(S)-1-methyl-2-[(indolinyl)methyl]pyrrolidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-1-methyl-2-[(indolinyl)methyl]pyrrolidine
• 英文别名: 1-[[(2S)-1-methylpyrrolidin-2-yl]methyl]-2,3-dihydroindole
• 化学式: C₁₄H₂₀N₂
• 分子量: 216.326
• InChiKey: IQOPRGDYWWXBQK-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-羟基-3-甲基丁酸 、 (S)-1-methyl-2-[(indolinyl)methyl]pyrrolidine 以 氘代氯仿 为溶剂， 生成
  参考文献：
  名称：

  L-脯氨酸衍生物作为手性转移剂在羧酸对映体识别中的应用

  摘要：

  四脯氨酸衍生的手性受体5，6，7，8分别容易地合成从开始大号脯氨酸。手性受体的对映体识别能力用一系列羧酸按11 H NMR光谱。分别通过Job图和非线性最小二乘拟合法确定了手性化合物与客体分子的每个对映体的摩尔比和缔合常数。作业图表明主机与所有来宾形成1：1即时复合体。受体对外消旋客体的对映体表现出不同的手性识别能力。在这项研究中使用的手性受体中，脯氨酰胺6被认为是最好的手性转移试剂，对于确定手性羧酸的对映异构体过量有效。手性，2011年。©2011 Wiley‐Liss，Inc.。

  DOI：

  10.1002/chir.20948
• 作为产物：
  描述：

  Boc-L-Pro-indoline 在 lithium aluminium tetrahydride 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (S)-1-methyl-2-[(indolinyl)methyl]pyrrolidine
  参考文献：
  名称：

  Chiral Lewis Acid Controlled Synthesis (CLAC Synthesis): Chiral Lewis Acids Influence the Reaction Course in Asymmetric Aldol Reactions for the Synthesis of Enantiomeric Dihydroxythioester Derivatives in the Presence of Chiral Diamines Derived from L-Proline

  摘要：

  AbstractBoth enantiomers of 2,3‐dihy‐droxythioester derivatives were prepared with almost perfect stereochemical control by chiral Lewis acid controlled synthesis (CLAC synthesis). CLAC synthesis means synthesis of all individual diastereomers or enantiomers from the same starting materials by designing chiral Lewis acids. For example, (Z)‐1‐ethyl‐thio‐1‐(trimethylsiloxy)‐2‐(tert‐butyldi‐methylsiloxy)ethene (1) reacted with aldehydes in the presence of chiral tin(II) Lewis acids using (S)‐1‐methyl‐2‐[(isoin‐dolinyl)methyl]pyrrolidine (4) and (S)‐1‐methyl‐2‐[(indolinyl)methyl]pyrrolidine (5) to afford enantiomeric dihydroxy‐thioester derivatives. Chiral diamines 4 and 5, which were readily prepared from L‐proline, differ only in the fusion point of the benzene ring connected to the pyrrolidine moiety. The unique selectivities were ascribed to the conformational difference between the chiral tin(II) Lewis acids of chiral diamines 4 and 5, and the function of chiral sources for obtaining high selectivities has also been clarified.

  DOI：

  10.1002/chem.19970030914
• 作为试剂：
  描述：

  (Z)-1-(ethylthio)-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene 、 丙醛 在 tin(II) trifluoromethanesulfonate 、 二乙酸二丁基锡 、 (S)-1-methyl-2-[(indolinyl)methyl]pyrrolidine 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 以63%的产率得到S-ethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-hydroxypentanethioate
  参考文献：
  名称：

  Chiral Lewis Acid Controlled Synthesis (CLAC Synthesis): Chiral Lewis Acids Influence the Reaction Course in Asymmetric Aldol Reactions for the Synthesis of Enantiomeric Dihydroxythioester Derivatives in the Presence of Chiral Diamines Derived from L-Proline

  摘要：

  AbstractBoth enantiomers of 2,3‐dihy‐droxythioester derivatives were prepared with almost perfect stereochemical control by chiral Lewis acid controlled synthesis (CLAC synthesis). CLAC synthesis means synthesis of all individual diastereomers or enantiomers from the same starting materials by designing chiral Lewis acids. For example, (Z)‐1‐ethyl‐thio‐1‐(trimethylsiloxy)‐2‐(tert‐butyldi‐methylsiloxy)ethene (1) reacted with aldehydes in the presence of chiral tin(II) Lewis acids using (S)‐1‐methyl‐2‐[(isoin‐dolinyl)methyl]pyrrolidine (4) and (S)‐1‐methyl‐2‐[(indolinyl)methyl]pyrrolidine (5) to afford enantiomeric dihydroxy‐thioester derivatives. Chiral diamines 4 and 5, which were readily prepared from L‐proline, differ only in the fusion point of the benzene ring connected to the pyrrolidine moiety. The unique selectivities were ascribed to the conformational difference between the chiral tin(II) Lewis acids of chiral diamines 4 and 5, and the function of chiral sources for obtaining high selectivities has also been clarified.

  DOI：

  10.1002/chem.19970030914

文献信息

• Application of L-proline derivatives as chiral shift reagents for enantiomeric recognition of carboxylic acids
  作者：Hayriye Nevin Naziroglu、Mustafa Durmaz、Selahattin Bozkurt、Abdulkadir Sirit

  DOI：10.1002/chir.20948

  日期：2011.7

  complexes with all guests. The receptors exhibited different chiral recognition abilities toward the enantiomers of racemic guests. Among the chiral receptors used in this study, prolinamide 6 was found to be the best chiral shift reagent and is effective for the determination of the enantiomeric excess of chiral carboxylic acids. Chirality, 2011. © 2011 Wiley‐Liss, Inc.

  四脯氨酸衍生的手性受体5，6，7，8分别容易地合成从开始大号脯氨酸。手性受体的对映体识别能力用一系列羧酸按11 H NMR光谱。分别通过Job图和非线性最小二乘拟合法确定了手性化合物与客体分子的每个对映体的摩尔比和缔合常数。作业图表明主机与所有来宾形成1：1即时复合体。受体对外消旋客体的对映体表现出不同的手性识别能力。在这项研究中使用的手性受体中，脯氨酰胺6被认为是最好的手性转移试剂，对于确定手性羧酸的对映异构体过量有效。手性，2011年。©2011 Wiley‐Liss，Inc.。
• Chiral Lewis Acid Controlled Synthesis (CLAC Synthesis): Chiral Lewis Acids Influence the Reaction Course in Asymmetric Aldol Reactions for the Synthesis of Enantiomeric Dihydroxythioester Derivatives in the Presence of Chiral Diamines Derived from L-Proline
  作者：Shū Kobayashi、Mineko Horibe

  DOI：10.1002/chem.19970030914

  日期：1997.9

  AbstractBoth enantiomers of 2,3‐dihy‐droxythioester derivatives were prepared with almost perfect stereochemical control by chiral Lewis acid controlled synthesis (CLAC synthesis). CLAC synthesis means synthesis of all individual diastereomers or enantiomers from the same starting materials by designing chiral Lewis acids. For example, (Z)‐1‐ethyl‐thio‐1‐(trimethylsiloxy)‐2‐(tert‐butyldi‐methylsiloxy)ethene (1) reacted with aldehydes in the presence of chiral tin(II) Lewis acids using (S)‐1‐methyl‐2‐[(isoin‐dolinyl)methyl]pyrrolidine (4) and (S)‐1‐methyl‐2‐[(indolinyl)methyl]pyrrolidine (5) to afford enantiomeric dihydroxy‐thioester derivatives. Chiral diamines 4 and 5, which were readily prepared from L‐proline, differ only in the fusion point of the benzene ring connected to the pyrrolidine moiety. The unique selectivities were ascribed to the conformational difference between the chiral tin(II) Lewis acids of chiral diamines 4 and 5, and the function of chiral sources for obtaining high selectivities has also been clarified.