imine reaction proceeds with high enantioselectivity, this is reflected in the one-step process.
• Synthesis of N-aminomethylpyrrolidin-2-ones
  作者：Ping Chen、Dong-Jin Suh、Michael B. Smith

  DOI：10.1039/p19950001317

  日期：——

  Pyrrolidin-2-ones react with formaldehyde and chlorotrimethylsilane to give 1-chloromethylpyrrolidin-2-ones which upon subsequent reaction with primary and secondary amines give 1-aminomethylpyrrolidin-2-ones in good yield.
• Conformational Analysis of l-(Alkoxymethyl)-5(<i>R</i>)-methyl-2-pyrrolidinone Derivatives. Determination of the Absolute Stereochemistry of Alcohols
  作者：Shamil K. Latypov、Ricardo Riguera、Michael B. Smith、Jana Polivkova

  DOI：10.1021/jo980029+

  日期：1998.11.1

  Parameters that allow prediction of the sense of NMR nonequivalence in N-(alkoxymethyl)-2-pyrrolidinone derivatives (2-8) are identified. These derivatives are prepared by the reaction of chiral racemic and chiral nonracemic alcohols with 1-(chloromethyl)-5(R)-methyl-2-pyrrolidinone, 1. The factors governing NMR nonequivalence (Delta delta) in 2-8 were first established. The NMR parameters were then determined and compared with those derived from calculated conformations for 2-8. This information was used to establish the absolute stereochemistry of the alcohol adducts.
• 5R-Methyl-1-chloromethyl-2-pyrrolidinone: Determining Enantiomeric Excess in Chiral Nonracemic Amines¹
  作者：Ping Chen、Sheiwei Tao、Michael B. Smith

  DOI：10.1080/00397919808006868

  日期：1998.5

  Abstract 5R-Methyl-1-chloromethyl-2-pyrrolidinone reacts with chiral, racemic amines to form a diastereomeric adduct. Analysis of the N-CH2-O signals in the proton NMR spectra allows determination of the enantiomeric excess of the original amine.

  摘要 5R-甲基-1-氯甲基-2-吡咯烷酮与手性外消旋胺反应形成非对映加合物。质子 NMR 光谱中 N-CH2-O 信号的分析可以确定原始胺的对映体过量。