N,N-diethyl-N-(((S)-pyrrolidin-2-yl)methyl)amine | 51207-65-9

• 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: N,N-diethyl-N-(((S)-pyrrolidin-2-yl)methyl)amine
• 英文别名: N-ethyl-N-{[(2S)-pyrrolidin-2-yl]methyl}ethanamine；(S)-N-ethyl-N-(pyrrolidin-2-ylmethyl)ethanamine；2-(S)-(N,N-diethylaminomethyl)pyrrolidine；{[(S)-2-pyrrolidinyl]methyl}diethylamine；(S)-2-((diethylamino)methyl)pyrrolidine；(S)-2-[(diethylamino)methyl]pyrrolidine；N-ethyl-N-[[(2S)-pyrrolidin-2-yl]methyl]ethanamine
• CAS: 51207-65-9
• 化学式: C₉H₂₀N₂
• 分子量: 156.271
• InChiKey: SWMHMAUXZINLIQ-VIFPVBQESA-N

物化性质

• 沸点：
  68 °C(Press: 7 Torr)
• 密度：
  0.872±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-N-(((S)-pyrrolidin-2-yl)methyl)amine 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 生成 (2S)-1-(3'-acetylthio-2'-methylpropanoyl)-2-((diethylamino)methyl)pyrrolidine
  参考文献：
  名称：

  Asymmetric induction in the conjugate addition of thioacetic acid to methacrylamides with chiral auxiliaries

  摘要：

  The conjugate addition of thioacetic acid to methacrylamides with chiral C-2-syrnmetric trans-2,5-disubstituted pyrrolidines afforded the addition products in excellent stereoselectivities (>99% de) and good yields (80-90%). The high selectivity was attributed mainly to the steric effect of the chiral auxiliaries. The cyclic nature of the chiral auxiliaries seemed also important for both the stereoselectivity and the reaction rate. Acidic hydrolysis of the adduct containing (2R,5R)-bis(methoxymethyl)pyrrotidine gave (S)-3-mercapto-2-methylpropanoic acid, a key intermediate for captopril, in 98% ee and 96% yield. The chiral auxiliary was recovered in the demethylated form of N-Boc-(2R,3R)-bis(hydroxymethyl)pyrrolidine in 90% yield. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.037
• 作为产物：
  描述：

  L-Prolin-diethylamid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 N,N-diethyl-N-(((S)-pyrrolidin-2-yl)methyl)amine
  参考文献：
  名称：

  Asymmetric Trasformation of Symmetrical Epoxides to Allylic Alcohols by Lithium (S)-2-(N,N-Disubstituted aminomethyl)pyrrolidide

  摘要：

  使用由(S)-2-(N,N-二取代氨基甲基)吡咯烷和丁基锂制备的手性锂胺，研究了对称环氧化物的对映选择性去质子化反应。通过在四氢呋喃（THF）中采用锂(S)-2-(1-吡咯啉甲基)吡咯化锂并加入1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）的条件，从若干环状和非环状环氧化物中获得了具有中等至高度对映体过剩（ee's）（41-92% ee）的手性烯丙醇。

  DOI：

  10.1246/bcsj.63.721
• 作为试剂：
  描述：

  3-chloromethoxy-propyne 、 4-溴甲基苯甲醛 在 六甲基磷酰三胺 、 N,N-diethyl-N-(((S)-pyrrolidin-2-yl)methyl)amine 、 mercury dichloride 、 锌 作用下， 以 乙酸乙酯 、 苯 为溶剂， 以78.1%的产率得到1-[4-(bromomethyl)phenyl]-2-(prop-2-yn-1-yloxy)ethan-1-ol
  参考文献：
  名称：

  1-[（4-（溴甲基）苯基] -2-（prop-2-yn-1-yloxy）乙醇的绝对构型的确定

  摘要：

  摘要氯甲基炔丙基醚与4-（溴甲基）苯甲醛在锌金属和手性配体N-乙基-N -{[（2 S）-吡咯烷-2-基]甲基}乙胺的存在下反应，得到1- [（4-（溴甲基）苯基] -2-（丙-2-炔-1-基氧基）乙醇具有中等收率和高选择性。

  DOI：

  10.1134/s107042802004020x

文献信息

• Asymmetric Trasformation of Symmetrical Epoxides to Allylic Alcohols by Lithium (<i>S</i>)-2-(<i>N</i>,<i>N</i>-Disubstituted aminomethyl)pyrrolidide
  作者：Masatoshi Asami

  DOI：10.1246/bcsj.63.721

  日期：1990.3

  Enantioselective deprotonation of symmetrical epoxides was studied by using chiral lithium amide, prepared from (S)-2-(N,N-disubstituted aminomethyl)pyrrolidine and butyllithium. Chiral allylic alcohols were obtained with moderate to high enantiomeric excesses (ee’s) (41–92% ee) from several cyclic and acyclic epoxides employing lithium (S)-2-(1-pyrrolidinylmethyl)pyrrolidide in tetrahydrofuran (THF) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

  使用由(S)-2-(N,N-二取代氨基甲基)吡咯烷和丁基锂制备的手性锂胺，研究了对称环氧化物的对映选择性去质子化反应。通过在四氢呋喃（THF）中采用锂(S)-2-(1-吡咯啉甲基)吡咯化锂并加入1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）的条件，从若干环状和非环状环氧化物中获得了具有中等至高度对映体过剩（ee's）（41-92% ee）的手性烯丙醇。
• [EN] FUMAGILLOL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES FUMAGILLOL, ET PROCÉDÉS CORRESPONDANTS DE FABRICATION ET D'UTILISATION
  申请人：ZAFGEN INC

  公开号：WO2017027684A1

  公开（公告）日：2017-02-16

  Disclosed herein, in part, are fumagillol compounds and methods of use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making fumagillol compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

  本文披露了富马吉醇化合物及其在治疗医学疾病（如肥胖症）中的用途方法。提供了富马吉醇化合物的药物组合物和制备方法。这些化合物被认为具有对蛋氨酸氨肽酶2的活性。
• Condensed diazepinones, their compositions and methods of use as
  申请人：Dr. Karl Thomae GmbH

  公开号：US04550107A1

  公开（公告）日：1985-10-29

  Disclosed are novel condensed diazepinones of formula I ##STR1## wherein B is a fused ring selected from ##STR2## X is --CH-- or, when B is ortho-phenylene, X can also be nitrogen; A.sub.1 is C.sub.1 -C.sub.2 alkylene; A.sub.2 is C.sub.1 -C.sub.2 when it is in the 2-position relative to the saturated heterocyclic ring nitrogen or a single bond or methylene when it is in the 3- or 4-position; R.sub.1 is C.sub.1 -C.sub.3 alkyl; R.sub.2 is C.sub.1 -C.sub.7 alkyl, optionally hydroxy-substituted on at least one of its second to seventh carbon, or C.sub.3 -C.sub.7 cycloalkyl, optionally hydroxy substituted, or C.sub.3 -C.sub.7 cycloalkylmethyl; or R.sub.1 and R.sub.2 can, together with the nitrogen therebetween, be a 4- to 7-membered saturated monocyclic, heterocyclic ring which can optionally include an oxygen or N--CH.sub.3 ; R.sub.3 is hydrogen, chlorine, or methyl; R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.5 is hydrogen, chlorine or C.sub.1 -C.sub.4 alkyl; and Z is a single bond, oxygen, methylene or 1,2-ethylene; and NR.sub.1 R.sub.2 --N oxides and nontoxic, pharmaceutically acceptable addition salts thereof. Also disclosed are pyrrolobenzodiazepinone intermediates, pharmaceutical compositions containing the condensed diazepinones and methods of using them to treat cardiovascular disorders, particularly bradycardia and bradyarrhythmia.

  揭示了式I的新型缩合二氮杂环酮##STR1##其中B是从##STR2##中选择的融合环；X是--CH--或者当B是邻苯二甲烷时，X也可以是氮；A.sub.1是C.sub.1-C.sub.2烷基；A.sub.2是C.sub.1-C.sub.2，当它相对于饱和杂环环氮位于2位时，或者是单键或亚甲基，当它位于3位或4位时；R.sub.1是C.sub.1-C.sub.3烷基；R.sub.2是C.sub.1-C.sub.7烷基，其至少在第二到第七碳上可选择地被羟基取代，或者是C.sub.3-C.sub.7环烷基，可选择地被羟基取代，或者是C.sub.3-C.sub.7环烷基甲基；或者R.sub.1和R.sub.2可以与其之间的氮一起形成一个4到7成员的饱和单环杂环，可选择地包括氧或N--CH.sub.3；R.sub.3是氢、氯或甲基；R.sub.4是氢或C.sub.1-C.sub.4烷基，R.sub.5是氢、氯或C.sub.1-C.sub.4烷基；Z是单键、氧、亚甲基或1,2-乙烯基；以及NR.sub.1 R.sub.2 --N氧化物和其无毒、药学上可接受的加合盐。还揭示了吡咯苯二氮杂环酮中间体、含有缩合二氮杂环酮的药物组合物以及使用它们治疗心血管疾病，特别是心动过缓和心动过缓性心律失常的方法。
• Copper(I) Halide Promoted Diastereoselective Synthesis of Chiral Propargylamines and Chiral Allenes using 2-Dialkylaminomethylpyrrolidine, Aldehydes, and 1-Alkynes
  作者：Ramani Gurubrahamam、Mariappan Periasamy

  DOI：10.1021/jo302534f

  日期：2013.2.15

  Copper bromide promoted reactions of aldehydes, 1-alkynes, and chiral 2-dialkylaminomethylpyrrolidine at 25 °C give the corresponding chiral propargylamine derivatives in up to 96% yield and 99:1 dr that are readily converted to the corresponding disubstitued chiral allenes in up to 81% yield and 99% ee upon reaction with CuI in dioxane at 100 °C.

  在25°C下，溴化铜促进醛，1-炔烃和手性2-二烷基氨基甲基吡咯烷的反应，可以以高达96％的收率和99：1 dr的速率得到相应的手性炔丙基胺衍生物，这些衍生物很容易转化为相应的被破坏的手性丙二烯在100°C下与CuI在二恶烷中反应后，产率为81％，ee为99％。
• Chemical differentiation of enantiotopic groups: Diastereoselective opening of a prochiral dilactone
  作者：Eckart Deseke、Wolfgang Hoyer、Ekkehard Winterfeldt

  DOI：10.1016/0040-4020(96)00863-0

  日期：1996.11

  Prochiral dilactone 1 has been synthesized and subjected to diastereo-selective nucleophilic opening. The structural features of chiral, enantiomerically pure nucleophiles have been optimized regarding their capability to perform prochiral recognition at dilactone 1. 3-Ketoglutaric mono acid products 2 of dilactone opening, which are versatile building blocks for natural product synthesis, have been

  前手性双内酯1已合成，并经过非对映选择性亲核开放。关于手性，对映体纯的亲核试剂的结构特征，已对其在双内酯1上进行前手性识别的能力进行了优化。二内酯开口的3-酮戊二酸单酸产物2，是天然产物合成的通用组成部分，已经以高达84:16的非对映体比例获得，并通过随后的结晶至97.5：2.5而富集。