2-(dodecylthio)-1-phenylpropan-1-one | 1194360-26-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(dodecylthio)-1-phenylpropan-1-one
• 英文别名: 1-phenyl-2-(dodecylthio)propanone；2-Dodecylsulfanyl-1-phenylpropan-1-one；2-dodecylsulfanyl-1-phenylpropan-1-one
• CAS: 1194360-26-3
• 化学式: C₂₁H₃₄OS
• 分子量: 334.566
• InChiKey: DHCHSXQWGHFRPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(dodecylthio)-1-phenylpropan-1-one 、 苯乙炔 在 H^(1-)*Re⁽¹⁺⁾*4CO={HRe(CO)4} 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以74%的产率得到(Z)-4-(dodecylthio)-2-methyl-1,3-diphenylbut-2-en-1-one
  参考文献：
  名称：

  Terminal催化的端基炔烃插入CS键的区域和立体选择性合成γ-硫代α，β-不饱和酮

  摘要：

  在-催化剂[HRe（CO）4 ] n存在下，α-硫代酮与炔烃的反应以极好的收率得到了γ-硫代-α，β-不饱和酮。炔烃被插入到α-硫酮的碳硫键中，并且双键的异构化为产物提供了高区域选择性和立体选择性。该反应也以分子内方式进行。

  DOI：

  10.1021/ol302810u
• 作为产物：
  描述：

  2-溴苯丙酮 、 十二硫醇 在 sodium hydride 作用下， 以 四氢呋喃 、 oil 为溶剂， 反应 0.5h， 生成 2-(dodecylthio)-1-phenylpropan-1-one
  参考文献：
  名称：

  The effects of C–S and C–Se bonds on torquoselectivity: stereoselective olefination of α-thio and α-selenoketones with ynolates

  摘要：

  Highly Z-selective olefination of acyclic alpha-thio and alpha-selenoketones with ynolates has been achieved, and the theoretical calculations of the transition states in the ring-opening of the intermediates, the beta-lactone enolates, revealed that the torquoselectivity was controlled by the secondary orbital interactions between the sigma orbital of the C-S bond or a lone pair orbital on the S and sigma* orbitals of the breaking C-O bond, and the sigma orbital of the breaking C-O bond or a lone pair orbital on the O on the ring and the sigma* orbitals of the C-S bond. The synthetic applications of the resulting olefins are also shown. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.060

文献信息

• The effects of C–S and C–Se bonds on torquoselectivity: stereoselective olefination of α-thio and α-selenoketones with ynolates
  作者：Takashi Yoshikawa、Seiji Mori、Mitsuru Shindo

  DOI：10.1016/j.tet.2009.08.060

  日期：2009.10

  Highly Z-selective olefination of acyclic alpha-thio and alpha-selenoketones with ynolates has been achieved, and the theoretical calculations of the transition states in the ring-opening of the intermediates, the beta-lactone enolates, revealed that the torquoselectivity was controlled by the secondary orbital interactions between the sigma orbital of the C-S bond or a lone pair orbital on the S and sigma* orbitals of the breaking C-O bond, and the sigma orbital of the breaking C-O bond or a lone pair orbital on the O on the ring and the sigma* orbitals of the C-S bond. The synthetic applications of the resulting olefins are also shown. (c) 2009 Elsevier Ltd. All rights reserved.
• Rhenium-Catalyzed Regio- and Stereoselective Synthesis of γ-Thio-α,β-unsaturated Ketones via Insertion of Terminal Alkynes into the C–S Bond
  作者：Mitsumi Nishi、Yoichiro Kuninobu、Kazuhiko Takai

  DOI：10.1021/ol302810u

  日期：2012.12.7

  α-thioketones and alkynes in the presence of a rhenium catalyst, [HRe(CO)4]n, gave γ-thio-α,β-unsaturated ketones in excellent yields. The alkynes were inserted into the carbon–sulfur bond of the α-thioketones, and isomerization of a double bond provided the products with high regio- and stereoselectivities. This reaction also proceeded in an intramolecular fashion.

  在-催化剂[HRe（CO）4 ] n存在下，α-硫代酮与炔烃的反应以极好的收率得到了γ-硫代-α，β-不饱和酮。炔烃被插入到α-硫酮的碳硫键中，并且双键的异构化为产物提供了高区域选择性和立体选择性。该反应也以分子内方式进行。