(4R)-ethyl-4-[2-(thiophen-2-yl)ethenyl]-1,3-oxazolidin-2-one | 921938-01-4

• 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)-ethyl-4-[2-(thiophen-2-yl)ethenyl]-1,3-oxazolidin-2-one
• 英文别名: (4R)-4-Ethyl-4-[2-(thiophen-2-yl)ethenyl]-1,3-oxazolidin-2-one；(4R)-4-ethyl-4-(2-thiophen-2-ylethenyl)-1,3-oxazolidin-2-one
• CAS: 921938-01-4
• 化学式: C₁₁H₁₃NO₂S
• 分子量: 223.296
• InChiKey: XEFZLRAMNCMVHP-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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)-ethyl-4-[2-(thiophen-2-yl)ethenyl]-1,3-oxazolidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 (4R)-ethyl-4-[2-(thiophen-2-yl)ethyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of α,α-disubstituted α-amino alcohol derivatives

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2006.10.007
• 作为产物：
  描述：

  (2-噻吩基甲基)三苯基溴化膦 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 6.83h， 生成 (4R)-ethyl-4-[2-(thiophen-2-yl)ethenyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of α,α-disubstituted α-amino alcohol derivatives

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2006.10.007

文献信息

• 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.