methyl (S)-1-[(1S)-1-phenylethyl]pyrrolidine-2-carboxylate | 256366-58-2

• 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: methyl (S)-1-[(1S)-1-phenylethyl]pyrrolidine-2-carboxylate
• 英文别名: N-[(S)-α-methylbenzyl]-(S)-proline methyl ester；N-[(S)-alpha-methylbenzyl]-(S)-proline methyl ester；methyl (2S)-1-[(1S)-1-phenylethyl]pyrrolidine-2-carboxylate
• CAS: 256366-58-2
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: RAKGXTSCJYFBIW-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (S)-1-[(1S)-1-phenylethyl]pyrrolidine-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以85%的产率得到{(2S)-1-[(S)-1-phenylethyl]pyrrolidin-2-yl}methanol
  参考文献：
  名称：

  Enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines catalyzed by β-aminoalcohols with the prolinol skeleton

  摘要：

  Several beta-aminoalcohols with the prolinol framework are shown to be very efficient catalysts for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines. The use of 0.5 equiv of the catalyst leads to the expected addition products in good yields and with ee up to 94% in a reaction time of only 4 It at room temperature. This ee is the highest value reported so far using 0.5 equiv of an aminoalcohol as a promoter. High enantioselectivities are obtained in the addition of dialkylzincs to both aromatic and aliphatic imines. The amount of the catalyst can be reduced to 0.25 equiv with a slight decrease in the ee. A very interesting effect of the addition rate and temperature on the enantioselectivity was also observed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.006
• 作为产物：
  描述：

  L-脯氨酸甲酯盐酸盐 、 (1-溴乙基)苯 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以20%的产率得到methyl (S)-1-[(1S)-1-phenylethyl]pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines catalyzed by β-aminoalcohols with the prolinol skeleton

  摘要：

  Several beta-aminoalcohols with the prolinol framework are shown to be very efficient catalysts for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines. The use of 0.5 equiv of the catalyst leads to the expected addition products in good yields and with ee up to 94% in a reaction time of only 4 It at room temperature. This ee is the highest value reported so far using 0.5 equiv of an aminoalcohol as a promoter. High enantioselectivities are obtained in the addition of dialkylzincs to both aromatic and aliphatic imines. The amount of the catalyst can be reduced to 0.25 equiv with a slight decrease in the ee. A very interesting effect of the addition rate and temperature on the enantioselectivity was also observed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.006

文献信息

• Optically active cyclic amino acid ester derivatives and processes for producing the same
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP0976729A1

  公开（公告）日：2000-02-02

  There are disclosed a process for producing an optically active cyclic amino acid ester derivative of formula (I): wherein R1 represents a C1 - C8 alkyl group; R2 represents a hydrogen atom, a C1 - C8 alkyl group, a halogen atom, a hydroxy group or a C1 - C8 alkoxy group; R3 represents an aryl group or a C1 - C8 alkyl group, which alkyl group is unsubstituted or substituted by an aryl group; n represents an integer from 1 to 4; and a and b, which are the same or different, represent R or S, by an optical resolution method, and a process for producing an optically active cyclic amino acid using the compound of formula (I).

  本发明公开了一种生产式 (I) 的光学活性环氨基酸酯衍生物的工艺： 其中 R1 代表 C1 - C8 烷基； R2 代表氢原子、C1 - C8 烷基、卤素原子、羟基或 C1 - C8 烷氧基； R3 代表芳基或 C1 - C8 烷基，该烷基未被取代或被芳基取代； n 代表 1 至 4 的整数；以及 相同或不同的 a 和 b 代表 R 或 S、 通过光学解析法，以及使用式（I）化合物生产光学活性环状氨基酸的工艺。
• 光学活性環式アミノ酸エステル誘導体およびその製造方法
  申请人：住友化学工業株式会社

  公开号：JP2000044539A

  公开（公告）日：2000-02-15

  (57)【要約】\n【課題】 光学活性環式アミノ酸エステル誘導体を提供すること。\n【解決手段】 一般式（１）\n（式中、Ｒ1はＣ１〜Ｃ８のアルキル基を表し、Ｒ2は水素原子、Ｃ１〜Ｃ８のアルキル基、ハロゲン原子、水酸基、Ｃ１〜Ｃ８のアルコキシル基を表し、Ｒ3はアリール基またはアリール基で置換されていてもよいＣ１〜Ｃ８のアルキル基を表し、ｎは１〜４の整数を、ａ、ｂはそれぞれ不斉炭素原子を表す。 ）で表される光学活性環式アミノ酸エステル誘導体またはそのジアステレオマー混合物。

  (57) [摘要] Јn [问题] 提供光学活性环氨基酸酯衍生物。 \解决方案] 通式（1）Јn（其中 R1 代表 C1 至 C8 烷基，R2 代表氢原子、C1 至 C8 烷基、卤素原子、羟基或 C1 至 C8 烷氧基，R3 代表芳基或可被芳基取代的 C1 至 C8 烷基，n 为 a 和 b 各代表一个手性碳原子。 光学活性环氨基酸酯衍生物或其非对映混合物由 (a) 表示。
• US06172234B2
  申请人：——

  公开号：——

  公开（公告）日：——
• US6172234B1
  申请人：——

  公开号：US6172234B1

  公开（公告）日：2001-01-09
• Enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines catalyzed by β-aminoalcohols with the prolinol skeleton
  作者：Raquel Almansa、David Guijarro、Miguel Yus

  DOI：10.1016/j.tetasy.2007.11.006

  日期：2007.11

  Several beta-aminoalcohols with the prolinol framework are shown to be very efficient catalysts for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines. The use of 0.5 equiv of the catalyst leads to the expected addition products in good yields and with ee up to 94% in a reaction time of only 4 It at room temperature. This ee is the highest value reported so far using 0.5 equiv of an aminoalcohol as a promoter. High enantioselectivities are obtained in the addition of dialkylzincs to both aromatic and aliphatic imines. The amount of the catalyst can be reduced to 0.25 equiv with a slight decrease in the ee. A very interesting effect of the addition rate and temperature on the enantioselectivity was also observed. (c) 2007 Elsevier Ltd. All rights reserved.