2-(4-Chlorobutyl)-1,3-dithiane | 15077-15-3

• 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-(4-Chlorobutyl)-1,3-dithiane
• CAS: 15077-15-3
• 化学式: C₈H₁₅ClS₂
• 分子量: 210.792
• InChiKey: VGSQQLWJVJZWAD-UHFFFAOYSA-N

物化性质

• 沸点：
  311.0±22.0 °C(predicted)
• 密度：
  1.124±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,4,5,6-四氢-3-吡啶甲腈 、 2-(4-Chlorobutyl)-1,3-dithiane 在 potassium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到3-cyano-1-<4-(1,3-dithian-2-yl)butyl>-1,4,5,6-tetrahydropyridine
  参考文献：
  名称：

  3-Cyano-1-[4-(1,3-dithian-2-yl)butyl]-1,4,5,6-tetrahydropyridine

  摘要：

  The title nitrile {1-[4-(1,3-dithian-2-yl)butyl]-1,4,5,6-tetrahydropyridine-3-carbonitrile, C14H22N2S2} was prepared as part of our investigations into the conjugate addition reactions of unsaturated nitriles [Fleming & Pak (1995). J. Org. Chem. 60, 4299-4301]. The tetrahydropyridine ring adopts a half-chair conformation and is appended by a four-carbon chain to the dithiane ring which adopts a chair conformation.

  DOI：

  10.1107/s010827019501345x
• 作为产物：
  描述：

  1,3-二噻烷 、 1-溴-4-氯丁烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以82%的产率得到2-(4-Chlorobutyl)-1,3-dithiane
  参考文献：
  名称：

  Tumor-Targeted Boranes. 4. Synthesis of Nitroimidazole-Carboranes with Polyether-Isoxazole Links

  摘要：

  Carboranes targeted to specific tumor tissues are important for boron neutron capture therapy (BNCT) of cancer. Previous attempts to use isoxazolylphenyl-linked nitroimidazole-carboranes for targeting to hypoxic tumors were hampered by the low polarity and very low aqueous solubility of the compounds. Syntheses of polyether-linked nitroimidazole-isoxazole-carborane 17, 25, and 26 via 1,3-dipolar cycloaddition of appropriate nitroimidazole-alkynes with nitrile oxides derived from aliphatic aldehyde oximes linked by a varying number of water-solubilizing ether units to carborane have been developed. The stabilities of the nitrile oxides were much less than that of the corresponding 4-(carboranylmethoxy)phenyl nitrile oxide and depended on their structure. The yields of isoxazoles varied accordingly and cycloaddition failed when eight ether units were included in the chain. Compounds 17, 25, and 26, with four, five, and six ether units, respectively, had increasingly convenient physical properties to permit biological evaluation.

  DOI：

  10.1021/jo00102a026

文献信息

• α,β-Unsaturated Nitriles:  Stereoselective Conjugate Addition Reactions
  作者：Fraser F. Fleming、Zahid Hussain、Douglas Weaver、Richard E. Norman

  DOI：10.1021/jo9619894

  日期：1997.3.1

  Dithiane anions undergo intramolecular conjugate additions with alpha,beta-unsaturated nitriles when a dithiane anion is tethered to N-1 of the 3-cyano-1,4,5,6-tetrahydropyridine nucleus. 3-Cyano-1-[2-(1,3-dithianyl-2-yl)ethyl]-1,4,5,6-tetrahydropyridine (1a) and the one-carbon homologue 1b cyclize in the presence of 12-crown-4 to generate indolizidine 3 and quinolizidine 9, in which the nitrile group exhibits a strong, thermodynamic preference for the axial orientation. Oxidation of Ib provides dithiane S-oxide 10 that undergoes a highly stereoselective conjugate addition to provide crystalline quinolizidine 13. The X-ray structure of 13 is reported and corroborates our ''peg-in-a-pocket'' principle for stereoselective conjugate additions with alpha,beta-unsaturated nitriles.