(E)-1-(1,3-dithian-2-yl)-3-phenylprop-2-en-1-ol | 75478-63-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-1-(1,3-dithian-2-yl)-3-phenylprop-2-en-1-ol
• 英文别名: trans-1-(1,3-dithian-2-yl)-3-phenyl-2-propenol
• CAS: 75478-63-6
• 化学式: C₁₃H₁₆OS₂
• 分子量: 252.401
• InChiKey: KCHLSCYKZOBDJF-BQYQJAHWSA-N

物化性质

• 沸点：
  443.0±35.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(1,3-dithian-2-yl)-3-phenylprop-2-en-1-ol 在 二苯甲酮 作用下， 以 氘代乙腈 为溶剂， 反应 0.42h， 生成 cis-1-(1,3-dithian-2-yl)-3-phenyl-2-propenol
  参考文献：
  名称：

  An Efficient Photo-SET-Induced Cleavage of Dithiane−Carbonyl Adducts and Its Relevance to the Development of Photoremovable Protecting Groups for Ketones and Aldehydes

  摘要：

  Irradiation of dithiane-aldehyde/ketone adducts in the presence of benzophenone leads to C-C bond cleavage regenerating the carbonyl compounds. It is established that the mechanism of this reaction involves photochemically induced single electron transfer from the dithiane moiety to the excited molecule of ET-photosensitizer, accompanied by mesolytic C-C cleavage in the generated cation-radical, which is assisted by the anion-radical of benzophenone. This mechanism is confirmed by a Hammett plot study of the cleavage in the dithiane adducts of substituted aromatic aldehydes and a deuterium kinetic isotope effect study. Ab initio computations at UHF/6-31G* and MP2/6-31G* levels of theory in conjunction with self-consistent reaction field (self-consistent isodensity-polarized continuum model), to account for the solvent effect, also support the experimental findings. The reaction is most efficient for protection of aromatic aldehydes and ketones and aliphatic ketones, and is a novel method for protecting carbonyl functionalities with a photoremovable group.

  DOI：

  10.1021/jo981697y
• 作为产物：
  描述：

  反式肉桂醛 、 2-lithio-1,3-dithiane 反应 0.5h， 以70%的产率得到(E)-1-(1,3-dithian-2-yl)-3-phenylprop-2-en-1-ol
  参考文献：
  名称：

  1,3-二硫代烷中的1,4-加成锂化衍生物到α-不饱和醛中：制备δ-羰基醛的一种方法

  摘要：

  在THF-HMPA中进行1，4-在α-不饱和醛上的1，3-二硫杂环丁烷和2-苯基-1，3-二硫杂环丁烷的锂化衍生物的加成；该反应可能是制备δ-羰基醛的有趣方法。

  DOI：

  10.1016/s0040-4039(00)78638-2

文献信息

• Lewis Base Catalyzed 1,3-Dithiane Addition to Carbonyl Compounds Using 2-Trimethylsilyl-1,3-dithiane
  作者：Makoto Michida、Teruaki Mukaiyama

  DOI：10.1246/cl.2008.26

  日期：2008.1.5

  1,3-Dithiane addition to various aldehydes and ketones using 2-trimethylsilyl-1,3-dithiane in the presence of a catalytic amount of a Lewis base such as tetrabutylammonium phenoxide (PhONn-Bu4) proceeds smoothly to afford the corresponding α-hydroxy dithiane compounds in good to high yields under mild conditions.

  1,3-二硫烷在存在催化量路易斯碱（如四丁基铵苯氧化物（PhONn-Bu4））的条件下与各种醛和酮的加成反应，使用2-三甲基硅基-1,3-二硫烷，可以顺利进行，得到相应的α-羟基二硫烷化合物，产率良好到高，并且反应条件温和。
• Bu₄N⁺ Alkoxide-Initiated/Autocatalytic Addition Reactions with Organotrimethylsilanes
  作者：Manas Das、Donal F. O’Shea

  DOI：10.1021/jo5007637

  日期：2014.6.20

  The use of Me3SiO(-)/Bu4N(+) as a general activator of organotrimethylsilanes for addition reactions has been established. The broad scope of the method offers trimethylsilanes (including acetate, allyl, propargyl, benzyl, dithiane, heteroaryl, and aryl derivatives) as bench-stable organometallics that can be readily utilized as carbanion equivalents for synthesis. Reactions are achieved at rt without the requirement of specialized precautions that are commonplace for other organometallics.
• EL-BOUZ M.; WARTSKI L., TETRAHEDRON LETT., 1980, 21, NO 30, 2897-2900
  作者：EL-BOUZ M.、 WARTSKI L.

  DOI：——

  日期：——
• WARTSKI, L.;EL, BOUZ, M., TETRAHEDRON, 1982, 38, N 22, 3285-3289
  作者：WARTSKI, L.、EL, BOUZ, M.

  DOI：——

  日期：——
• 1,4-addition of lithiated derivatives from 1,3-dithianes to α-unsaturated aldehydes : A way to δ-carbonyl aldehydes
  作者：Mahmoud El-Bouz、Lya Wartski

  DOI：10.1016/s0040-4039(00)78638-2

  日期：1980.1

  1,4-Addition of the lithiated derivatives of the 1,3-dithiane and 2-phenyl-1,3-dithiane on α-unsaturated aldehydes is performed in THF-HMPA ; this reaction could be an interesting way to δ-carbonyl aldehydes.

  在THF-HMPA中进行1，4-在α-不饱和醛上的1，3-二硫杂环丁烷和2-苯基-1，3-二硫杂环丁烷的锂化衍生物的加成；该反应可能是制备δ-羰基醛的有趣方法。