(3S)-1-chloro-3-(dibenzylamino)-2-butanone | 156093-93-5

• 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: (3S)-1-chloro-3-(dibenzylamino)-2-butanone
• 英文别名: (S)-3-dibenzylamino-1-chlorobutan-2-one；(3S)-1-chloro-3-(dibenzylamino)butan-2-one
• CAS: 156093-93-5
• 化学式: C₁₈H₂₀ClNO
• 分子量: 301.816
• InChiKey: BSHLWZYRWUNMMW-HNNXBMFYSA-N

物化性质

• 沸点：
  396.3±32.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S)-1-chloro-3-(dibenzylamino)-2-butanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以83%的产率得到(2R,3S)-3-(Dibenzylamino)-1-chlorobutan-2-ol
  参考文献：
  名称：

  The first direct preparation of chiral functionalised ketones and their synthetic uses

  摘要：

  几乎纯镜像异构体的卤代α-羟基和α-氨基酮分别可以通过O-保护的乳酸盐和三苄基化的丙氨酸制备；同时，氨基酮3g也已高度立体选择性地转化为氨基环氧化物7。

  DOI：

  10.1039/c39940000969
• 作为产物：
  描述：

  L-丙氨酸,N,N-二(苯基甲基)-,苯基甲基酯 以86%的产率得到
  参考文献：
  名称：

  Baruenga Jose, Baragana Beatriz, Alonso Alejandro, Concellon Jose M., J. Chem. Soc. Chem. Commun, (1994) N 8, S 969-970

  摘要：

  DOI：

文献信息

• Samarium-Promoted Asymmetric Aldol-Tishchenko Reaction: Synthesis of Amino Acid-Derived 4-Amino-1,3-diols
  作者：Humberto Rodríguez-Solla、Carmen Concellón、Paula Tuya、Santiago García-Granda、M. Rosario Díaz

  DOI：10.1002/adsc.201100952

  日期：2012.6.18

  A samarium‐mediated novel synthesis of enantiopure 4‐amino‐1,3‐diols is carried out through a samarium‐promoted aldol–Tishchenko reaction starting from chiral α′‐amino‐α‐chloro ketones (derived from natural α‐amino acids) and aldehydes. The process takes place with moderate levels of stereoselectivity and in high yields. A mechanism is proposed to explain these results while the absolute configuration

  a介导的新型对映体4-氨基-1,3-二醇的合成是通过a促进的aldol-Tishchenko反应，从手性α'-氨基-α-氯代酮（衍生自天然α-氨基酸）开始和醛。该过程以中等水平的立体选择性和高产率进行。提出了一种机制来解释这些结果，同时通过X射线分析建立了Aldol–Tishchenko加合物的绝对构型和结构。该方法也已用于合成烯异莫尔，1-脱氧鞘氨醇碱基类似物。
• High Diastereoselective Synthesis of Threo or Erythro Aminoalkyl Epoxides from .alpha.-Amino Acids
  作者：Jose Barluenga、Beatriz Baragana、Jose M. Concellon

  DOI：10.1021/jo00126a019

  日期：1995.10

  alpha-Chloro-alpha'-(dibenzylamino) methylketones 3 are synthesized in enantiomerically pure form starting from alpha-amino acids. Reduction of amino ketones 3 and further epoxidation affords three aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94% and 98%. The synthesis of erythro amino epoxides 9 is also described by reaction of alpha-amino aldehydes 7 with in situ generated (halomethyl)lithium. Amino epoxides 9 were obtained with a diastereoisomeric excess ranging between 91% and 98%.
• The First Synthesis of Enantiopure α-Amino Ketimines and Amino Aziridines
  作者：José M. Concellón、Pablo L. Bernad、Estela Riego、Santiago García-Granda、Ángela Forcén-Acebal

  DOI：10.1021/jo005741x

  日期：2001.4.1

  Chiral l-aminoalkyl chloromethyl ketimines 2 are synthesized in enantiomerically pure form starting from l-aminoalkyl chloromethyl ketones 1 and different amines. Reduction of amino ketimines 2 and subsequent spontaneus cyclization affords aminoalkyl aziridines 3 with high diastereoisomeric excess and without detectable racemization.
• Synthetic Applications of 1-Aminoalkyl Chloromethyl Ketones. Synthesis of Enantiopure 3-Azetidinols and Aminoalkyl Epoxides
  作者：José Barluenga、Beatriz Baragaña、José M. Concellón

  DOI：10.1021/jo9700585

  日期：1997.8.1

  Addition of several organocerium compounds to chiral 1-aminoalkyl chloromethyl ketones 1 affords, after deprotection, enantiomerically pure 3-azetidinols 5. The synthesis of enantiopure amino epoxides 8 is also described by successive treatment of chiral alpha-amino ketones 1 with organocerium compounds and methyllithium.
• Preparation and Synthetic Applications of Enantiopure (2<i>S</i>,3<i>S</i>)- or (2<i>R</i>,3<i>S</i>)-2-Halomethyl-1,2-epoxyalkan-3-amines
  作者：José Barluenga、Beatriz Baragaña、José M. Concellón

  DOI：10.1021/jo9823590

  日期：1999.4.1

  Enantiomerically pure (2S,3S)-3 and its diastereoisomer (2R,3S)-2-halomethyl-1,2-epoxyalkan-3-amine 4 have been obtained from 1-aminoalkyl halomethyl ketones 1 and (iodomethyl)lithium or (chloromethyl)lithium, respectively. Some synthetic applications of compounds 3 are described: chiral unsaturated 1,3-aminoalcohols 8 or 2-(halomethylidene)-3-(dibenzylamino)-alkan-1-ol 11 is obtained from 3 by halogeno-lithium or by hydrogen-lithium exchange, respectively. Transformation of 8c into its methyl ester derivative 9c is also reported.