(3R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-piperidine | 519189-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-piperidine
• 英文别名: (3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-piperidine；tert-butyl-[(3R,5R)-5-[tert-butyl(dimethyl)silyl]oxypiperidin-3-yl]oxy-dimethylsilane
• CAS: 519189-07-2
• 化学式: C₁₇H₃₉NO₂Si₂
• 分子量: 345.673
• InChiKey: IKEVWNDQTXWXNZ-HUUCEWRRSA-N

物化性质

• 沸点：
  341.3±42.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-piperidine 反应 20.0h， 生成 (2S,3R,3aS,4R,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-hexahydro-isoxazolo[2,3-a]pyridine-2,3-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone

  摘要：

  The oxidation of a C-2 symmetric piperidine, obtained through a ring enlargement process of the enantiopure protected (4R)-hydroxy-(2S)-hydroxymethyl pyrrolidine, is reported. Oxidation with C-phenyl-N-phenylsulfonyloxaziridine afforded the corresponding nitrone that is too unstable for isolation and which reacted in situ with dimethyl maleate. The major adduct was transformed to the corresponding protected dihydroxyindolizidinone. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02336-5
• 作为产物：
  描述：

  (2S,4R)-1-benzyl-4-hydroxyproline methyl ester 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、405.3 kPa 条件下， 反应 123.0h， 生成 (3R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-piperidine
  参考文献：
  名称：

  使用（3 R，5 R）-二羟基哌啶衍生物催化剂将芳香族和脂肪族醛中的对映选择性二乙基锌加成

  摘要：

  由反式-4-羟基-1-脯氨酸可方便地制备一系列手性（3 R，5 R）-二羟基哌啶衍生物3a - f，并将其用于催化二乙基锌对苯甲醛和庚醛的对映选择性加成反应。其中，发现3d在促进Et 2 Zn向各种醛的添加中表现出最佳的不对称诱导作用，提供高达98％ee的（R）-仲醇。

  DOI：

  10.1016/j.tet.2005.11.070

文献信息

• [EN] DUAL NK1/NK3 ANTAGONISTS FOR TREATING SCHIZOPHRENIA<br/>[FR] ANTAGONISTES DOUBLES DES RECEPTEURS NK1/NK3 POUR TRAITER LA SCHIZOPHRENIE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2005002577A1

  公开（公告）日：2005-01-13

  The use of compounds of the general formula wherein the substituents are as described in claim 1 or pharmaceutically active acid-addition salts thereof for the preparation of medicaments for the treatment of schizophrenia.

  使用一般式化合物，其中取代基如权利要求1中所述，或其药用活性酸盐，用于制备治疗精神分裂症的药物。
• Dual NK1/NK3 receptor antagonists
  申请人：Hoffmann Torsten

  公开号：US20050090533A1

  公开（公告）日：2005-04-28

  The present invention provides a method for the treatment of schizophrenia which comprises administering a compound of formula wherein the substituents are as described herein or a pharmaceutically active acid-addition salt thereof. In particular, the invention provides methods for treating both positive and negative symptoms of schizophrenia through dual inhibition of NK1 and NK3 receptors. The invention also provides novel compounds with formula I and methods for preparing compounds of the invention.

  本发明提供了一种治疗精神分裂症的方法，包括给予式中所述的取代基如本文所述的化合物或其药物活性酸盐。特别地，本发明提供了通过双重抑制NK1和NK3受体治疗精神分裂症的方法，包括治疗阳性和阴性症状。本发明还提供了具有式I的新化合物以及制备本发明化合物的方法。
• DUAL NK1/NK3 RECEPTOR ANTAGONISTS
  申请人：Hoffmann Torsten

  公开号：US20110178055A1

  公开（公告）日：2011-07-21

  The present invention provides a method for the treatment of schizophrenia which comprises administering a compound of formula wherein the substituents are as described herein or a pharmaceutically active acid-addition salt thereof. In particular, the invention provides methods for treating both positive and negative symptoms of schizophrenia through dual inhibition of NK1 and NK3 receptors. The invention also provides novel compounds with formula I and methods for preparing compounds of the invention.

  本发明提供了一种治疗精神分裂症的方法，该方法包括给予式中所述的取代基如此描述或其药物活性酸加成盐。特别地，本发明通过双重抑制NK1和NK3受体提供了治疗精神分裂症的方法，包括治疗阳性和阴性症状。本发明还提供了式I的新化合物以及制备本发明化合物的方法。
• Enantioselective diethylzinc addition to aromatic and aliphatic aldehydes using (3R,5R)-dihydroxypiperidine derivatives catalyst
  作者：Rémi Roudeau、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1016/j.tet.2005.11.070

  日期：2006.3

  derivatives 3a–f were conveniently prepared from trans-4-hydroxy-l-proline and applied to the catalytic enantioselective addition of diethylzinc to benzaldehyde and heptanal. Among them, 3d was found to show the best asymmetric induction in promoting the addition of Et2Zn to various aldehydes, providing (R)-secondary alcohols in up to 98% ee.

  由反式-4-羟基-1-脯氨酸可方便地制备一系列手性（3 R，5 R）-二羟基哌啶衍生物3a - f，并将其用于催化二乙基锌对苯甲醛和庚醛的对映选择性加成反应。其中，发现3d在促进Et 2 Zn向各种醛的添加中表现出最佳的不对称诱导作用，提供高达98％ee的（R）-仲醇。
• A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone
  作者：Alberto Brandi、Stefano Cicchi、Valentina Paschetta、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1016/s0040-4039(02)02336-5

  日期：2002.12

  The oxidation of a C-2 symmetric piperidine, obtained through a ring enlargement process of the enantiopure protected (4R)-hydroxy-(2S)-hydroxymethyl pyrrolidine, is reported. Oxidation with C-phenyl-N-phenylsulfonyloxaziridine afforded the corresponding nitrone that is too unstable for isolation and which reacted in situ with dimethyl maleate. The major adduct was transformed to the corresponding protected dihydroxyindolizidinone. (C) 2002 Elsevier Science Ltd. All rights reserved.