(4S,5R)-4-methyl-5-phenyl-3-[(E)-phenylprop-2-enoyl]-1,3-oxazolidine-2-thione | 599164-43-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (4S,5R)-4-methyl-5-phenyl-3-[(E)-phenylprop-2-enoyl]-1,3-oxazolidine-2-thione
• 英文别名: (4S,5R)-3-[(E)-cinnamoyl]-4-methyl-5-phenyl-1,3-oxazolidine-2-thione；(E)-1-[(4S,5R)-4-methyl-5-phenyl-2-sulfanylidene-1,3-oxazolidin-3-yl]-3-phenylprop-2-en-1-one
• CAS: 599164-43-9
• 化学式: C₁₉H₁₇NO₂S
• 分子量: 323.415
• InChiKey: ITSRFYCRBNXLFW-RMCBBKKWSA-N

物化性质

• 熔点：
  82.0-82.5 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  453.7±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-methyl-5-phenyl-3-[(E)-phenylprop-2-enoyl]-1,3-oxazolidine-2-thione 在 盐酸 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 36.5h， 生成 (4S,5R)-(-)-4-甲基-5-苯基-2-恶唑啉酮
  参考文献：
  名称：

  3-肉桂酰基恶唑烷-2-硫酮与醛类之间的不对称串联迈克尔-羟醛反应。

  摘要：

  在BF 3 Et 2 O非对映选择性地存在下，手性3-肉桂酰基-4-甲基-5-苯基-1，3-恶唑烷-2-硫酮与芳族醛之间的反应以高收率选择性地结合了桥键碳与四个杂原子结合的三环化合物。在反应过程中诱导了四个立体中心。通过酸水解，S-甲基化和手性助剂的还原去除，将三环产物转化为带有三个连续立体中心的丙烷-1,3-二醇。

  DOI：

  10.1002/chem.200501435
• 作为产物：
  描述：

  去甲麻黄碱 在 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 生成 (4S,5R)-4-methyl-5-phenyl-3-[(E)-phenylprop-2-enoyl]-1,3-oxazolidine-2-thione
  参考文献：
  名称：

  (S)-4-Isopropyl-5,5-dimethyl-1,3-oxazolidinethione as chiral auxiliary for the intramolecular sulfur transfer in α,β-unsaturated N-acylimides, promoted by NbCl5

  摘要：

  The 1,3-oxazolidinethi one 4 has been synthesized from (S)-valine and used in the intramolecular sulfur transfer in its N-enoyl derivatives in the presence of NbCl5 as catalyst, which, moreover, works as an indicator of the course of the reaction. The adducts have subsequently been transformed into the corresponding beta-mercapto esters by action of Sm(OTf)(3) in methanol. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02837-x

文献信息

• Asymmetric Induction of Three Consecutive Chiral Centers by Reactions of N-Enoylthioamides with Aldehydes
  作者：Tadashi Kataoka、Hironori Kinoshita、Sayaka Kinoshita、Takashi Osamura、Shin-ichi Watanabe、Tatsunori Iwamura、Osamu Muraoka、Genzoh Tanabe

  DOI：10.1002/anie.200351106

  日期：2003.6.30
• (S)-4-Isopropyl-5,5-dimethyl-1,3-oxazolidinethione as chiral auxiliary for the intramolecular sulfur transfer in α,β-unsaturated N-acylimides, promoted by NbCl5
  作者：Aurelio Ortiz、Leticia Quintero、Hector Hernández、Sotero Maldonado、Guadalupe Mendoza、Sylvain Bernès

  DOI：10.1016/s0040-4039(02)02837-x

  日期：2003.2

  The 1,3-oxazolidinethi one 4 has been synthesized from (S)-valine and used in the intramolecular sulfur transfer in its N-enoyl derivatives in the presence of NbCl5 as catalyst, which, moreover, works as an indicator of the course of the reaction. The adducts have subsequently been transformed into the corresponding beta-mercapto esters by action of Sm(OTf)(3) in methanol. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Asymmetric Tandem Michael-Aldol Reactions between 3-Cinnamoyloxazolidine-2-thiones and Aldehydes
  作者：Hironori Kinoshita、Takashi Osamura、Kazumi Mizuno、Sayaka Kinoshita、Tatsunori Iwamura、Shin-ichi Watanabe、Tadashi Kataoka、Osamu Muraoka、Genzoh Tanabe

  DOI：10.1002/chem.200501435

  日期：2006.5.3

  Reactions between chiral 3-cinnamoyl-4-methyl-5-phenyl-1,3-oxazolidine-2-thiones and aromatic aldehydes in the presence of BF3Et2O diastereoselectively produced tricyclic compounds incorporating a bridgehead carbon bound to four heteroatoms in high yields. Four stereocenters were induced during the reaction. The tricyclic products were transformed into propane-1,3-diols bearing three consecutive stereocenters

  在BF 3 Et 2 O非对映选择性地存在下，手性3-肉桂酰基-4-甲基-5-苯基-1，3-恶唑烷-2-硫酮与芳族醛之间的反应以高收率选择性地结合了桥键碳与四个杂原子结合的三环化合物。在反应过程中诱导了四个立体中心。通过酸水解，S-甲基化和手性助剂的还原去除，将三环产物转化为带有三个连续立体中心的丙烷-1,3-二醇。