N-cinnamoyl-4S-isopropyl-5,5-dimethyloxazolidinethione | 877377-55-4

• 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: N-cinnamoyl-4S-isopropyl-5,5-dimethyloxazolidinethione
• 英文别名: (E)-1-[(4S)-5,5-dimethyl-4-propan-2-yl-2-sulfanylidene-1,3-oxazolidin-3-yl]-3-phenylprop-2-en-1-one
• CAS: 877377-55-4
• 化学式: C₁₇H₂₁NO₂S
• 分子量: 303.425
• InChiKey: QZDAGYOPWKFHOR-NKSUMMKUSA-N

物化性质

• 沸点：
  385.6±35.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  N-cinnamoyl-4S-isopropyl-5,5-dimethyloxazolidinethione 在 lithium aluminium tetrahydride 、 四氯化锡 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 (4S)-4-异丙基-5,5-二甲基-1,3-恶唑烷-2-酮
  参考文献：
  名称：

  Synthesis of 3-sulfanylpropanols containing three consecutive stereocenters via tandem Michael–aldol reaction of enoylthioamides with acetals as key reaction

  摘要：

  (2S,3S,1'R)-2-(α-甲氧基苯甲基)-3-苯基-3-硫代丙酰胺通过在SnCl4存在下与N-肉桂酰-4S-异丙基-5,5-二甲基硫代氧化二烯的反应有选择性地制备。通过二硫化物的X射线分析确定了三个新形成的连续手性中心的绝对构型。通过还原去除硫代氧化二烯部分将酰胺转化为丙醇。(c) 2005 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.tetlet.2005.08.085
• 作为产物：
  描述：

  (S)-3-氨基-2,4-二甲基戊-2-醇 在 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 生成 N-cinnamoyl-4S-isopropyl-5,5-dimethyloxazolidinethione
  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

• Novel rearrangement of N-enoyl oxazolidinethiones to N-substituted 1,3-thiazine-2,4-diones promoted by NbCl5
  作者：Hector Hernández、Sylvain Bernès、Leticia Quintero、Estibaliz Sansinenea、Aurelio Ortiz

  DOI：10.1016/j.tetlet.2005.12.019

  日期：2006.2

  NbCl5 has been employed as promoter of a novel rearrangement to afford chiral N-substituted 1,3-thiazine-2,4-diones with one or two new stereogenic centers from di- and trisubstituted N-enoyl oxazolidinethiones. The trisubstituted E-isomers provide the anti-diastereomers mainly.

  NbCl 5已被用作新型重排的促进剂，以提供具有一个或两个来自二和三取代的N-烯酰基恶唑烷硫酮的新的立体异构中心的手性N-取代的1,3-噻嗪-2,4-二酮。三取代的E-异构体主要提供抗-非对映异构体。
• (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.
• Synthesis of 3-sulfanylpropanols containing three consecutive stereocenters via tandem Michael–aldol reaction of enoylthioamides with acetals as key reaction
  作者：Hironori Kinoshita、Natsuko Takahashi、Tatsunori Iwamura、Shin-ichi Watanabe、Tadashi Kataoka、Osamu Muraoka、Genzoh Tanabe

  DOI：10.1016/j.tetlet.2005.08.085

  日期：2005.10

  (2S,3S,1'R)-2-(alpha-Methoxybenzyl)-3-phenyl-3-sulfanylpropionamides were diastereoselectively prepared by the reactions of N-cinnamoyl-4S-isopropyl-5,5-dimethyloxazolidinethione with acetals in the presence of SnCl4. The absolute configuration of the three newly created contiguous stereocenters was determined by the X-ray analysis of the disulfide. The amides were transformed into propanols by the reductive removal of the oxazolidinone moiety. (c) 2005 Elsevier Ltd. All rights reserved.

  (2S,3S,1'R)-2-(α-甲氧基苯甲基)-3-苯基-3-硫代丙酰胺通过在SnCl4存在下与N-肉桂酰-4S-异丙基-5,5-二甲基硫代氧化二烯的反应有选择性地制备。通过二硫化物的X射线分析确定了三个新形成的连续手性中心的绝对构型。通过还原去除硫代氧化二烯部分将酰胺转化为丙醇。(c) 2005 Elsevier Ltd. 保留所有权利。