(R)-methyl 2-[(1,3-benzothiazol-2-yl)sulfanyl]-2-phenylpropionate | 857665-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (R)-methyl 2-[(1,3-benzothiazol-2-yl)sulfanyl]-2-phenylpropionate
• 英文别名: methyl (2R)-2-(1,3-benzothiazol-2-ylsulfanyl)-2-phenylpropanoate
• CAS: 857665-71-5
• 化学式: C₁₇H₁₅NO₂S₂
• 分子量: 329.444
• InChiKey: RCQXPGPXEOKWFL-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-[(1,3-benzothiazol-2-yl)sulfanyl]-2-phenylpropionate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以95%的产率得到(R)-2-phenyl-2-sulfanyl-1-propanol
  参考文献：
  名称：

  Preparation oftert-Alkyl Aryl Sulfides fromtert-Alcohols via Quinone-mediated Oxidation–Reduction Condensation betweentert-Alkyl Diphenylphosphinites and 2-Sulfanyl-1,3-benzothiazole

  摘要：

  建立了一种从涉及手性叔醇的叔醇出发，构建含硫季碳中心的方便两步法。叔烷基二苯膦亚基1可通过叔醇与ClPPh2在Et3N和催化量DMAP的共同作用下，轻松制备并获得极佳产率。随后，在醌2d的存在下，1与硫醇3的缩合反应顺利进行，通过SN2取代反应以良好至高产率得到相应的叔烷基硫醚4。使用LiAlH4去除(R)-4j的苯并噻唑-2-基团，以高产率得到了所需的手性硫醇(R)-5。

  DOI：

  10.1246/cl.2005.638
• 作为产物：
  描述：

  (S)-methyl atrolactate 在 4-二甲氨基吡啶 、 2,6-二叔丁基苯醌 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 14.0h， 生成 (R)-methyl 2-[(1,3-benzothiazol-2-yl)sulfanyl]-2-phenylpropionate
  参考文献：
  名称：

  Preparation oftert-Alkyl Aryl Sulfides fromtert-Alcohols via Quinone-mediated Oxidation–Reduction Condensation betweentert-Alkyl Diphenylphosphinites and 2-Sulfanyl-1,3-benzothiazole

  摘要：

  建立了一种从涉及手性叔醇的叔醇出发，构建含硫季碳中心的方便两步法。叔烷基二苯膦亚基1可通过叔醇与ClPPh2在Et3N和催化量DMAP的共同作用下，轻松制备并获得极佳产率。随后，在醌2d的存在下，1与硫醇3的缩合反应顺利进行，通过SN2取代反应以良好至高产率得到相应的叔烷基硫醚4。使用LiAlH4去除(R)-4j的苯并噻唑-2-基团，以高产率得到了所需的手性硫醇(R)-5。

  DOI：

  10.1246/cl.2005.638

文献信息

• Stereospecific C–S Bond Formation from Chiral Tertiary Alcohols by Quinone-Mediated Oxidation–Reduction Condensation Using Alkyl Diphenylphosphinites and Its Application to the Synthesis of a Chiral Tertiary Thiol
  作者：Kazuhiro Ikegai、Wanchai Pluempanupat、Teruaki Mukaiyama

  DOI：10.1246/bcsj.79.780

  日期：2006.5

  Oxidation–reduction condensation between 2-sulfanyl-1,3-benzothiazole (Btz-SH) and the alkyl diphenylphosphinites 1, prepared from tertiary alcohols, proceeded smoothly in the presence of 2,6-di-t-...

  2-硫烷基-1,3-苯并噻唑 (Btz-SH) 与由叔醇制备的烷基二苯基亚膦酸酯 1 之间的氧化还原缩合反应在 2,6-di-t-...
• Stereospecific Synthesis of Alkyl Aryl Sulfides from Alcohols and 2-Sulfanylbenzothiazole Using Aryl Diphenylphosphinite and Azide Compounds by a New Type of Oxidation–Reduction Condensation
  作者：Kiichi Kuroda、Yuji Maruyama、Yujiro Hayashi、Teruaki Mukaiyama

  DOI：10.1246/cl.2008.836

  日期：2008.8.5

  The preparation of alkyl aryl sulfides from alcohols and 2-sulfanylbenzothiazole using phenyl diphenylphosphinite and azide compounds by a new type of oxidation–reduction condensation is described....

  描述了使用苯基二苯基次膦酸盐和叠氮化合物通过新型氧化还原缩合反应从醇和 2-硫烷基苯并噻唑制备烷基芳基硫化物。
• A New Type of Oxidation-Reduction Condensation by the Combined Use of Phenyl Diphenylphosphinite and Oxidant
  作者：Teruaki Mukaiyama、Kiichi Kuroda、Yuji Maruyama

  DOI：10.3987/rev-09-sr(s)1

  日期：——

  A new type of oxidation-reduction condensation of alcohols with sulfur, nitrogen, and oxygen nucleophiles by the combined use of phenyl diphenylphosphinite (PhOPPh2) and oxidants such as azides or diethyl azodicarboxylate (DEAD) are described. In these reactions, chiral secondary and tertiary alcohols are converted into the corresponding chiral sulfides, azides, esters and ethers under mild and neutral conditions with almost complete inversion of stereochemical configuration.
• Preparation of<i>tert</i>-Alkyl Aryl Sulfides from<i>tert</i>-Alcohols via Quinone-mediated Oxidation–Reduction Condensation between<i>tert</i>-Alkyl Diphenylphosphinites and 2-Sulfanyl-1,3-benzothiazole
  作者：Kazuhiro Ikegai、Wanchai Pluempanupat、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.638

  日期：2005.5

  A convenient two-step procedure for the construction of sulfur-containing quaternary centers from tert-alcohols involving chiral ones is established. tert-Alkyl diphenylphosphinites 1 were easily prepared in excellent yields from tert-alcohols and ClPPh2 by the combined use of Et3N and a catalytic amount of DMAP. Subsequent condensation of 1 with thiol 3 smoothly proceeded in the presence of quinone 2d to afford the corresponding tert-alkyl sulfides 4 in good to high yields via SN2 displacement. Removal of benzothiazol-2-yl group of (R)-4j was achieved with LiAlH4 to afford the desired chiral thiol (R)-5 in high yield.

  建立了一种从涉及手性叔醇的叔醇出发，构建含硫季碳中心的方便两步法。叔烷基二苯膦亚基1可通过叔醇与ClPPh2在Et3N和催化量DMAP的共同作用下，轻松制备并获得极佳产率。随后，在醌2d的存在下，1与硫醇3的缩合反应顺利进行，通过SN2取代反应以良好至高产率得到相应的叔烷基硫醚4。使用LiAlH4去除(R)-4j的苯并噻唑-2-基团，以高产率得到了所需的手性硫醇(R)-5。
• Conversion of Alcohols to Alkyl Aryl Sulfides by a New Type of Oxidation–Reduction Condensation Using Phenyl Diphenylphosphinite
  作者：Kiichi Kuroda、Yuji Maruyama、Yujiro Hayashi、Teruaki Mukaiyama

  DOI：10.1246/bcsj.82.381

  日期：2009.3.15

  Preparation of alkyl aryl sulfides from alcohols and arenethiols such as 2-sulfanyl-1,3-benzothiazole (BtzSH) is described by a new type of oxidation–reduction condensation using phenyl diphenylpho...

  从醇和芳烃硫醇如 2-硫烷基-1,3-苯并噻唑 (BtzSH) 制备烷基芳基硫化物是通过使用苯基二苯基膦的一种新型氧化还原缩合反应来描述的。