trans-3-(2-butyl-1,3-dithian-2-yl)-2,3-dihydro-2,2-dimethyl-1H-inden-1-ol | 142144-33-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: trans-3-(2-butyl-1,3-dithian-2-yl)-2,3-dihydro-2,2-dimethyl-1H-inden-1-ol
• CAS: 142144-33-0
• 化学式: C₁₉H₂₈OS₂
• 分子量: 336.563
• InChiKey: VJAUYDZDUUOZTL-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-甲基-2-丁烯醛 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 trans-3-(2-butyl-1,3-dithian-2-yl)-2,3-dihydro-2,2-dimethyl-1H-inden-1-ol
  参考文献：
  名称：

  The addition of Organolithiums to Ketenethioacetals: a new cyclopentannulation sequence leading to indanes.

  摘要：

  A new cyclopentannulation sequence leading to the rapid preparation of highly substituted indanes e.g. (3) is described. This novel cyclisation protocol is effected via the initial union of an aryl bromide such as (1) with a 2-lithio-2-vinyl-1,3-dithiane e.g. (2) leading to a ketenethioacetal e.g. (4). Transmetallation to the corresponding aryllithium e.g. (5), by addition of an alkyllithium reagent, next effects an intramolecular 5-exo-trig cyclisation onto the ketenethioacetal moiety, leading to an indane intermediate, e.g. (6). Subsequent in situ alkylation of this intermediate (6), with the alkyl bromide generated as a consequence of transmetallation, then completes the sequence.

  DOI：

  10.1016/s0040-4039(00)78885-x

文献信息

• A triple umpolung sequence for the preparation of highly substituted indanes
  作者：David C. Harrowven、Rory Browne

  DOI：10.1016/0040-4020(96)00907-6

  日期：1996.11

  The paper describes a new method for the diastereoselective construction of highly substituted indanes. The key step involves a triple umpolung sequence in which a 2-lithio-2-vinyl-1,3-dithiane is first united with an aryl halide to form a ketenedithioacetal. Transmetallation of the aryl halide with an alkyllithium reagent then generates an alkyl halide and a 2-indanyl-2-lithio-1,3-dithiane. Finally

  本文介绍了一种用于非对映选择性构建高度取代的茚满的新方法。关键步骤涉及三重酚醛磷酸酯顺序，其中首先将2-lithio-2-乙烯基-1,3-二硫杂环丁烷与芳基卤化物结合形成酮二硫缩醛。然后用烷基锂试剂对芳基卤化物进行金属化反应，生成烷基卤化物和2-茚满基-2-二硫代-1,3-二硫杂环丁烷。最后，这些结合起来以完成序列。