1-[(S)-(-)-2-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]propan-1-one | 92053-21-9

• 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-[(S)-(-)-2-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]propan-1-one
• 英文别名: 1-<2(S)-(dimethylhydroxymethyl)pyrrolid-1-yl>propanoic acid；(S)-1-<2-(1-Hydroxy-1-methylethyl)pyrrolidin-1-yl>propan-1-on；(S)-(-)-2-(N-Propionylpyrrolidin-2-yl)propan-2-ol；1-[(2S)-2-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]propan-1-one
• CAS: 92053-21-9
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: OLOUSHBSWRRJTD-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(S)-(-)-2-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]propan-1-one 在 四丁基碘化铵 、 sodium hydride 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  Induction of asymmetry by a remote chiral center in the amide acetal Claisen rearrangement

  摘要：

  DOI：

  10.1021/ja00256a026
• 作为产物：
  描述：

  N-benzyl-(S)-proline methyl ester 在 10percent Pd/C 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 20.0~70.0 ℃ 、101.33 kPa 条件下， 反应 72.5h， 生成 1-[(S)-(-)-2-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]propan-1-one
  参考文献：
  名称：

  Synthesis of N-propionylated (S )-(−)-2-(pyrrolidin-2-yl)propan-2-ol and its use as a chiral auxiliary and selectivity marker in asymmetric aldol reactions

  摘要：

  合成了N-丙酰化吡咯烷衍生物和手性辅助剂(S)-(β-)-2-(吡咯烷-2-基)丙醇-2，并在与苯甲醛的立体选择性醛醇反应中使用。通过监测获得的醛醇加合物的¹H NMR光谱，研究了立体选择性在温度、溶剂、螯合剂及使用的螯合剂量上的差异。研究的添加剂中，Cp₂ZrCl₂诱导了更高的反式选择性，而SnCl₂则诱导了更高的顺式选择性。发现TMSCl在高选择性上对一个顺式和一个反式二叠体具有影响。改变钛添加剂的配体组合被发现会导致选择性的差异，其中(i-PrO)₃TiCl表现出顺式选择性，而Cp₂TiCl₂则表现出反式选择性。反应性和立体选择性的差异也发现依赖于所添加的路易斯酸的量。还研究了去除辅助剂的方法。酸水解成功用于获得所需的3-羟基-2-甲基-3-苯基丙酸，但发现产率较低，并导致大量的异构化。此外，这些羟基酸的乙基酯可以通过液相色谱轻易分离为纯的顺式和反式二叠体。

  DOI：

  10.1039/b001730m

文献信息

• Optisch aktive 3-Amino-2H-azirine als Bausteine f�r enantiomerenreine ??-disubstituierte ?-Aminos�uren: Synthese von Isovalin-Synthonen und Einbau in ein Trichotoxin-A-50-Segment
  作者：Christoph B. Bucher、Heinz Heimgartner

  DOI：10.1002/hlca.19960790713

  日期：1996.10.30

  Optically Active 3-Amino-2H-azirines as Synthons for Enantiomerically Pure αα-Disubstiuted α-Amino Acids: Syntheses of Isovaline Synthons and a Segment of Trichotoxin A-50

  旋光性3-氨基-2 H-叠氮基作为对映体纯αα-二取代的α-氨基酸的合成子：异缬氨酸合成子和一部分滴虫毒素A-50的合成
• Guoqiang, Lin; Hjalmarsson, Mats; Hoegberg, Hans-Erik, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1984, vol. 38, # 9, p. 795 - 802
  作者：Guoqiang, Lin、Hjalmarsson, Mats、Hoegberg, Hans-Erik、Jernstedt, Karen、Norin, Torbjoern

  DOI：——

  日期：——
• Highly stereoselective alkylation of (S)-proline-based chiral auxiliaries
  作者：Fredrik Andersson、Erik Hedenström

  DOI：10.1016/j.tetasy.2004.06.045

  日期：2004.8

  Alkylation of the enolates of the propanoylamides of two chiral auxiliaries (S)-(-)-2-(pyrrolidin-2-yl)propan-2-ol 1a and (S)-(-)-2-(2-methoxypropan-2-yl)pyrrolidine 1b, derived from (S)-proline, with benzyl bromide and n-butyl iodide has been studied. The auxiliaries 1a and 1b induced opposite selectivity that is (R)- and (S)-configuration, respectively, at the newly created stereogenic centre. The diastereoselectivities and conversion yields in these alkylations were moderate to excellent. When Cp2ZrCl2 was used as an enolate coordinating agent, benzylation of propanoylated 1b gave an excellent diastereomeric ratio of 99:1. The benzylated diastereomeric products from either propanoylated 1a or 1b were easily separated by liquid chromatography. (C) 2004 Elsevier Ltd. All rights reserved.
• INDUCTION, OF ASYMMETRY BY A REMOTE CHIRAL CENTER IN THE AMIDE ACETAL CLA+, J. AMER. CHEM. SOC., 109,(1987) N 22, 6716-6719
  作者：INDUCTION, OF ASYMMETRY BY A REMOTE CHIRAL CENTER IN THE AMIDE ACETAL CLA+

  DOI：——

  日期：——
• SREBP INHIBITORS COMPRISING A 6-MEMBERED CENTRAL RING
  申请人：Capulus Therapeutics, LLC

  公开号：US20210047340A1

  公开（公告）日：2021-02-18

  Provided herein are compounds comprising a three-ring core, such as compounds of Formula (X), Formula (X-A), Formula (X-Ai), Formula (X-B), Formula (X-Bi), Formula (Z), Formula (Z-A), Formula (Z-Ai), Formula (Z-B), Formula (Z-Bi), Formula (I), Formula (I-A), Formula (I-Ai), Formula (I-B), and Formula (I-Bi), and pharmaceutically acceptable salts, solvates, tautomers, isotopes, or isomers thereof. Also provided herein are methods of inhibiting a component of the sterol regulatory element binding protein (SREBP) pathway, such as an SREBP or SREBP cleavage activating protein (SCAP), using these compounds, or pharmaceutically acceptable salts, solvates, tautomers, isotopes, or isomers thereof. Further provided are methods of treating a disorder in a subject in need thereof, such as liver disease, non-alcoholic steatohepatitis, insulin resistance, or cancer.