(5R,6S)-5-(2-Butyl-[1,3]dithian-2-yl)-6-phenyl-6,7-dihydro-5H-indeno[5,6-d][1,3]dioxole | 142144-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (5R,6S)-5-(2-Butyl-[1,3]dithian-2-yl)-6-phenyl-6,7-dihydro-5H-indeno[5,6-d][1,3]dioxole
• CAS: 142144-38-5
• 化学式: C₂₄H₂₈O₂S₂
• 分子量: 412.617
• InChiKey: GADCJUQNNXHMDF-AUSIDOKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 (5R,6S)-5-(2-Butyl-[1,3]dithian-2-yl)-6-phenyl-6,7-dihydro-5H-indeno[5,6-d][1,3]dioxole
  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

• The addition of Organolithiums to Ketenethioacetals: a new cyclopentannulation sequence leading to indanes.
  作者：David C. Harrowven

  DOI：10.1016/s0040-4039(00)78885-x

  日期：1992.5

  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.