1,3,4,5,6,8-hexahydro-4,5-O-isopropylidene-2,7-benzodithiecin | 332080-78-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,5,6,8-hexahydro-4,5-O-isopropylidene-2,7-benzodithiecin
• 英文别名: (5R,9R)-7,7-dimethyl-6,8-dioxa-3,11-dithiatricyclo[11.4.0.05,9]heptadeca-1(17),13,15-triene
• CAS: 332080-78-1
• 化学式: C₁₅H₂₀O₂S₂
• 分子量: 296.455
• InChiKey: PSFCMNPJCHLOSW-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3,4,5,6,8-hexahydro-4,5-O-isopropylidene-2,7-benzodithiecin 在 DOWEX 50W-X₂ 、 potassium tert-butylate 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 2,7-dimethyl-1,8-dihydro-2,7-benzodithiecin-2,7-diium bis(tetrafluoroborate)
  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：

  2,3-O-isopropylidene-1,4-dithiol-Lg-threitol 、 1,2-二(溴甲基)苯 在 氢氧化钾 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 36.0h， 以77%的产率得到1,3,4,5,6,8-hexahydro-4,5-O-isopropylidene-2,7-benzodithiecin
  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

文献信息

• 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).