(4S)-3-[(3S)-4-methyl-3-phenylpentanoyl]-4-phenyl-1,3-oxazolidin-2-one | 176018-91-0

• 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: (4S)-3-[(3S)-4-methyl-3-phenylpentanoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 176018-91-0
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: JFJWHAKPYJFGEO-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-3-[(3S)-4-methyl-3-phenylpentanoyl]-4-phenyl-1,3-oxazolidin-2-one 在 lithium hydroxide 、 2,4,6-三异丙基苯磺酰叠氮化物 、 双氧水 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.53h， 生成 (2S,3S)-2-azido-3-phenylisohexanoic acid
  参考文献：
  名称：

  Synthesis and conformational features of topographically constrained designer chimeric amino acids: The β-isopropyl phenylalanines

  摘要：

  All four optically pure isomers of the highly conformationally constrained novel chimeric amino acid, beta-isopropylphenylalanine or beta-phenylleucine, were asymmetrically synthesized in five to six steps in 20-25% overall yield. Computer-assisted molecular modeling revealed that the beta-isopropyl group in these chimeric amino acids plays the dominant role in determining the most favorable side chain conformations. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10127-2
• 作为产物：
  描述：

  (2E)-4-methylpent-2-enoic acid 在 正丁基锂 、 copper bromide dimethyl sulfide complex 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 (4S)-3-[(3S)-4-methyl-3-phenylpentanoyl]-4-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis and conformational features of topographically constrained designer chimeric amino acids: The β-isopropyl phenylalanines

  摘要：

  All four optically pure isomers of the highly conformationally constrained novel chimeric amino acid, beta-isopropylphenylalanine or beta-phenylleucine, were asymmetrically synthesized in five to six steps in 20-25% overall yield. Computer-assisted molecular modeling revealed that the beta-isopropyl group in these chimeric amino acids plays the dominant role in determining the most favorable side chain conformations. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10127-2

文献信息

• Asymmetric synthesis of optically pure β-isopropylphenylalanine: A new β-branched unusual amino acid
  作者：Subo Liao、Victor J. Hruby

  DOI：10.1016/0040-4039(96)00091-3

  日期：1996.3

  All four optically pure isomers of a highly conformationally constrained unusual amino acid, β-isopropylphenylalanine, have been asymmetrically synthesized.

  高度构象受限的不寻常氨基酸β-异丙基苯基丙氨酸的所有四个光学纯异构体均已不对称合成。
• Remarkable dependence of the regioselectivity of free radical additions to 3-cinnamoyloxazolidin-2-ones on the stability of the intermediate adduct-radical, electrophilicity of the adding radicals and the conditions for their generation
  作者：Vitali I. Tararov、Nikolai Yu. Kuznetzov、Vladimir I. Bakhmutov、Nikolai S. Ikonnikov、Yuri N. Bubnov、Victor N. Khrustalev、Tatiana F. Saveleva、Yuri N. Belokon

  DOI：10.1039/a701154g

  日期：——

  nucleophilic radicals (Pri) are found to add at 80 °C to the CC bond of 3-(E)-cinnamoyl-4-phenyloxazolidin-2-one 1a and 3-(E)-cinnamoyl-4-benzyloxazolidin-2-one 1b predominantly at the α-position of the bond. While for the CCl3 radical no product of β-addition has been found, for the Pri radical such a path constitutes up to 40% of the whole process at 80 °C. An interplay between the stability of the intermediate

  发现亲电子基团（CCl 3）和亲核基团（Pr i）在80°C时会添加到3-（E）-肉桂酰基-4-苯基恶唑烷-2--2-酮1a和3-（E）-肉桂酰基的C C键上-4-苄基恶唑烷丁-2-酮1b主要位于键的α-位置。对于CCl 3自由基，没有发现β加成的产物，而对于Pr i自由基，这种途径在80°C下占整个过程的40％。调用中间加合物基团的稳定性与进行加成的基团的亲电子性或亲核性之间的相互作用，以使观察合理化。在低温（–23°C）下添加Pr i 自由基成为主要过程（高达75％）。
• Syntheses of highly constrained β-aryl isohexanoic acid derivatives via asymmetric Michael addition
  作者：Subo Liao、Yinglin Han、Wei Qui、Michael Bruck、Victor J. Hruby

  DOI：10.1016/0040-4039(96)01795-9

  日期：1996.10

  A series of enantiomerically pure highly sterically hindered β-branched isohexanoic acid derivatives have been synthesized with high diastereoselectivity via asymmetric Michael addition. The X-ray crystal structure of (4S,3′S)-3-[3′-(2,6-dimethylphenyl)isohexanyl]-4-phenyl-2-oxazolidinone demonstrated that the β-configuration was induced from the Si-face, and that the torsional angle χ2 was restricted

  已经通过不对称迈克尔加成以高非对映选择性合成了一系列对映体纯的高空间位阻的β-支化异己酸衍生物。（4S，3′S）-3- [3′-（2，6-二甲基苯基）异己基] -4-苯基-2-恶唑烷酮的X射线晶体结构表明，β-构型是由Si-诱导的。面，并且所述扭转角χ 2由笨重β-异丙基限制为从分子建模预期的范围内。