(R)-(+)-O-vinyl pantolactone | 207557-91-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (R)-(+)-O-vinyl pantolactone
• 英文别名: (R)-(+)-O-vinylpantolactone；(R)-O-vinylpantolactone；(3R)-3-ethenoxy-4,4-dimethyloxolan-2-one
• CAS: 207557-91-3
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: MSZKOXUHBOFXSO-LURJTMIESA-N

物化性质

• 沸点：
  271.5±33.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-O-vinyl pantolactone 在 四氯化锡 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 {[(1R)-3-((3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yloxy)-3-methoxy-1-phenylpropylcarbamoyl]methyl}carbamic acid benzyl ester
  参考文献：
  名称：

  Access to C-protected β-amino-aldehydes via transacetalization of 6-alcoxy tetrahydrooxazinones and use for pseudo-peptide synthesis

  摘要：

  Efficient access to masked beta-amino-aldehydes was performed starting from 6-alcoxy tetrahydrooxazinone 6a-d (6-ATO). Transacetalization leads to the opening of the cycle to form either unsymmetric acetal 7 or symmetric acetals 16-18. These amino acetals are key compounds, obtained with 99% ee, which can be engaged in efficient peptide coupling. This method could easily provide peptides aldehydes or small amido aldehydes as exemplified with the formal synthesis of ent-Maraviroc. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.002
• 作为产物：
  描述：

  (3R)-3-(1-ethoxyethoxy)-4,4-dimethyloxolan-2-one 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(R)-(+)-O-vinyl pantolactone
  参考文献：
  名称：

  Novel Use of N-Benzoyl-N,O-acetals as N-Acylimine Equivalents in Asymmetric Heterocycloaddition:  An Extended Enantioselective Pathway to β-Benzamido Aldehydes

  摘要：

  For the first time, easily available N-(alpha-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnCl4-promoted heterocycloaddition of (R)-O-vinyl pantolactone. By simple acidic hydrolysis of the crude heteroadducts, new beta-aryl- and beta-alkyl-substituted benzamido aldehydes were thus obtained in good overall yields with high enantioselectivities.

  DOI：

  10.1021/jo0203138

文献信息

• Diastereoselective preparation of novel tetrahydrooxazinones via heterocycloaddition of N-Boc, O-Me-acetals
  作者：Patricia Gizecki、Ramzi Ait Youcef、Céline Poulard、Robert Dhal、Gilles Dujardin

  DOI：10.1016/j.tetlet.2004.10.154

  日期：2004.12

  Under Lewis acid conditions, reaction of N-Boc, O-Me acetals with the (R)-(+)-O-vinyl-pantolactone does not lead to the expected dihydrooxazine, but to the corresponding tetrahydrooxazinone, as a result of the loss of the t-Bu group. A diastereoselective and asymmetrical way to these new heterocyclic compounds is described, together with the first evidence of their ability to undergo N-acylation.

  在路易斯酸条件下，由于损失，N -Boc，O -Me乙缩醛与（R）-（+）- O-乙烯基-泛内酯的反应不会产生预期的二氢恶嗪，但会导致相应的四氢恶嗪酮所述的吨-Bu基。描述了对这些新的杂环化合物的非对映选择性和不对称方式，以及它们经历N酰化能力的第一个证据。
• First Asymmetric Synthesis of a 6-Alkoxy-5,6-dihydro-1,3-oxazine:  A Promising Enantioselective Route to β-Amido Aldehydes
  作者：Patricia Gizecki、Robert Dhal、Loïc Toupet、Gilles Dujardin

  DOI：10.1021/ol991326j

  日期：2000.3.1

  [reaction: see text] The 1,3-oxazine route to enantiopure beta-amido aldehydes was investigated. Heterocycloaddition of the N-acyl imine 1 with (R)-O-vinylpantolactone provided the stable dihydroxazine 4c. High diastereocontrols were observed when using Yb(fod)3-catalyzed or SnCl4-mediated conditions, thus leading after quantitative hydrolysis to (R)-N-benzoyl-3-phenylpropanal with >98% ee.

  [反应：见正文]研究了1,3-恶嗪合成对映体纯的β-酰胺基醛的途径。N-酰基亚胺1与（R）-O-乙烯基泛内酯的杂环加成提供了稳定的二氢恶嗪4c。当使用Yb（fod）3催化或SnCl4介导的条件时，观察到较高的非对映异构控制，因此在定量水解为ee> 98％的（R）-N-苯甲酰基-3-苯基丙醛后会导致高非对映异构。
• Diastereoselective Diels−Alder Reactions of <i>N</i>-Sulfonyl-1-aza-1,3-butadienes with Optically Active Enol Ethers:  An Asymmetric Variant of the 1-Azadiene Diels−Alder Reaction
  作者：Ryan C. Clark、Steven S. Pfeiffer、Dale L. Boger

  DOI：10.1021/ja0571646

  日期：2006.3.1

  room-temperature asymmetric Diels-Alder reaction of N-sulfonyl-1-aza-1,3-butadienes is reported enlisting a series of 19 enol ethers bearing chiral auxiliaries, with many providing highly diastereoselective (endo and facial diastereoselection) reactions, largely the result of an exquisitely organized [4+2] cycloaddition transition state. Three new, readily accessible, and previously unexplored auxiliaries rationally

  据报道，对 N-sulfonyl-1-aza-1,3-butadienes 的室温不对称 Diels-Alder 反应的首次详细研究报告了一系列 19 种带有手性助剂的烯醇醚，其中许多提供了高度的非对映选择性（内和面部非对映选择）反应，主要是精心组织的 [4+2] 环加成过渡态的结果。研究中合理地出现了三种新的、易于获取且以前未探索过的辅助剂，它们提供了显着的选择性（其中两种具有 49:1 的内：外和 48:1 的面部选择性），有望在超出这些细节的系统中发挥作用。
• <i>N</i>-Benzyl Aspartate Nitrones: Unprecedented Single-Step Synthesis and [3 + 2] Cycloaddition Reactions with Alkenes
  作者：Thanh Binh Nguyen、Arnaud Martel、Robert Dhal、Gilles Dujardin

  DOI：10.1021/ol8017243

  日期：2008.10.16

  aspartate nitrones 2, prepared by addition of N-benzylhydroxylamine to dialkyl acetylenedicarboxylates 1, underwent [3 + 2] thermal cycloaddition with a wide range of alkenes to afford isoxazolidines 4 bearing a polyfunctionalized quaternary center. Under these uncatalyzed conditions, the trans stereocontrol observed with vinyl ethers is higher than that obtained with all acyclic activated nitrones reported

  通过将N-苄基羟胺加成到乙炔基二羧酸二烷基酯上而制得的N-苄基天冬氨酸硝酮2，与各种烯烃进行[3 + 2]热环加成，得到带有多官能化季中心的异恶唑烷4。在这些未催化的条件下，用乙烯基醚观察到的反式立体控制要高于迄今为止报道的所有无环活化硝酮的反式立体控制。从衍生自（S）-α-甲基苄基羟胺的手性天冬氨酸硝酮开始，实现了对4型纯加合物的首次不对称接触。
• An Improved Dienophile-Induced Access to Enantiopure 2,4-Dideoxysugar Lactones via Hetero Diels-Alder Reaction: Synthesis of the (+)-Lactone Moiety of Compactin
  作者：Gilles Dujardin、Sandrine Rossignol、Eric Brown

  DOI：10.1055/s-1998-4489

  日期：1998.5