(R)-(+)-2-Methoxymethyl-pyrrolidin-1-dithiocarbonsaeure-benzyl-ester | 177082-91-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-(+)-2-Methoxymethyl-pyrrolidin-1-dithiocarbonsaeure-benzyl-ester
• CAS: 177082-91-6
• 化学式: C₁₄H₁₉NOS₂
• 分子量: 281.443
• InChiKey: XBPPSXQQPDBHKL-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.47
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-Methoxymethyl-pyrrolidin-1-dithiocarbonsaeure-benzyl-ester 、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以35.9%的产率得到(R)-2-Methoxymethyl-pyrrolidin-1-dithiocarbonsaeure-(1-phenyl-ethyl)-ester
  参考文献：
  名称：

  Synthese und Reaktionen chiraler, von (R)-(?)-bzw. (S)-(+)-2-Methoxymethylpyrrolidin abgeleiteter Dithiocarbamate

  摘要：

  The synthesis, diastereoselective alkylation reactions, dithiocarboxylation, and aldol condensation of several substituted methyl (R(1)-CH2) (S)-2-(methoxymethyl)-pyrrolidine-1 -dithiocarboxylates (S)-2 and of the corresponding (R)-derivatives (R)-2 are described. The new enantiomeric dithiocarbamates (S)-2a-e, and (R)-2a-d are obtained by reaction of(S)-(+)- [(S)-1] or (R)-(-)-2-(methoxymethyl)-pyrrolidine [(R)-1], respectively, with carbon disulfide in dry methanol/anhydrous sodium acetate and the appropriate alkylating agent. The cyclic ketene dithioacetals (S)-3 and (R)-3 are formed by dithiocarboxylation procedure of (S)-2a and (R)-2a whereas (S)-6 and (R)-6 are obtained by aldol reaction with isobutyraldehyde. (S)-2c,d and (R)-2c,d react in a diastereoselective manner after deprotonation with n-BuLi or LiTMP/LiBr at -78 degrees C in THF with alkyl halides to the enantiomeric compounds 4a/ent-4a, 4b/ent-4b and 5/ent-5, respectively.

  DOI：

  10.1002/prac.19963380130
• 作为产物：
  描述：

  二硫化碳 、 溴甲苯 、 (R)-(-)-2-(甲氧基甲基)吡咯烷 在 sodium acetate 作用下， 以 甲醇 为溶剂， 以66.6%的产率得到(R)-(+)-2-Methoxymethyl-pyrrolidin-1-dithiocarbonsaeure-benzyl-ester
  参考文献：
  名称：

  Synthese und Reaktionen chiraler, von (R)-(?)-bzw. (S)-(+)-2-Methoxymethylpyrrolidin abgeleiteter Dithiocarbamate

  摘要：

  The synthesis, diastereoselective alkylation reactions, dithiocarboxylation, and aldol condensation of several substituted methyl (R(1)-CH2) (S)-2-(methoxymethyl)-pyrrolidine-1 -dithiocarboxylates (S)-2 and of the corresponding (R)-derivatives (R)-2 are described. The new enantiomeric dithiocarbamates (S)-2a-e, and (R)-2a-d are obtained by reaction of(S)-(+)- [(S)-1] or (R)-(-)-2-(methoxymethyl)-pyrrolidine [(R)-1], respectively, with carbon disulfide in dry methanol/anhydrous sodium acetate and the appropriate alkylating agent. The cyclic ketene dithioacetals (S)-3 and (R)-3 are formed by dithiocarboxylation procedure of (S)-2a and (R)-2a whereas (S)-6 and (R)-6 are obtained by aldol reaction with isobutyraldehyde. (S)-2c,d and (R)-2c,d react in a diastereoselective manner after deprotonation with n-BuLi or LiTMP/LiBr at -78 degrees C in THF with alkyl halides to the enantiomeric compounds 4a/ent-4a, 4b/ent-4b and 5/ent-5, respectively.

  DOI：

  10.1002/prac.19963380130