1-hepta-1,2-dien-3-ylcyclopentan-1-ol | 114971-18-5

• 分子结构分类: 有机化合物
• 英文名称: 1-hepta-1,2-dien-3-ylcyclopentan-1-ol
• CAS: 114971-18-5
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: IDPQXZBIAPLRAH-UHFFFAOYSA-N

物化性质

• 沸点：
  261.8±10.0 °C(Predicted)
• 密度：
  0.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-hepta-1,2-dien-3-ylcyclopentan-1-ol 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 乙腈 为溶剂， 生成 2-(1-Bromoethenyl)-2-butylcyclohexan-1-one
  参考文献：
  名称：

  Two-step allylic carbon insertion between ketone carbonyl and α carbons giving α-quaternary α-vinyl ketones

  摘要：

  Ketones 1 were converted to of-quaternary of-vinyl ketones 2 by a two-step formal allylic carbon insertion between ketone carbonyl and alpha carbons, which involves the reaction of 1 with propargyltitanium reagents, derived from propargyl carbonates 3 and a divalent titanium reagent Ti(O-i-Pr)(4)/2i-PrMgCl, and the following rearrangement of the resulting alpha-allenyl alcohols 4 with NBS. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.068
• 作为产物：
  描述：

  环戊酮 、 Ethyl hept-2-ynyl carbonate 在 titanium(IV) isopropoxide 、 异丙基氯化镁 作用下， 以 乙醚 为溶剂， 反应 3.5h， 生成 1-hepta-1,2-dien-3-ylcyclopentan-1-ol
  参考文献：
  名称：

  Two-step allylic carbon insertion between ketone carbonyl and α carbons giving α-quaternary α-vinyl ketones

  摘要：

  Ketones 1 were converted to of-quaternary of-vinyl ketones 2 by a two-step formal allylic carbon insertion between ketone carbonyl and alpha carbons, which involves the reaction of 1 with propargyltitanium reagents, derived from propargyl carbonates 3 and a divalent titanium reagent Ti(O-i-Pr)(4)/2i-PrMgCl, and the following rearrangement of the resulting alpha-allenyl alcohols 4 with NBS. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.068

文献信息

• Palladium-Catalyzed Reaction of Propargylic Acetates with Carbonyl Compounds by SmI₂
  作者：Takanori Tabuchi、Junji Inanaga、Masaru Yamaguchi

  DOI：10.1246/cl.1987.2275

  日期：1987.11.5

  Reductive addition of propargylic acetates to carbonyl compounds proceeded smoothly at room temperature by using SmI2 and a catalytic amount of Pd(PPh3)4 to give the corresponding acetylenic and/or allenic alcohols with appreciable selectivity. The method is useful especially for the preparation of tri- and tetrasubstituted allenic alcohols.

  使用 SmI2 和一定量的 Pd(PPh3)4，丙炔基乙酸酯与羰基化合物的还原加成反应在室温下顺利进行，并以明显的选择性得到相应的乙炔醇和/或烯醇。该方法尤其适用于制备三取代和四取代的联烯醇。
• Palladium(0)-catalyzed reaction of propargylic phosphates with SmI2: A highly regioselective route to the synthesis of allenes and acetylenes
  作者：Koichi Mikami、Akihiro Yoshida、Shoji Matsumoto、Feng Feng、Youichi Matsumoto、Akihiro Sugino、Takeshi Hanamoto、Junji Inanaga

  DOI：10.1016/0040-4039(94)02357-h

  日期：1995.2

  A highly regioselective reaction of propargylic phosphates has been established by using SmI2 and a Pd(0) catalyst to give allenes and acetylenes in high isolated yields depending on the substrate used.

  通过使用SmI 2和Pd（0）催化剂已建立了炔丙基磷酸酯的高度区域选择性反应，具体取决于所使用的底物，从而以高分离产率得到丙二烯和乙炔。
• Mikami Koichi, Yoshida Akihiro, Matsumoto Shoji, Feng Feng, Matsumoto You+, Tetrahedron Lett, 36 (1995) N 6, S 907-908
  作者：Mikami Koichi, Yoshida Akihiro, Matsumoto Shoji, Feng Feng, Matsumoto You+

  DOI：——

  日期：——