α,α'-bis(1-buten-3-ynylthio)-o-xylene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α,α'-bis(1-buten-3-ynylthio)-o-xylene
• 英文别名: 1,2-bis[[(Z)-but-1-en-3-ynyl]sulfanylmethyl]benzene
• 化学式: C₁₆H₁₄S₂
• 分子量: 270.419
• InChiKey: LQAQBTPNOKTLCZ-CBIKUMSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  α,α'-bis(1-buten-3-ynylthio)-o-xylene 在 吡啶 、 氧气 、 copper(l) chloride 作用下， 以 苯 为溶剂， 反应 16.0h， 以39.9%的产率得到5,6,7,8-tetrahydro-1,12-dihydro-2,11-benzodithiacyclotetradecin
  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：

  丁二炔 、 1,2-苯二甲硫醇 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以68.7%的产率得到α,α'-bis(1-buten-3-ynylthio)-o-xylene
  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).