(4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one | 391677-98-8

• 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)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one
• 英文别名: (4R)-4-methyl-4-[2-(thiophen-2-yl)ethyl]-1,3-oxazolidin-2-one；(4R)-4-methyl-4-(2-thiophen-2-ylethyl)-1,3-oxazolidin-2-one
• CAS: 391677-98-8
• 化学式: C₁₀H₁₃NO₂S
• 分子量: 211.285
• InChiKey: GXEIFDOEAZITMF-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one 、 D-酒石酸 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙醇 为溶剂， 反应 48.0h， 以99.7%的产率得到(2R)-amino-2-methyl-4-thiophen-2-ylbutan-1-ol 1/2D-(-)-tartrate
  参考文献：
  名称：

  Amino alcohol derivatives

  摘要：

  式（I）的化合物表现出优异的免疫抑制活性，其药理学上可接受的盐，酯或其他衍生物：其中R1和R2是氢原子，氨基保护基；R3是氢原子，羟基保护基；R4是较低的烷基基团；n是1到6之间的整数；X是乙烯基团；Y是C1-C10烷基基团，带有1到3个从取代基a和b中选择的取代基的C1-C10烷基基团；R5是芳基基团；R6和R7是氢原子，从取代基a中选择的基团；但是当R5是氢原子时，Y不是单键或直链的C1-C10烷基基团。

  公开号：

  US20030236297A1
• 作为产物：
  描述：

  (1,3-二羟基-2-甲基-2-丙基)(2-甲基-2-丙基)氨基甲酸 在 palladium on activated charcoal sodium hydroxide 、 4 A molecular sieve 、 immobilized Pseudomonas sp. lipase 、 potassium tert-butylate 、 氢气 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 异丙醚 为溶剂， 反应 3.0h， 生成 (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one
  参考文献：
  名称：

  Enzymatic desymmetrization of 2-amino-2-methyl-1,3-propanediol: asymmetric synthesis of (S)-N-Boc-N,O-isopropylidene-α-methylserinal and (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one

  摘要：

  We report herein, the novel enzymatic desymmetrization of 2-tert-butoxycarbonylamino-2-methyl-1,3-propanediol 1. This method makes it possible to prepare (S)-N-Boc-N,O-isopropylidene-alpha-methylserinal 3, which is a chiral building block for the synthesis of a variety of a-substituted alanine derivatives. Moreover, optically active (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one 4. one of the key intermediates in the synthesis of a novel immunosuppressant, has been prepared by this methodology. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.037

文献信息

• Synthesis of a chiral phosphonium salt for the preparation of α-substituted alaninol derivatives
  作者：Takashi Tsuji、Keisuke Suzuki、Tsuyoshi Nakamura、Takahide Nishi

  DOI：10.1016/j.tet.2014.05.086

  日期：2014.8

  We herein report the synthesis of a chiral phosphonium salt, [(4S)-4-methyl-2-oxo-1,3-oxazolidin-4-yl]methyl}(triphenyl)phosphonium iodide 13 to provide a new Wittig reagent for the general method of synthesizing α-substituted alaninol derivatives. Our method described here is widely applicable to reactions with various types of aldehyde to afford olefin products with high E-selectivity, enabling

  本文我们报告一个手性鏻盐的合成中，[（4-小号）-4-甲基-2-氧代-1,3-恶唑烷-4-基]甲基}（三苯基）碘化鏻13，以提供一个新的维悌希试剂用于合成α-取代的丙氨醇衍生物的一般方法。我们在此描述的方法广泛适用于与各种类型的醛反应，以提供具有高E选择性的烯烃产品，这使我们能够提供一种新的手性S1P 1激动剂合成方法，包括我们的关键中间体以及痕量胺-相关受体1（TAAR1）激动剂。
• Asymmetric synthesis of α,α-disubstituted α-amino alcohol derivatives
  作者：Tsuyoshi Nakamura、Takashi Tsuji、Yukiko Iio、Shojiro Miyazaki、Toshiyasu Takemoto、Takahide Nishi

  DOI：10.1016/j.tetasy.2006.10.007

  日期：2006.10

  We herein report an asymmetric synthesis of alpha,alpha-disubstituted alpha-amino alcohol derivatives 3, key intermediates of a novel immunomodulator, using enzymatic desymmetrization of 2-alkyl-2-tert-butoxycarbonylamino-1,3-propanediols 1a and 1b. This method makes it possible to prepare a chiral analogue of FTY720 4. These synthetic procedures allow for a broad structure variation in order to evaluate structure-activity relationships and the mechanism of action for sphingosine 1-phosphate-1 (SIP1) receptor agonist. (c) 2006 Elsevier Ltd. All rights reserved.
• Enzymatic desymmetrization of 2-amino-2-methyl-1,3-propanediol: asymmetric synthesis of (S)-N-Boc-N,O-isopropylidene-α-methylserinal and (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one
  作者：Takashi Tsuji、Yukiko Iio、Toshiyasu Takemoto、Takahide Nishi

  DOI：10.1016/j.tetasy.2005.07.037

  日期：2005.10

  We report herein, the novel enzymatic desymmetrization of 2-tert-butoxycarbonylamino-2-methyl-1,3-propanediol 1. This method makes it possible to prepare (S)-N-Boc-N,O-isopropylidene-alpha-methylserinal 3, which is a chiral building block for the synthesis of a variety of a-substituted alanine derivatives. Moreover, optically active (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one 4. one of the key intermediates in the synthesis of a novel immunosuppressant, has been prepared by this methodology. (c) 2005 Elsevier Ltd. All rights reserved.
• Amino alcohol derivatives
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20030236297A1

  公开（公告）日：2003-12-25

  Compounds of formula (I) which exhibit excellent immune suppression activity, pharmacologically acceptable salts thereof, esters thereof or other derivatives: 1 wherein R 1 and R 2 are a hydrogen atom, an amino protecting group; R 3 is a hydrogen atom, a hydroxy protecting group; R 4 is a lower alkyl group; n is an integer from 1 to 6; X is an ethylene group; Y is a C 1 -C 10 alkylene group, a C 1 -C 10 alkylene group substituted with 1 to 3 substituents selected from substituent group a and b; R 5 is an aryl group; R 6 and R 7 are a hydrogen atom, a group selected from substituent group a; with the proviso when R 5 is a hydrogen atom, Y is not a single bond or a straight chain C 1 -C 10 alkylene group.

  式（I）的化合物表现出优异的免疫抑制活性，其药理学上可接受的盐，酯或其他衍生物：其中R1和R2是氢原子，氨基保护基；R3是氢原子，羟基保护基；R4是较低的烷基基团；n是1到6之间的整数；X是乙烯基团；Y是C1-C10烷基基团，带有1到3个从取代基a和b中选择的取代基的C1-C10烷基基团；R5是芳基基团；R6和R7是氢原子，从取代基a中选择的基团；但是当R5是氢原子时，Y不是单键或直链的C1-C10烷基基团。