(S)-N-苯甲酰甲酰基-2-(甲氧基甲基)吡咯烷 | 113742-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-N-苯甲酰甲酰基-2-(甲氧基甲基)吡咯烷
• 英文名称: (S)-N-benzoylformyl-2-(methoxymethyl)pyrrolidine
• 英文别名: 2(S)-methoxymethylpyrrolidine benzoylamide；1-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-2-phenylethane-1,2-dione
• CAS: 113742-94-2
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: OBOMMYWNZMCTBI-LBPRGKRZSA-N

物化性质

• 沸点：
  361.4±34.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-苯甲酰甲酰基-2-(甲氧基甲基)吡咯烷 在 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以92%的产率得到(S)-2-Hydroxy-1-((S)-2-methoxymethyl-pyrrolidin-1-yl)-2-phenyl-ethanone
  参考文献：
  名称：

  Diastereoselective reduction and carboncarbon bond formation of α-keto esters/amides with SmI2

  摘要：

  The stereoselective reduction of alpha -keto esters/alpha -keto amides, which have various chiral auxiliaries using SmI2, is examined. 2(S)-Methoxymethylpyrrolidine, 1,1,2(S)- and 1,1,2(R)-triphenylethanediol were found to be suitable chiral auxiliaries that produced the corresponding alpha -hydroxy ester and amide in good diastereoselectivity with satisfactory yields. Allylation, the Reformatsky-type reaction, and the ketyl-alkene coupling reaction with the 1,1,2(R)-triphenylethanediol and 2(S)-methoxymethylpyrrolidine, derivative of the alpha -keto ester/amide proceeded smoothly with high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00676-1
• 作为产物：
  描述：

  (S)-(+)-2-(甲氧基甲基)吡唑烷 、 苯甲酰甲酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以64%的产率得到(S)-N-苯甲酰甲酰基-2-(甲氧基甲基)吡咯烷
  参考文献：
  名称：

  有机金属化合物与手性α-酮酰胺的立体控制加成反应

  摘要：

  在几种有机金属化合物与手性苯甲酰甲酰胺（由苯甲酰甲酸和（S）-2-（甲氧基甲基）吡咯烷制备）的加成反应中，可以使用镁基和钛基试剂实现互补立体选择，从而得到不同的 atrolactamide 非对映异构体。另一方面，苯基金属化合物与相应的丙酮酰胺反应得到 (S)-atrolactamide。

  DOI：

  10.1246/bcsj.63.1894

文献信息

• Highly Diastereoselective Reduction of New Chiral α-Ketoamides
  作者：Il Suk Byun、Yong Hae Kim

  DOI：10.1080/00397919508015873

  日期：1995.7

  Both pyruvamide and benzoylformamide having (S)-2-methoxymethylindoline as a chiral auxiliary were reduced with various reducing agents in high stereoselectivities (up to dr = 99 : 1).
• Diastereoselective reduction and carboncarbon bond formation of α-keto esters/amides with SmI2
  作者：Shin-ichi Fukuzawa、Manabu Miura、Hiroshi Matsuzawa

  DOI：10.1016/s0040-4039(01)00676-1

  日期：2001.6

  The stereoselective reduction of alpha -keto esters/alpha -keto amides, which have various chiral auxiliaries using SmI2, is examined. 2(S)-Methoxymethylpyrrolidine, 1,1,2(S)- and 1,1,2(R)-triphenylethanediol were found to be suitable chiral auxiliaries that produced the corresponding alpha -hydroxy ester and amide in good diastereoselectivity with satisfactory yields. Allylation, the Reformatsky-type reaction, and the ketyl-alkene coupling reaction with the 1,1,2(R)-triphenylethanediol and 2(S)-methoxymethylpyrrolidine, derivative of the alpha -keto ester/amide proceeded smoothly with high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Stereocontrolled Addition Reaction of Organometallics to Chiral α-Keto Amides
  作者：Tamotsu Fujisawa、Yutaka Ukaji、Makoto Funabora、Mikio Yamashita、Toshio Sato

  DOI：10.1246/bcsj.63.1894

  日期：1990.7

  Complementary stereoselection in the addition reaction of several organometallics to chiral benzoylformamide, prepared from benzoylformic acid and (S)-2-(methoxymethyl)pyrrolidine, could be achieved using magnesium- and titanium-based reagents to give differeent diastereomers of atrolactamide. On the other hand, the reaction of phenyl metallics to the corresponding pyruvamide afforded (S)-atrolactamide

  在几种有机金属化合物与手性苯甲酰甲酰胺（由苯甲酰甲酸和（S）-2-（甲氧基甲基）吡咯烷制备）的加成反应中，可以使用镁基和钛基试剂实现互补立体选择，从而得到不同的 atrolactamide 非对映异构体。另一方面，苯基金属化合物与相应的丙酮酰胺反应得到 (S)-atrolactamide。