(4S)-3-[(E)-2-methyloct-2-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one | 303142-79-2

• 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: (4S)-3-[(E)-2-methyloct-2-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 303142-79-2
• 化学式: C₁₅H₂₅NO₃
• 分子量: 267.368
• InChiKey: YHVQPSUTWQCWGO-CNELAYHGSA-N

物化性质

• 沸点：
  340.8±25.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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-[(E)-2-methyloct-2-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one 在 lithium aluminium tetrahydride 、 草酰氯 、 sodium hexamethyldisilazane 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 (E,2S)-2-methyl-2-(phenylmethoxymethyl)oct-3-enal
  参考文献：
  名称：

  Novel stereoselective construction of a quaternary carbon: application to synthesis of the cyclopentenedione moiety of madindolines

  摘要：

  Enantioselective synthesis of the cyclopentenedione moiety of madindolines was achieved. Stereoselective construction of a quaternary carbon was realized by alkylation of an enolate possessing chiral auxiliary. Cyclopentenedione was derived from a triketone precursor by intramolecular condensation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00937-0
• 作为产物：
  描述：

  (E)-2-methyloct-2-enoic acid 在 正丁基锂 、 氯化亚砜 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.0h， 生成 (4S)-3-[(E)-2-methyloct-2-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Novel stereoselective construction of a quaternary carbon: application to synthesis of the cyclopentenedione moiety of madindolines

  摘要：

  Enantioselective synthesis of the cyclopentenedione moiety of madindolines was achieved. Stereoselective construction of a quaternary carbon was realized by alkylation of an enolate possessing chiral auxiliary. Cyclopentenedione was derived from a triketone precursor by intramolecular condensation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00937-0

文献信息

• Stereoselective construction of a quaternary carbon substituted with multifunctional groups: application to the concise synthesis of (+)-ethosuximide
  作者：Tomoaki Abe、Tatsuo Suzuki、Kazuhiko Sekiguchi、Seijiro Hosokawa、Susumu Kobayashi

  DOI：10.1016/j.tetlet.2003.10.081

  日期：2003.12

  Synthetically useful β,γ-unsaturated carbonyl compounds having a quaternary carbon at the α-position were prepared with high stereoselectivity by the reaction of a dienolate anion derived from α,β-unsaturated imide having a chiral auxiliary and electrophiles (ethyl acetate and allyl iodide as the C2 and C3 unit, respectively). This method was applied to a short asymmetric synthesis of (+)-ethosuximide

  通过衍生自具有手性助剂的α，β-不饱和酰亚胺的二烯酸根阴离子与亲电子试剂（乙酸乙酯和烯丙基碘）的反应，以高立体选择性制备合成有用的在α-位具有季碳的β，γ-不饱和羰基化合物分别为C 2和C 3单位）。该方法被用于短的不对称合成（+）-ethosuximide。
• 1,3-Rearrangement of ketene-N,O-acetals
  作者：Tatsuo Suzuki、Masaharu Inui、Seijiro Hosokawa、Susumu Kobayashi

  DOI：10.1016/s0040-4039(03)00610-5

  日期：2003.4

  Ketene N,O-acetals were prepared stereoselectively and submitted to a Lewis acid-mediated 1,3-rearrangement to afford C-alkylated products. The reactions proceeded in a stereoselective manner to construct a chiral quaternary carbon in high selectivity. The stereochemistry of the quaternary center was found to be opposite to that obtained by an anionic direct dienolate alkylation.

  立体选择性地制备酮N，O-乙缩醛，并使其经受路易斯酸介导的1，3-重排，得到C-烷基化产物。反应以立体选择性方式进行，以高选择性构建手性季碳。发现季中心的立体化学与通过阴离子直接二烯酸酯烷基化获得的立体化学相反。