(2'R,4R)-3-(2'-isopropyl-3'-phenylpropionyl)-4-benzyloxazolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (2'R,4R)-3-(2'-isopropyl-3'-phenylpropionyl)-4-benzyloxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-[(2R)-2-benzyl-3-methylbutanoyl]-1,3-oxazolidin-2-one
• 化学式: C₂₂H₂₅NO₃
• 分子量: 351.445
• InChiKey: OBCAXPYSHXFYIQ-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-cinnamic acid benzyl ester 在 palladium on activated charcoal 盐酸 、 三乙基硅烷 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 氢气 、 N,N'-二环己基碳二亚胺 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 40.5h， 生成 (2'R,4R)-3-(2'-isopropyl-3'-phenylpropionyl)-4-benzyloxazolidin-2-one
  参考文献：
  名称：

  Intermolecular Asymmetric Reductive Aldol Reaction of Ketones as Acceptors Promoted by Chiral Rh(Phebox) Catalyst

  摘要：

  The conjugate reduction of cinnamates with hydrosilane and chiral Rh(Phebox-ip) catalyst in the presence of excess acetone is shown to provide the corresponding intermolecular reductive aldol product in extremely high enantioselectivity (up to 98%). Several cinnamates and crotonate substrates and several ketone acceptors were also examined.

  DOI：

  10.1021/ol070251d

文献信息

• 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％）。
• Fluorination process
  申请人：Gouverneur Veronique

  公开号：US20070142632A1

  公开（公告）日：2007-06-21

  Compounds of formula (II), (IIIa) or (IIIb) (variables are described in the specification) are prepared by fluorination of β,γ-unsaturated alkyl silanes. These compounds are useful as building blocks in the pharmaceutical industry.

  根据说明书中描述的变量，通过对β,γ-不饱和烷基硅烷进行氟化制备出式（II）、（IIIa）或（IIIb）的化合物。这些化合物在制药工业中作为构建模块非常有用。
• US7572928B2
  申请人：——

  公开号：US7572928B2

  公开（公告）日：2009-08-11
• Intermolecular Asymmetric Reductive Aldol Reaction of Ketones as Acceptors Promoted by Chiral Rh(Phebox) Catalyst
  作者：Takushi Shiomi、Hisao Nishiyama

  DOI：10.1021/ol070251d

  日期：2007.4.1

  The conjugate reduction of cinnamates with hydrosilane and chiral Rh(Phebox-ip) catalyst in the presence of excess acetone is shown to provide the corresponding intermolecular reductive aldol product in extremely high enantioselectivity (up to 98%). Several cinnamates and crotonate substrates and several ketone acceptors were also examined.