(4R,2''S)-4-benzyl-3[2,4-dimethylpent-4-enoyl]oxazolidin-2-one | 480441-20-1

• 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: (4R,2''S)-4-benzyl-3[2,4-dimethylpent-4-enoyl]oxazolidin-2-one
• 英文别名: (R)-4-bnzyl-3-((S)-2,4-dimethylpent-4-enoyl)oxazolidin-2-one；(4R)-4-benzyl-3-[(2S)-2,4-dimethylpent-4-enoyl]-1,3-oxazolidin-2-one
• CAS: 480441-20-1
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: GNBMVUNINFOGDN-DZGCQCFKSA-N

物化性质

• 沸点：
  434.8±24.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  (4R,2''S)-4-benzyl-3[2,4-dimethylpent-4-enoyl]oxazolidin-2-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以90%的产率得到(S)-2,4-dimethylpent-4-en-1-ol
  参考文献：
  名称：

  The synthesis of 3-hydroxy-2,4,8-trimethyldec-8-enolides and an approach to 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide

  摘要：

  报道了对3、(E)-8、(Z)-8、20a和20b进行对映选择性合成，其中关键步骤是RCM。根据光谱差异，已将天然产物的结构修订为γ-丁内酯。

  DOI：

  10.1039/c4ob01792g
• 作为产物：
  描述：

  3-碘-2-甲基丙-1-烯 、 (R)-(-)-4-苄基-3-丙酰基-2-恶唑烷酮 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 以82%的产率得到(4R,2''S)-4-benzyl-3[2,4-dimethylpent-4-enoyl]oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of the C(7)-C(20) Fragment of Spirotoamides A, B and C

  摘要：

  This work describes the preparation of the C(7)-C(20) fragment of spirotoamides A to C in a very elegant fashion, achievement very high levels of stereocontrol. The synthesis has been accomplished by a sequence involving 14 steps (0.36% overall yield, average of 81% for each step) in high diastereo and enantioselectivity, employing, as determining steps, asymmetric Mukaiyama and boron-mediated 1,5-anti promoted aldol reactions between alpha-methyl-beta-hydroxyketones and aldehydes.

  DOI：

  10.21577/0103-5053.20190126

文献信息

• A chirally catalysed ene reaction in a novel formal total synthesis of the antitumor agent laulimalide
  作者：Michael R Pitts、Johann Mulzer

  DOI：10.1016/s0040-4039(02)02086-5

  日期：2002.11

  A short highly efficient synthesis of the C3C16 fragment 2 of laulimalide 1 is described. Fragment 2 was a key intermediate in a previous approach and thus constitutes a formal total synthesis with improved efficiency. The key steps are an Evans’ alkylation, a Brown allylation and a chirally catalysed stereocontrolled ene-reaction.

  描述了劳来那肽1的C3C16片段2的短时高效合成。片段2是先前方法中的关键中间体，因此构成了具有改进效率的正式总合成。关键步骤是埃文斯烷基化，布朗烯丙基化和手性催化的立体控制烯反应。
• The synthesis of 3-hydroxy-2,4,8-trimethyldec-8-enolides and an approach to 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide
  作者：J. M. Botubol-Ares、M. J. Durán-Peña、A. J. Macías-Sánchez、J. R. Hanson、I. G. Collado、R. Hernández-Galán

  DOI：10.1039/c4ob01792g

  日期：——

  The enantioselective synthesis of 3, (E)-8, (Z)-8, 20a and 20b is reported using RCM as key step. Based in spectroscopic differences, the structure assigned to the natural product has been revised to that of a γ-butyrolactone.

  报道了对3、(E)-8、(Z)-8、20a和20b进行对映选择性合成，其中关键步骤是RCM。根据光谱差异，已将天然产物的结构修订为γ-丁内酯。
• Synthetic routes to the stereoisomers of 2,4-dimethylpentane-1,5-diol derivatives
  作者：Gemma Mas、Lluı̈sa González、Jaume Vilarrasa

  DOI：10.1016/j.tetlet.2003.09.199

  日期：2003.12

  Five different routes to every stereoisomer of non-symmetric derivatives of 2,4-dimethylpentanedioic acid and/or of O-monoprotected 2.4-dimethylpentane-1,5-diols, which are common building blocks for the total synthesis of many polypropionates. have been investigated. Alkylation of the lithium enolate of N-propanoylpseudoephedrine turned out to be the most appropriate method. in connection with the synthesis of fragment C1-C5 of amphidinolide K. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of the C1-C7 and C8-C18 Segments of ent-Amphidinin A
  作者：Jun'ichi Kobayashi、Haruaki Ishiyama、Masahiro Hangyou、Ayumi Nakatsu、Yuta Mori

  DOI：10.3987/com-14-s(k)107

  日期：——

  A stereoselective synthesis of the C1-C7 and C8-C18 segments of the enantiomer of amphidinin A, a cytotoxic polyketide from the culture cells of a symbiotic marine dinoflagellate Amphidinium sp. (strain Y-5), has been achieved, utilizing sulfone-aldehyde coupling, Sharpless asymmetric dihydroxylation, Katsuki-Sharpless asymmetric epoxidation, and Julia-Kocienski olefination.
• Synthesis of the C(7)-C(20) Fragment of Spirotoamides A, B and C
  作者：Allan Rossini、Luiz Dias

  DOI：10.21577/0103-5053.20190126

  日期：——

  This work describes the preparation of the C(7)-C(20) fragment of spirotoamides A to C in a very elegant fashion, achievement very high levels of stereocontrol. The synthesis has been accomplished by a sequence involving 14 steps (0.36% overall yield, average of 81% for each step) in high diastereo and enantioselectivity, employing, as determining steps, asymmetric Mukaiyama and boron-mediated 1,5-anti promoted aldol reactions between alpha-methyl-beta-hydroxyketones and aldehydes.