2-(2-bromoethyl)-1,3-dithiane | 124764-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 2-(2-bromoethyl)-1,3-dithiane
• CAS: 124764-31-4
• 化学式: C₆H₁₁BrS₂
• 分子量: 227.189
• InChiKey: RUWXEZPPLAHETC-UHFFFAOYSA-N

物化性质

• 沸点：
  95-100 °C(Press: 0.1 Torr)
• 密度：
  1.454±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-bromoethyl)-1,3-dithiane 在 正丁基锂 作用下， 生成 2-[(2R)-2-(1,3-dithian-2-yl)propyl]-2-[2-[2-(2-methylprop-1-enyl)-1,3-dithian-2-yl]ethyl]-1,3-dithiane
  参考文献：
  名称：

  Stereochemical elucidation of the 1,4 polyketide amphidinoketide I

  摘要：

  两栖枝霉酮I的相对和绝对立体化学已通过所有非对映异构体的全合成得以确定。分子建模表明，天然产物并非热力学上优先的非对映异构体。

  DOI：

  10.1039/b309104j
• 作为产物：
  描述：

  2-(1,3-二噻烷-2-基)乙醇 在 四溴化碳 、 三苯基膦 作用下， 生成 2-(2-bromoethyl)-1,3-dithiane
  参考文献：
  名称：

  Stereochemical elucidation of the 1,4 polyketide amphidinoketide I

  摘要：

  两栖枝霉酮I的相对和绝对立体化学已通过所有非对映异构体的全合成得以确定。分子建模表明，天然产物并非热力学上优先的非对映异构体。

  DOI：

  10.1039/b309104j

文献信息

• The Scope and Limitations of 1,3-Stannyl Shift-Promoted Intramolecular Cyclizations of α-Stannyl Radicals with a Formyl Group
  作者：Shau-Hua Ueng、Ming-Jen Chen、Shu-Fang Chu、Yar-Fang Shao、Gang-Ting Fan、Sheng-Yueh Chang、Yeun-Min Tsai

  DOI：10.1021/jo052176v

  日期：2006.2.1

  and serves as a driving force to promote the cyclizations. Although the cyclization rates can be accelerated when the formyl group carries α-dimethyl substituents, unfortunately β-scission of the alkoxy radicals becomes competitive with the 1,3-stannyl shift. The β-stannyloxy radicals can be employed in further cyclizations to obtain tandem cyclization products.

  α-三丁基锡烷基可以由相应的溴化物或黄药生成。这些基团经过带有甲酰基的有效分子内1，5-环化反应。所得的β-锡烷基烷氧基通过从碳到氧的1，3-锡烷基转移进行，以提供β-锡烷基氧基。这种新颖的重排极有可能是不可逆的，并且是促进环化的驱动力。尽管当甲酰基带有α-二甲基取代基时可以加快环化速率，但是不幸的是，烷氧基的β-断裂与1，3-锡烷基移位竞争。可以将β-锡烷基氧基用于进一步的环化以获得串联环化产物。
• Anti-Markovnikov addition to alkenes with a neighbouring thioacetal function
  作者：Tim Bongardt、Sylvia Dreeßen、Ralf Tiedemann、Ernst Schaumann

  DOI：10.1016/j.tetlet.2006.05.009

  日期：2006.7

  The acid-induced cyclisation of unsaturated thioacetals 6 gives anti-Markovnikov products 9, apparently involving sulfur elimination and readdition. (c) 2006 Elsevier Ltd. All rights reserved.
• The Study of the Kinetics of Intramolecular Radical Cyclizations of Acylsilanes via the Intramolecular Competition Method
  作者：Weir-Torn Jiaang、Hsien-Chang Lin、Kuo-Hsiang Tang、Lih-Bin Chang、Yeun-Min Tsai

  DOI：10.1021/jo982079k

  日期：1999.1.1

  The kinetics of the radical cyclizations of acylsilanes is probed by the construction of an intramolecular competition system. In this system, known rate constants of olefin cyclizations are used as the internal clock. At-benzene reflux temperature (80 degrees C), the cyclization rate constants for 5-exo cyclizations of acylsilanes with primary radicals are on the order of 10(6) s(-1). The corresponding rate constants for 5-exo cyclizations with secondary radicals and 6-exo cyclizations with primary radicals lie on the order of 10(5) s(-1). The 6-exo cyclizations of acylsilanes with secondary radicals are slower and fall in the range of 10(4) s(-1). Substituents on the silicon of the acylsilanes affect the rates of cyclization. Large silyl groups reduce the rate, and this is more serious for the g-exo type of cyclizations. Electron-withdrawing groups increase the rates of cyclization.
• A Novel 1,3-Stannyl Shift Promoted Intramolecular Cyclizations of α-Stannyl Radicals with a Formyl Group
  作者：Sheng-Yueh Chang、Yar-Fang Shao、Shu-Fang Chu、Gang-Ting Fan、Yeun-Min Tsai

  DOI：10.1021/ol990199o

  日期：1999.9.1

  [GRAPHICS]Reactions of alpha-stannyl bromides and xanthates with tributyltin hydride generate a stannyl radicals, Intramolecular cyclizations of these radicals with a formyl group afford gamma-stannyl alkoxy radicals that undergo a 1,3-stannyl shift from carbon to oxygen. The carbon radicals obtained can be trapped inter- or intramolecularly. Approximately, the rates of 5-exo cyclizations of alpha-stannyl radicals with a formyl group and terminal olefin are similar.
• DAVEY, ANDREW E.;PARSONS, ANDREW F.;TAYLOR, RICHARD J. K., J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N0, C. 1853-1858
  作者：DAVEY, ANDREW E.、PARSONS, ANDREW F.、TAYLOR, RICHARD J. K.

  DOI：——

  日期：——