4butyl-1-cyclopentyl-2-octyn-4-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4butyl-1-cyclopentyl-2-octyn-4-ol
• 英文别名: 4-Butyl-1-cyclopentyl-2-octyn-4-ol；5-(3-cyclopentylprop-1-ynyl)nonan-5-ol
• 化学式: C₁₇H₃₀O
• 分子量: 250.425
• InChiKey: SNXVURABODEFHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-环戊基-1-丙炔 在 六甲基磷酰三胺 、 正丁基锂 、 samarium diiodide 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 1.0h， 生成 4butyl-1-cyclopentyl-2-octyn-4-ol
  参考文献：
  名称：

  Generation and Reactions of Alkynylsamariums

  摘要：

  Three methods have been developed for generating alkynylsamariums: (1) reduction of iodoalkynes with SmI2 in the presence of HMPA, (2) deprotonation at the terminal position of 1-alkynes either by tetrahydrofurylsamarium generated by PhI and SmI2 in THF, or, (3) deprotonation by butyllithium followed by metal-metal exchange with SmI3. Alkynylsamariums arising from iodoalkynes with SmI2? undergo coupling with carbonyl compounds under both Barbier and Grignard conditions in benzene-HMPA or THF-HMPA as a solvent system. Tetrahydrofurylsamarium generated from iodobenzene and SmI2 in THF can deprotonate from terminal alkynes to yield alkynylsamariums whereas other alkylsamariums, such as ethyl-, isopropyl, cyclohexyl-, and cyclopentylsamarium do not work well. Metal-metal exchange between an alkynyllithium and SmI3 is also effective; the reactive species in this case would be alkynylsamariums rather than alkynyllithiums. To reveal the properties of alkynylsamariums, we examined the stability and reactivity of alkynylsamariums toward Various electrophiles. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00971-6

文献信息

• SmI2-Mediated coupling reactions between iodoalkynes and ketones or aldehydes to give propargyl alcohols
  作者：Munetaka Kunishima、Shinobu Tanaka、Kazuhiro Kono、Kazuhito Hioki、Shohei Tani

  DOI：10.1016/0040-4039(95)00659-z

  日期：1995.5

  Samarium iodide (SmI2) mediates a coupling reaction between alkynyl iodides and ketones or aldehydes to give propargyl alcohols in the presence of hexamethylphosphoric triamide (HMPA) in either benzene or tetrahydrofuran (THF). An alkynylsamarium is involved as an intermediate.

  碘化mar（SmI 2）可以在六甲基磷酸三酰胺（HMPA）存在下，在苯或四氢呋喃（THF）中介导炔基碘和酮或醛之间的偶联反应，从而生成炔丙醇。炔sa作为中间体。
• Generation and Reactions of Alkynylsamariums
  作者：Munetaka Kunishima、Daisuke Nakata、Shinobu Tanaka、Kazuhito Hioki、Shohei Tani

  DOI：10.1016/s0040-4020(00)00971-6

  日期：2000.12

  Three methods have been developed for generating alkynylsamariums: (1) reduction of iodoalkynes with SmI2 in the presence of HMPA, (2) deprotonation at the terminal position of 1-alkynes either by tetrahydrofurylsamarium generated by PhI and SmI2 in THF, or, (3) deprotonation by butyllithium followed by metal-metal exchange with SmI3. Alkynylsamariums arising from iodoalkynes with SmI2? undergo coupling with carbonyl compounds under both Barbier and Grignard conditions in benzene-HMPA or THF-HMPA as a solvent system. Tetrahydrofurylsamarium generated from iodobenzene and SmI2 in THF can deprotonate from terminal alkynes to yield alkynylsamariums whereas other alkylsamariums, such as ethyl-, isopropyl, cyclohexyl-, and cyclopentylsamarium do not work well. Metal-metal exchange between an alkynyllithium and SmI3 is also effective; the reactive species in this case would be alkynylsamariums rather than alkynyllithiums. To reveal the properties of alkynylsamariums, we examined the stability and reactivity of alkynylsamariums toward Various electrophiles. (C) 2000 Elsevier Science Ltd. All rights reserved.