1,2-bis(3-hydroxy-1-propynyl)cyclopentene | 911710-18-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-bis(3-hydroxy-1-propynyl)cyclopentene
• 英文别名: 3-[2-(3-Hydroxyprop-1-ynyl)cyclopenten-1-yl]prop-2-yn-1-ol
• CAS: 911710-18-4
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: HOTGPAZMBIIEOR-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  323.4±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-bis(3-hydroxy-1-propynyl)cyclopentene 、 二苯基氯化膦 、 富马酸二甲酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以64%的产率得到dimethyl trans-4,9-bis(diphenylphosphinyl)-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalene-6,7-dicarboxylate
  参考文献：
  名称：

  Reaction of ene-bis(phosphinylallenes): [2+2] versus [4+2] cycloaddition

  摘要：

  Reaction of ene-bis(phosphinylallenes), derived from ene-bis(propargyl alcohols) and chlorodiphenylphosphine, was investigated. Benzene-bridged bis(phosphinylallenes) exclusively gave intramolecular [2+2] cycloadducts in the presence of dimethyl fumarate in sharp contrast to the reaction of benzene-bridged bis(sulfinylallenes), which gave the corresponding [4+2] cycloadducts. On the other hand, substituted ethylene- or five-membered heterocycle-bridged bis(phosphinylallenes) provided [4+2] cycloadducts. Reaction of benzene-bridged diallene bearing both a sulfinyl group and a phosphinyl group on the two allenyl groups was also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.083
• 作为产物：
  描述：

  tert-Butyl-{3-[2-(2,2-dibromo-vinyl)-cyclopent-1-enyl]-prop-2-ynyloxy}-diphenyl-silane 在 乙基溴化镁 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.58h， 生成 1,2-bis(3-hydroxy-1-propynyl)cyclopentene
  参考文献：
  名称：

  源自烯-双（亚磺酰基烯）的邻-喹啉甲烷的分子间[4 + 2]环加成反应

  摘要：

  研究了由烯-双（炔丙醇）和苯亚磺酰氯通过烯-双（亚磺酰基烯丙基）形成原位制备的邻喹啉甲烷的分子间[4 + 2]环加成反应。苯桥双（炔丙基醇）与缺电子和富电子的烯烃反应，生成相应的[4 + 2]环加合物。乙烯桥联的双（炔丙基醇）与缺电子的烯烃进行类似的环加成反应。还描述了基于新开发的顺序反应构建一些杂环的方法。

  DOI：

  10.1021/jo061014b

文献信息

• Reaction of ene-bis(phosphinylallenes): [2+2] versus [4+2] cycloaddition
  作者：Shinji Kitagaki、Yuki Okumura、Chisato Mukai

  DOI：10.1016/j.tet.2006.08.083

  日期：2006.10

  Reaction of ene-bis(phosphinylallenes), derived from ene-bis(propargyl alcohols) and chlorodiphenylphosphine, was investigated. Benzene-bridged bis(phosphinylallenes) exclusively gave intramolecular [2+2] cycloadducts in the presence of dimethyl fumarate in sharp contrast to the reaction of benzene-bridged bis(sulfinylallenes), which gave the corresponding [4+2] cycloadducts. On the other hand, substituted ethylene- or five-membered heterocycle-bridged bis(phosphinylallenes) provided [4+2] cycloadducts. Reaction of benzene-bridged diallene bearing both a sulfinyl group and a phosphinyl group on the two allenyl groups was also described. (c) 2006 Elsevier Ltd. All rights reserved.
• Intermolecular [4 + 2] Cycloaddition of <i>o</i>-Quinodimethanes Derived from Ene−Bis(sulfinylallenes)
  作者：Shinji Kitagaki、Kumiko Katoh、Kazuhiro Ohdachi、Yuji Takahashi、Daisuke Shibata、Chisato Mukai

  DOI：10.1021/jo061014b

  日期：2006.9.1

  investigated. Benzene-bridged bis(propargyl alcohols) reacted with both electron-deficient and electron-rich olefins to give the corresponding [4 + 2] cycloadducts. Ethylene-bridged bis(propargyl alcohols) underwent similar cycloaddition with electron-deficient olefins. Construction of some heterocycles based on the newly developed sequential reaction is also described.

  研究了由烯-双（炔丙醇）和苯亚磺酰氯通过烯-双（亚磺酰基烯丙基）形成原位制备的邻喹啉甲烷的分子间[4 + 2]环加成反应。苯桥双（炔丙基醇）与缺电子和富电子的烯烃反应，生成相应的[4 + 2]环加合物。乙烯桥联的双（炔丙基醇）与缺电子的烯烃进行类似的环加成反应。还描述了基于新开发的顺序反应构建一些杂环的方法。