10,15-dihydrotribenzo<1,6>dithiecin | 22887-76-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 10,15-dihydrotribenzo<1,6>dithiecin
• 英文别名: Tribenzodithiecin；1,10-Dithia-<2.2.0>orthocyclophan；8,17-Dithiatetracyclo[16.4.0.02,7.010,15]docosa-1(22),2,4,6,10,12,14,18,20-nonaene
• CAS: 22887-76-9
• 化学式: C₂₀H₁₆S₂
• 分子量: 320.479
• InChiKey: VBSVQWFWIRSWGP-UHFFFAOYSA-N

物化性质

• 熔点：
  100-102 °C
• 沸点：
  527.4±40.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  10,15-dihydrotribenzo<1,6>dithiecin 在 silver tetrafluoroborate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 2,2'-bis(methylthio)-1,1'-biphenyl
  参考文献：
  名称：

  Synthesis and Properties of Novel Medium-sized Heterocyclic Compounds Containing Two Sulfur Atoms in the Ring and Synthetic Approaches to Conjugated Cyclic Disulfonium Ylides

  摘要：

  Tribenzo[b,f,h][1,4]dithiecin (8) was prepared by coupling 2,2'-bis(bromomethyl)biphenyl (10) with 1,2-benzenedithiol (11) in the presence of NaH in acetonitrile. Another novel dithiecin derivative, 1,8-dihydro-2,7-benzodithiecin (9) was synthesized by coupling of 1,4-dimercapto-2,3-O-isopropylidene-Lg-threitol (13a) with alpha,alpha'-dibromo-o-xylene (12), followed by hydrolysis and subsequent dehydration via the mesylate derivative (16). The benzodithiecin (9) was also prepared by treatment of dithiol (18) with butadiyne along with alpha,alpha'-bis(1-buten-3-ynylthio)-o-xylene (19) as a byproduct. Compound (19) was subjected to an intramolecular coupling reaction using CuCl-pyridine-O-2 in benzene to yield the 12-membered ring compound (23). We also describe our effort to prepare the corresponding cyclic diylide compounds from the above new dithiecins (8) and (9), and known dithiecin (7).

  DOI：

  10.3987/com-99-s(i)5
• 作为产物：
  描述：

  2,2'-dimercaptobiphenyl 、 1,2-二(溴甲基)苯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以67%的产率得到10,15-dihydrotribenzo<1,6>dithiecin
  参考文献：
  名称：

  联芳基二硫醇衍生的二硫代环烷的合成与结构表征

  摘要：

  已经研究了二溴化物与联苯-2,2'-二硫醇和1,1'-联萘-2,2'-二硫醇反应生成二噻唑烷的反应的相对效率，这是手性联芳基二硫醇的潜在途径。可拆分的二溴化物2,2'-双（溴甲基）-1,1'-联萘与1,1'-联萘-2,2'-二硫醇的反应得到了二硫代环庚烷的非对映异构体混合物。1,1'-联萘-2,2'-双（亚甲基硫醇）与2,2'-双（溴甲基）-1,1'-联萘的反应生成的混合物包括萘甲酚[2,1-c：1'， 2'-d] thiepin和11,13,26,28-四氢四萘并[2,1-c：1'，2'-e：2“，1” -j：1‴，2‴-l的外消旋非对映异构体] [1,8]二硫代环十四烷。

  DOI：

  10.1016/0040-4020(94)00951-p

文献信息

• Synthesis and structural characterization of dithiacyclophanes derived from biaryldithiols
  作者：Upul K. Bandarage、Lyall R. Hanton、Robin A.J. Smith

  DOI：10.1016/0040-4020(94)00951-p

  日期：1995.1

  1′-binaphthalene-2,2′-bis(methylenethiol) with 2,2′-bis(bromomethyl)-1,1′-binaphthalene gave a mixture including dinaphtho[2,1-c:1′,2′-d]thiepin and the racemic diastereoisomer of 11,13,26,28-tetrahydrotetranaphtho[2,1-c:1′,2′-e:2″,1″-j:1‴,2‴-l][1,8]dithiacyclotetradecin.

  已经研究了二溴化物与联苯-2,2'-二硫醇和1,1'-联萘-2,2'-二硫醇反应生成二噻唑烷的反应的相对效率，这是手性联芳基二硫醇的潜在途径。可拆分的二溴化物2,2'-双（溴甲基）-1,1'-联萘与1,1'-联萘-2,2'-二硫醇的反应得到了二硫代环庚烷的非对映异构体混合物。1,1'-联萘-2,2'-双（亚甲基硫醇）与2,2'-双（溴甲基）-1,1'-联萘的反应生成的混合物包括萘甲酚[2,1-c：1'， 2'-d] thiepin和11,13,26,28-四氢四萘并[2,1-c：1'，2'-e：2“，1” -j：1‴，2‴-l的外消旋非对映异构体] [1,8]二硫代环十四烷。
• Synthesis and Properties of Novel Medium-sized Heterocyclic Compounds Containing Two Sulfur Atoms in the Ring and Synthetic Approaches to Conjugated Cyclic Disulfonium Ylides
  作者：Hiroshi Shimizu、Hiroyoshi Watanabe、Masahiro Mizuno、Tadashi Kataoka、Mikio Hori

  DOI：10.3987/com-99-s(i)5

  日期：——

  Tribenzo[b,f,h][1,4]dithiecin (8) was prepared by coupling 2,2'-bis(bromomethyl)biphenyl (10) with 1,2-benzenedithiol (11) in the presence of NaH in acetonitrile. Another novel dithiecin derivative, 1,8-dihydro-2,7-benzodithiecin (9) was synthesized by coupling of 1,4-dimercapto-2,3-O-isopropylidene-Lg-threitol (13a) with alpha,alpha'-dibromo-o-xylene (12), followed by hydrolysis and subsequent dehydration via the mesylate derivative (16). The benzodithiecin (9) was also prepared by treatment of dithiol (18) with butadiyne along with alpha,alpha'-bis(1-buten-3-ynylthio)-o-xylene (19) as a byproduct. Compound (19) was subjected to an intramolecular coupling reaction using CuCl-pyridine-O-2 in benzene to yield the 12-membered ring compound (23). We also describe our effort to prepare the corresponding cyclic diylide compounds from the above new dithiecins (8) and (9), and known dithiecin (7).