(4S)-3-allyl-4-hydroxymethyl-oxazolidin-2-one | 171253-67-1

• 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: (4S)-3-allyl-4-hydroxymethyl-oxazolidin-2-one
• 英文别名: (4S)-4-(hydroxymethyl)-3-prop-2-enyl-1,3-oxazolidin-2-one
• CAS: 171253-67-1
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: GPGYQPMQPXJRQX-LURJTMIESA-N

物化性质

• 沸点：
  363.3±25.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-3-allyl-4-hydroxymethyl-oxazolidin-2-one 在 Grubbs catalyst first generation 、 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (8S,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one
  参考文献：
  名称：

  通过闭环烯烃复分解合成恶唑烷二氮杂环化合物：脱氧天竺葵和羟基吡咯烷核苷合成的实际入口

  摘要：

  从d-和l-丝氨酸开始，说明了一种制备恶唑烷二基哌啶，氮杂环庚烷和氮杂环辛烯的简便方法，作为通往各种脱氧天竺葵和羟基吡咯烷核苷的途径。恶唑烷基二烯烃的闭环烯烃复分解用作构建氮杂环的关键步骤。恶唑烷二基氮杂环辛烯的连续环氧化，水解和环过环生成羟基吡咯烷核苷。

  DOI：

  10.1016/s0040-4039(01)00635-9
• 作为产物：
  描述：

  (R)-2-oxooxazolidme-4-carboxylic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以91%的产率得到(4S)-3-allyl-4-hydroxymethyl-oxazolidin-2-one
  参考文献：
  名称：

  构象受限的海藻酸类似物的合成。类胡萝卜素的C4取代基构象对其神经兴奋活性重要吗？

  摘要：

  通过三亚甲基甲烷与α，β-不饱和酯的分子内加成反应，合成了具有氮杂双环[3.3.0]辛烷体系的海藻酸的构象受限的类似物。每种合成的异构体均显示出非常弱的去极化活性。这些结果表明，海藻酸的异丙烯基的平面应与吡咯烷环成对角线，以显示出有效的活性。

  DOI：

  10.1016/0040-4039(95)01094-x

文献信息

• Stereoselective Synthesis of (−)-α-Kainic Acid and (+)-α-Allokainic Acid via Trimethylstannyl-Mediated Radical Carbocyclization and Oxidative Destannylation
  作者：Stephen Hanessian、Sacha Ninkovic

  DOI：10.1021/jo9604088

  日期：1996.1.1

  (-)-alpha-Kainic acid (1) and its C4 epimer (+)-alpha-allokainic acid (2) have been prepared from L-serine. The requisite stereochemical array in (-)-alpha-kainic acid (1) was introduced using a trimethylstannyl radical carbocyclization of a diene, which gave the 2,3-trans/3,4-cis and 2,3-trans/3,4-trans compounds in a 2.8:1 ratio and in high yield. The destannylation of the trisubstituted pyrrolidine nucleus was achieved via an oxidative cleavage of the C-Sn bond with eerie ammonium nitrate. This provided a dimethyl acetal. that was further transformed into the intended alpha-kainic acid. When the same radical carbocyclization was attempted on a triene, the 2,3-trans/3,4-trans and the 2,3-trans/3,4-cis adducts were obtained in a 2.5:1 ratio, respectively. This approach was used to synthesize (+)-alpha-allokainic acid.

  (-)-α-海葵酸（1）及其C4异构体( + )-α-异海葵酸（2）已从L-丝氨酸中制备。在(-)-α-海葵酸（1）中引入了必需的立体化学排列，使用了二烯的三甲基tin基自由基环化反应，该反应以2.8:1的比率和高产率生成2,3-顺式/3,4-顺式和2,3-顺式/3,4-反式的化合物。三元环吡咯烷核心的脱tin化通过使用硝酸铈铵对C-Sn键进行氧化裂解来实现。这提供了一种二甲基乙酰胺，该乙酰胺进一步转化为目标α-海葵酸。当尝试对三烯进行相同的自由基环化时，分别以2.5:1的比率获得2,3-顺式/3,4-反式和2,3-顺式/3,4-顺式的加成物。这一方法被用于合成( + )-α-异海葵酸。
• A Formal Synthesis of (+)-a-Allokainic Acid via Sulfanyl Radical Addition-Cyclization Reaction
  作者：Takeaki Naito、Okiko Miyata、Yoshiki Ozawa、Ichiya Ninomiya、Keiichi Aoe、Hajime Hiramatsu

  DOI：10.3987/com-97-s18

  日期：——
• Versatile approach for the synthesis of novel seven-membered iminocyclitols via ring-closing metathesis dihydroxylation reaction
  作者：Chang-Ching Lin、Yi-shin Pan、Laxmikant N Patkar、Hsiu-Mei Lin、Der-Lii M Tzou、Thangaiah Subramanian、Chun-Cheng Lin

  DOI：10.1016/j.bmc.2004.03.064

  日期：2004.6

  Seven-membered iminocyclitols with diverse diastereomers were prepared starting with D- and L-serines and employing ring-closing olefin metathesis and dihydroxylation reaction sequence. The iminocyclitols were assayed for glycosidase inhibition and compound 20 was found to be a competitive inhibitor for beta-glucosidase with K-i 26.3 muM. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of oxazolidinyl azacycles via ring-closing olefin metathesis: a practical entry to the synthesis of deoxy-azasugars and hydroxypyrrolizidines
  作者：Thangaiah Subramanian、Chang-Ching Lin、Chun-Cheng Lin

  DOI：10.1016/s0040-4039(01)00635-9

  日期：2001.6

  l-serines, an expedient method for the preparation of oxazolidinyl piperidines, azepenes and azacyclooctenes was illustrated as a route to various deoxy-azasugars and hydroxypyrrolizidines. The ring-closing olefin metathesis of oxazolidinyl di-olefins was used as a key-step to construct the azacycles. Consecutive epoxidation, hydrolysis and transannulation of oxazolidinyl azacyclooctene led to hydroxypyrrolizidines

  从d-和l-丝氨酸开始，说明了一种制备恶唑烷二基哌啶，氮杂环庚烷和氮杂环辛烯的简便方法，作为通往各种脱氧天竺葵和羟基吡咯烷核苷的途径。恶唑烷基二烯烃的闭环烯烃复分解用作构建氮杂环的关键步骤。恶唑烷二基氮杂环辛烯的连续环氧化，水解和环过环生成羟基吡咯烷核苷。
• Synthesis of conformationally restricted analogs of kainic acid. Is the conformation of the C4-substituent of kainoid important to its neuroexcitatory activity?
  作者：Kimiko Hashimoto、Yasufumi Ohfune、Haruhisa Shirahama

  DOI：10.1016/0040-4039(95)01094-x

  日期：1995.8

  restricted analogs of kainic acid, which have an azabicyclo[3.3.0]octane system, were synthesized through the intramolecular addition reaction of trimethylenemethane to the α,β-unsaturated ester. Every synthesized isomer showed very weak depolarizing activity. These results indicate that the plane of the isopropenyl group of kainic acid should be diagonal to the pyrrolidine ring to show potent activity.

  通过三亚甲基甲烷与α，β-不饱和酯的分子内加成反应，合成了具有氮杂双环[3.3.0]辛烷体系的海藻酸的构象受限的类似物。每种合成的异构体均显示出非常弱的去极化活性。这些结果表明，海藻酸的异丙烯基的平面应与吡咯烷环成对角线，以显示出有效的活性。