2-chloro-N-((1S)-1-phenylethyl)acetamide | 36293-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-N-((1S)-1-phenylethyl)acetamide
• 英文别名: (S)-2-chloro-N-(1-phenylethyl)acetamide；2-chloro-N-[(S)-methylbenzyl]ethanamide；2-chloro-N-[(1S)-1-phenylethyl]acetamide
• CAS: 36293-01-3
• 化学式: C₁₀H₁₂ClNO
• mdl: MFCD00040691
• 分子量: 197.664
• InChiKey: NCGMICUPYDDHPQ-QMMMGPOBSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  360.8±35.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-chloro-N-((1S)-1-phenylethyl)acetamide 在 正丁基锂 、 sodium carbonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 、 丙酮 为溶剂， 反应 21.0h， 生成 (3R)-<3-methyl-1,4-bis(S)-1-phenylethyl>-piperazine-2,5-dione
  参考文献：
  名称：

  Diastereoselective alkylation of (3S)- and (3R)-3-methylpiperazine-2,5-dione derivatives. A convenient approach to both (S)- and (R)-alanine

  摘要：

  Treatment of (3S)-3-methylpiperazine-2,5-dione 6a with LHDMS followed by alkylation of the corresponding enolate with methyl iodide affords (3S,6S)-3,6-dimethyl derivative 7 in 98% de. The same reaction sequence carried out on (3R)-derivative 6b leads to a 93:7 diastereomeric mixture of (3R,6R)-8a and (3R,6S)-8b. Cleavage of the heterocyclic ring of 7 and ga with 57% HI leads to (S)- and (R)-alanine, respectively. The configuration at C-3 (of 6a and 6b) and at C-6 (of 7 and 8a) can be assigned on the basis of H-1 NMR spectroscopy and conformational analysis performed by MMPMI.

  DOI：

  10.1021/jo00050a030
• 作为产物：
  描述：

  Benzenemethanamine, N-(1-phenylethylidene)-, (E)- 在 去甲麻黄碱 、 三乙胺 、 diborane(6) 作用下， 以 苯 为溶剂， 反应 2.5h， 生成 2-chloro-N-((1S)-1-phenylethyl)acetamide
  参考文献：
  名称：

  Laczkowski, Krzysztof Z., Acta poloniae pharmaceutica, 2013, vol. 70, # 2, p. 237 - 244

  摘要：

  DOI：

文献信息

• Effective and efficient sensitisation of terbium luminescence at 355 nm with cell permeable pyrazoyl-1-azaxanthone macrocyclic complexes
  作者：Craig P. Montgomery、David Parker、Laurent Lamarque

  DOI：10.1039/b709805g

  日期：——

  Emissive terbium complexes, suitable for protein conjugation, incorporating a pyrazoyl-1-aza-xanthone chromophore have been prepared; they exhibit cellular uptake and possess a much lower sensitivity to excited state quenching.

  发射性铽配合物，适用于蛋白质共价结合，其包含吡唑啉基-1-氮杂咕吨染料发色团，已成功制备；它们展现细胞摄取能力，并具有较低的激发态淬灭敏感性。
• Emissive and Cell-Permeable 3-Pyridyl- and 3-Pyrazolyl-4-azaxanthone Lanthanide Complexes and Their Behaviour<i>in cellulo</i>
  作者：Craig P. Montgomery、Elizabeth J. New、Lars O. Palsson、David Parker、Andrei S. Batsanov、Laurent Lamarque

  DOI：10.1002/hlca.200900122

  日期：2009.11

  seven emissive europium(III) and terbium(III) complexes was prepared, incorporating a 3‐pyridyl‐4‐azaxanthone or 3‐pyrazolyl‐4‐azaxanthone sensitising moiety within a polydentate macrocyclic ligand. High overall emission quantum yields in aqueous media are attenuated in the presence of protein or certain oxy anions due to displacement of the N,N′‐chelated sensitiser. Nevertheless, these complexes are

  制备了一系列七个发射性euro（III）和b（III）配合物，在多齿大环配体中结合了3-吡啶基-4-氮杂蒽酮或3-吡唑基-4-氮杂蒽酮敏化部分。由于N，N'螯合的敏化剂的置换，在蛋白质或某些氧阴离子存在下，水性介质中较高的总发射量子产率会降低。然而，这些复合物被带入细胞并倾向于在线粒体的最初几个小时内定位，然后被运至内体区室。在存在竞争性抑制剂或定义明确的摄取途径的启动子的情况下，细胞摄取研究揭示了涉及巨胞饮作用的常见摄取机制。
• [EN] PYRIDYL-AZA(THIO)XANTHONE SENSITIZER COMPRISING LANTHANIDE(III) ION COMPLEXING COMPOUNDS, THEIR LUMINESCENT LANTHANIDE (III) ION COMPLEXES AND USE THEREOF AS FLUORESCENT LABELS.<br/>[FR] SENSIBILISATEUR PYRIDYL-AZA(THIO)XANTHONE COMPRENANT DES COMPOSÉS COMPLEXANT LES IONS LANTHANIDE(III), LEURS COMPLEXES DES IONS LANTHANIDE(III) LUMINESCENTS ET LEUR UTILISATION COMME MARQUEURS FLUORESCENTS
  申请人：CIS BIO INT

  公开号：WO2010084090A1

  公开（公告）日：2010-07-29

  Lanthanide (III) Ion completing compound comprising: (1) a sensitizer moiety of Formula (I) in which: a is an integer from 1 to 4; b is an integer equal to 1 or 2; c is an integer equal to 1 or 2; (R1)a, (R2)b, (R3)C are the same or different and are chosen from the group consisting of H; alkyl; -COOR4 where R4 is H or an alkyl; aryl; heteroaryl; saturated or unsaturated cyclic hydrocarbon; CF3; CN; a halogen atom; L-Rg; L-Sc; or two consecutive R3, two consecutive R2 or two consecutive R1 groups together form an aryl or a heteroaryl group or a saturated or unsaturated cyclic hydrocarbon group; where L is a linker, Rg is a reactive group and Sc is a conjugated substance; X1 and X2 are the same or different and are O or S; A is either a direct bond or a divalent group chosen from -CH2- or -(CH2)2-, said moiety being covalentiy attached to (2) a lanthanide (in) ion chelating moiety through A. The above compounds are used in the preparation of luminescent lanthanide (III) ion complexes which are used as fluorescent labels.

  镧系（III）离子配合物包括：（1）式（I）中的感光团，其中：a是1到4之间的整数；b是等于1或2的整数；c是等于1或2的整数；（R1）^a，（R2）^b，（R3）^c相同或不同，并选自H；烷基；-COOR4，其中R4为H或烷基；芳基；杂芳基；饱和或不饱和环烃；CF3；CN；卤原子；L-Rg；L-Sc；或两个连续的R3，两个连续的R2或两个连续的R1组成芳基或杂芳基或饱和或不饱和环烃基；其中L是连接物，Rg是反应性基团，Sc是共轭物质；X1和X2相同或不同，为O或S；A是直接键或从-CH2-或-(CH2)2-中选择的二价基团，所述团通过A与（2）中的镧系（III）离子螯合团结合。上述化合物用于制备发光的镧系（III）离子配合物，用作荧光标记剂。
• [EN] LANTHANIDE (III) ION COMPLEXING COMPOUNDS, LUMINESCENT LANTHANIDE (III) ION COMPLEXES AND USE THEREOF AS FLUORESCENT LABELS<br/>[FR] COMPOSÉS COMPLEXANT LES IONS LANTHANIDE (III), COMPLEXES LUMINESCENTS D'IONS LANTHANIDE (III) ET LEUR UTILISATION COMME MARQUEURS FLUORESCENTS
  申请人：CIS BIO INT

  公开号：WO2009010580A1

  公开（公告）日：2009-01-22

  Lanthanide (III) ion complexing compound comprising: (1) a sensitizer moiety of formula (I) in which: a is an integer from 1 to 4; b is an integer equal 1 or 2; c is an integer equal to 1 or 2; (R1)a, (R2)b, (R3)C are the same or different and are chosen from the group consisting of: H; alkyl; -COOR4 where R4 is H or an alkyl; aryl; heteroaryl; saturated or unsaturated cyclic hydrocarbon; CF3; CN; a halogen atom; L-Rg; L-Sc; or two consecutive R3, two consecutive R2 or two consecutive R1 groups together form an aryl or a heteroaryl group or a saturated or unsaturated cyclic hydrocarbon group; where L is a linker, Rg is a reactive group and Sc is a conjugated substance; X1 and X2 are the same or different and are O or S; A is either a direct bond or a divalent group chosen from -CH2- or -(CH2)2-, said moiety being covalently attached to (2) a lanthanide (III) ion chelating moiety through A. Application: Preparation of luminescent lanthanide (III) ion complexes and use thereof as fluorescent labels.

  镧系（III）离子络合物，包括：（1）具有以下式（I）的感光基团，其中：a是1到4之间的整数；b是等于1或2的整数；c是等于1或2的整数；（R1）^a，（R2）^b，（R3）^c相同或不同，并选自以下群体：H；烷基；-COOR4，其中R4为H或烷基；芳基；杂环芳基；饱和或不饱和环烃；CF3；CN；卤原子；L-Rg；L-Sc；或两个连续的R3，两个连续的R2或两个连续的R1基团共同形成芳基或杂环芳基或饱和或不饱和环烃基团；其中L是连接物，Rg是反应性基团，Sc是共轭物质；X1和X2相同或不同，为O或S；A是直接键或从-CH2-或-(CH2)2-中选择的二价基团，所述基团通过A与（2）具有配位基团的镧系（III）离子共价连接。应用：制备发光的镧系（III）离子络合物并将其用作荧光标记剂。
• Using chiral ionic liquid additives to enhance asymmetric induction in a Diels–Alder reaction
  作者：P. Goodrich、H. Q. Nimal Gunaratne、L. Hall、Y. Wang、L. Jin、M. J. Muldoon、A. P. C. Ribeiro、A. J. L. Pombeiro、V. I. Pârvulescu、P. Davey、C. Hardacre

  DOI：10.1039/c6dt04572c

  日期：——

  ligand has been complexed using Cu(II) and Zn(II) trifluoromethanesulfonate and a range of chiral ionic liquid (CIL) additives based on natural products were used as a co-catalyst for a Diels–Alder reaction. The catalytic performance of these systems was compared for the asymmetric Diels–Alder reaction between N-acryloyloxazolidinone and cyclopentadiene with and without the presence of a CIL additive

  使用三氟甲烷磺酸铜（II）和锌（II）络合了双恶唑啉配体，并且将一系列基于天然产物的手性离子液体（CIL）添加剂用作Diels-Alder反应的助催化剂。比较了在有或没有CIL添加剂的情况下，N-丙烯酰基恶唑烷酮与环戊二烯之间的不对称Diels-Alder反应，比较了这些系统的催化性能。在没有CIL的情况下，两种催化剂在常规溶剂和离子液体中均导致低对映选择性。然而，尽管对于铜基催化剂仅观察到了CIL的微小影响，但对于锌基催化剂而言，内吸力的显着提高 添加CIL时，对映选择性高达50％。