2-(1-hydroxy-1-phenylethyl)-1,3-dithiane | 78349-03-8

• 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-(1-hydroxy-1-phenylethyl)-1,3-dithiane
• 英文别名: 1-(1,3-Dithian-2-yl)-1-phenylethanol
• CAS: 78349-03-8
• 化学式: C₁₂H₁₆OS₂
• 分子量: 240.39
• InChiKey: XOARHCVXTDCGGV-UHFFFAOYSA-N

物化性质

• 沸点：
  396.1±27.0 °C(predicted)
• 密度：
  1.210±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-(1-hydroxy-1-phenylethyl)-1,3-dithiane 在 硫酸 、 水 、 sodium hydride 、 mercury(II) oxide 、 碘甲烷 作用下， 以 四氢呋喃 、 丙酮 、 乙腈 为溶剂， 反应 12.5h， 生成 2-(2-Oxo-propoxy)-2-phenyl-propionaldehyde
  参考文献：
  名称：

  Mercury(II) Chloride-Mediated Cyclization−Rearrangement of O-Propargylglycolaldehyde Dithioacetals to 3-Pyranone Dithioketals:  An Expeditious Access to 3-Pyranones

  摘要：

  O-Propargyl glycolaldehyde dithioacetals undergo a unique cyclization-rearrangement in the presence of mercuric chloride and calcium carbonate to afford 3-pyranones exclusively or along with 2,5-dihydrofuran-3-carboxaldehydes via their dithioketals and dithioacetals.

  DOI：

  10.1021/ol047893a
• 作为产物：
  描述：

  苯乙酮 、 (1,3-dithian-2-yl)triisopropoxytitanium 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 2-(1-hydroxy-1-phenylethyl)-1,3-dithiane
  参考文献：
  名称：

  烷基，芳基和杂取代的有机钛化合物反应中的选择性初步通讯

  摘要：

  标题化合物R-Ti（OR'）3（1）的溶液通常可从等式1的有机锂（或镁）衍生物获得。显示（表1）某些杂取代的有机钛化合物比其锂的热稳定性更高同行。试剂1是高度选择性的亲羰基化合物（表1和2），其反应性可通过改变R'O-基团（表3）和手性（S）-2-甲基-1-丁氧基进行对映选择性修饰。可以实现加法[equ。2]。

  DOI：

  10.1002/hlca.19810640136

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。
• Novel Synthesis of a 1,3,5-Trioxazatriquinane Skeleton Using a Nitrogen Clamp
  作者：Hiroshi Nagase、Akio Watanabe、Masaya Harada、Mayumi Nakajima、Ko Hasebe、Hidenori Mochizuki、Kenji Yoza、Hideaki Fujii

  DOI：10.1021/ol8024988

  日期：2009.2.5

  An α-hydroxyaldehyde derived from naltrexone was converted to an oxazoline dimer with ammonium chloride and sodium acetate in MeOH under reflux. The resulting dimer was treated with dl-camphorsulfonic acid in CHCl3 to give the trimer. The method for trimer synthesis was also applied to general α-hydroxyaldehydes to afford trimers in good yield.

  用氯化铵和乙酸钠在MeOH中的溶液在回流下将衍生自纳曲酮的α-羟醛转化为恶唑啉二聚体。将所得的二聚体在CHCl 3中用dl-樟脑磺酸处理，得到三聚体。三聚体合成的方法也适用于一般的α-羟基醛，以良好的收率得到三聚体。
• An Efficient Photo-SET-Induced Cleavage of Dithiane−Carbonyl Adducts and Its Relevance to the Development of Photoremovable Protecting Groups for Ketones and Aldehydes
  作者：William A. McHale、Andrei G. Kutateladze

  DOI：10.1021/jo981697y

  日期：1998.12.1

  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.
• WEIDMANN B.; MAYCOCK C. D.; SEEBACH D., HELV. CHIM. ACTA, 1981, 64, NO 5, 1552-1557
  作者：WEIDMANN B.、 MAYCOCK C. D.、 SEEBACH D.

  DOI：——

  日期：——
• ANDERSEN, N. H.;MCCRAE, D. A.;GROTJAHN, D. B.;GABHE, S. Y.;THEODORE, L. J+, TETRAHEDRON, 1981, 37, N 23, 4069-4079
  作者：ANDERSEN, N. H.、MCCRAE, D. A.、GROTJAHN, D. B.、GABHE, S. Y.、THEODORE, L. J+

  DOI：——

  日期：——