(S)-tert-butyl 4-acryloyl-2,2-dimethyloxazolidine-3-carboxylate | 1401216-98-5

• 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: (S)-tert-butyl 4-acryloyl-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: tert-butyl (4S)-2,2-dimethyl-4-prop-2-enoyl-1,3-oxazolidine-3-carboxylate
• CAS: 1401216-98-5
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: HRJIAJVHCKPEDE-VIFPVBQESA-N

物化性质

• 沸点：
  342.3±42.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 4-acryloyl-2,2-dimethyloxazolidine-3-carboxylate 在 咪唑 、 4-二甲氨基吡啶 、 zinc(II) tetrahydroborate 、 四丁基氟化铵 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 生成 erytho-(4S,2'S)-N-tert-butoxycarbonyl-2,2-dimethyl-4-(oxiran-2'-yl)oxazolidine
  参考文献：
  名称：

  Synthesis of vitamin D3 derivatives with nitrogen-linked substituents at A-ring C-2 and evaluation of their vitamin D receptor-mediated transcriptional activity

  摘要：

  一系列新型 1α,25-二羟基维生素 D3 (1,25-VD3) 衍生物的结合，在 A 环的 2α- 或 2β- 位（2-N-取代的化合物）具有氮连接的取代基，通过计算对接研究对维生素 D 受体 (VDR) 进行了研究。通过在 Trost 条件下将 A 环合成子 6 和/或 7 与带有 CD 环的溴亚甲基 5 偶联来合成选定的化合物。 A 环合成子的 2α- 和 2β- 立体异构体是通过在分子的相对末端安装乙烯基和炔丙基，以 L-丝氨酸 (8) 作为单一手性来源合成的。通过在 NIH3T3 细胞中基于荧光素酶的 VDR 转录活性测定来评估所获得的化合物的活性。包含氢键供体的相对较小的取代基，即 NHAc 和 NHM，可有效引发 VDR 转录活性，2β-NHMs-1,25-VD3 (Xa) 显示出最高的活性，比 1,25- 更有效。 VD3。具有大取代基的衍生物没有活性。这些对 1,25-VD3 衍生物结构-活性关系的新见解可能有助于分离 1,25-VD3 的各种生物活性和产生新型候选治疗药物。

  DOI：

  10.1039/c2ob26017d
• 作为产物：
  描述：

  (1S/R)-1-[(4S)-N-(tert-Butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]prop-2-en-1-ol 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以85%的产率得到(S)-tert-butyl 4-acryloyl-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  A diversity oriented synthesis of d - erythro -sphingosine and siblings

  摘要：

  An efficient building block-based synthetic protocol has been developed for the synthesis of 3-keto-sphingoids with various chain lengths using cross metathesis of a Garner's aldehyde-derived alpha,beta-unsaturated ketone as the key step. Stereoselective reduction of the biomimetic precursors thus obtained provided D-elythro-sphingosine and truncated anaogues in good overall yields. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.08.006

文献信息

• Oxidative Heck Vinylation for the Synthesis of Complex Dienes and Polyenes
  作者：Jared H. Delcamp、Paul E. Gormisky、M. Christina White

  DOI：10.1021/ja402891m

  日期：2013.6.12

  We introduce an oxidative Heck reaction for selective complex diene and polyene formation. The reaction proceeds via oxidative Pd(II)/sulfoxide catalysis that retards palladium-hydride isomerizations which previously limited the Heck manifold's capacity for furnishing stereodefined conjugated dienes. Limiting quantities of nonactivated terminal olefins (1 equiv) and slight excesses of vinyl boronic esters (1.5 equiv) that feature diverse functionality can be used to furnish complex dienes and polyenes in good yields and excellent selectivities (generally E:Z = >20:1; internal:terminal = >20:1). Because this reaction only requires prior activation of a single vinylic carbon, improvements in efficiency are observed for synthetic sequences relative to ones featuring reactions that require activation of both coupling partners.
• A diversity oriented synthesis of d - erythro -sphingosine and siblings
  作者：Amrita Ghosh、Shital K. Chattopadhyay

  DOI：10.1016/j.tetasy.2017.08.006

  日期：2017.9

  An efficient building block-based synthetic protocol has been developed for the synthesis of 3-keto-sphingoids with various chain lengths using cross metathesis of a Garner's aldehyde-derived alpha,beta-unsaturated ketone as the key step. Stereoselective reduction of the biomimetic precursors thus obtained provided D-elythro-sphingosine and truncated anaogues in good overall yields. (C) 2017 Elsevier Ltd. All rights reserved.
• Synthesis of vitamin D3 derivatives with nitrogen-linked substituents at A-ring C-2 and evaluation of their vitamin D receptor-mediated transcriptional activity
  作者：Junko Abe、Yu Nagai、Rui Higashikuni、Keisuke Iida、Takatsugu Hirokawa、Hazuki Nagai、Kaichiro Kominato、Toshio Tsuchida、Michiko Hirata、Masaki Inada、Chisato Miyaura、Kazuo Nagasawa

  DOI：10.1039/c2ob26017d

  日期：——

  Binding of a series of novel 1α,25-dihydroxyvitamin D3 (1,25-VD3) derivatives, having a nitrogen-linked substituent at the 2α- or 2β-position of the A-ring (2-N-substituted compounds), with the vitamin D receptor (VDR) was investigated by means of computational docking studies. Selected compounds were synthesized by coupling A-ring synthons 6 and/or 7 with CD-ring-bearing bromomethylene 5 under Trost's conditions. The 2α- and 2β-stereoisomers of the A-ring synthons were synthesized from L-serine (8) as a single chiral source by installing vinyl and propargyl groups at opposite ends of the molecule. The activity of the obtained compounds was evaluated by means of a luciferase-based VDR transcriptional activity assay in NIH3T3 cells. Relatively small substituents incorporating a hydrogen-bonding donor, i.e., NHAc and NHMs, were effective for eliciting VDR transcriptional activity, and 2β-NHMs-1,25-VD3 (Xa) showed the highest activity, being more potent than 1,25-VD3. Derivatives with bulky substituents were inactive. These new insights into the structure–activity relationships of 1,25-VD3 derivatives may be helpful in separating the various biological activities of 1,25-VD3 and in generating novel therapeutic drug candidates.

  一系列新型 1α,25-二羟基维生素 D3 (1,25-VD3) 衍生物的结合，在 A 环的 2α- 或 2β- 位（2-N-取代的化合物）具有氮连接的取代基，通过计算对接研究对维生素 D 受体 (VDR) 进行了研究。通过在 Trost 条件下将 A 环合成子 6 和/或 7 与带有 CD 环的溴亚甲基 5 偶联来合成选定的化合物。 A 环合成子的 2α- 和 2β- 立体异构体是通过在分子的相对末端安装乙烯基和炔丙基，以 L-丝氨酸 (8) 作为单一手性来源合成的。通过在 NIH3T3 细胞中基于荧光素酶的 VDR 转录活性测定来评估所获得的化合物的活性。包含氢键供体的相对较小的取代基，即 NHAc 和 NHM，可有效引发 VDR 转录活性，2β-NHMs-1,25-VD3 (Xa) 显示出最高的活性，比 1,25- 更有效。 VD3。具有大取代基的衍生物没有活性。这些对 1,25-VD3 衍生物结构-活性关系的新见解可能有助于分离 1,25-VD3 的各种生物活性和产生新型候选治疗药物。