(Z)-5-phenyl-2,3-dipropyl-1-(p-tolyl)pent-2-en-4-yn-1-ol | 871731-51-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-5-phenyl-2,3-dipropyl-1-(p-tolyl)pent-2-en-4-yn-1-ol
• 英文别名: (Z)-5-phenyl-2,3-dipropyl-1-p-tolyl-2-penten-4-yn-1-ol；(Z)-3-(phenylethynyl)-2-propyl-1-p-tolylhex-2-en-1-ol；(Z)-1-(4-methylphenyl)-3-(2-phenylethynyl)-2-propylhex-2-en-1-ol
• CAS: 871731-51-0
• 化学式: C₂₄H₂₈O
• 分子量: 332.486
• InChiKey: HTOASTFMMRIECO-LNVKXUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-5-phenyl-2,3-dipropyl-1-(p-tolyl)pent-2-en-4-yn-1-ol 在 gold(III) chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 以92%的产率得到2-benzyl-3,4-dipropyl-5-p-tolylfuran
  参考文献：
  名称：

  （Z）-2-en-4-yn-1-ols的金催化环化：完全取代的二氢呋喃和呋喃的高效合成。

  摘要：

  [反应：见正文]在极温和的反应条件下，金催化的（Z）-烯醇的环化反应提供了一条有效而直接的途径来合成立体定义的（Z）-5-亚烷基-2,5-二氢呋喃和完全取代的呋喃。重要的是，结果表明，氧化步骤和原脱金属步骤都是高度立体选择性的。

  DOI：

  10.1021/ol052160r
• 作为产物：
  描述：

  (Z)-5-phenyl-2,3-dipropyl-2-penten-4-yn-1-al 、 对甲苯基溴化镁 在 水 、 氯化铵 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以83%的产率得到(Z)-5-phenyl-2,3-dipropyl-1-(p-tolyl)pent-2-en-4-yn-1-ol
  参考文献：
  名称：

  Alkynylcyanation of alkynes and dienes catalyzed by nickel

  摘要：

  Alkynyl cyanides are found to add across alkynes and 1,2-dienes in the presence of a catalyst prepared in situ from Ni(cod)(2), xantphos, and BPh3. A range of functionalized conjugated cis-enynes are obtained with high regioselectivity. The addition reaction across norbornadiene proceeds in the absence of BPh3 to give exo-cis adduct exclusively. A stoichiometric reaction of ail alkynyl cyanide, Ni(cod)2, xantphos, and BPh3 gives trans-(xantphos)Ni(CNBPh3)(C CSiMe(2)t-Bu), which is suggested to be a plausible reaction intermediate of the alkynylcyanation reaction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.079

文献信息

• Gold-Catalyzed Cyclization of (<i>Z</i>)-2-En-4-yn-1-ols:  Highly Efficient Synthesis of Fully Substituted Dihydrofurans and Furans
  作者：Yuanhong Liu、Feijie Song、Zhiquan Song、Meina Liu、Bin Yan

  DOI：10.1021/ol052160r

  日期：2005.11.1

  [reaction: see text] The gold-catalyzed cyclization of (Z)-enynols offers an efficient and straightforward route to stereodefined (Z)-5-ylidene-2,5-dihydrofurans and fully substituted furans under extremely mild reaction conditions. Importantly, the results indicated that both the oxyauration and the proto-demetalation steps are highly stereoselective.

  [反应：见正文]在极温和的反应条件下，金催化的（Z）-烯醇的环化反应提供了一条有效而直接的途径来合成立体定义的（Z）-5-亚烷基-2,5-二氢呋喃和完全取代的呋喃。重要的是，结果表明，氧化步骤和原脱金属步骤都是高度立体选择性的。
• Nickel/BPh3-Catalyzed Alkynylcyanation of Alkynes and 1,2-Dienes: An Efficient Route to Highly Functionalized Conjugated Enynes
  作者：Yoshiaki Nakao、Yasuhiro Hirata、Masaaki Tanaka、Tamejiro Hiyama

  DOI：10.1002/anie.200704095

  日期：2008.1
• Alkynylcyanation of alkynes and dienes catalyzed by nickel
  作者：Yasuhiro Hirata、Masaaki Tanaka、Akira Yada、Yoshiaki Nakao、Tamejiro Hiyama

  DOI：10.1016/j.tet.2009.03.079

  日期：2009.6

  Alkynyl cyanides are found to add across alkynes and 1,2-dienes in the presence of a catalyst prepared in situ from Ni(cod)(2), xantphos, and BPh3. A range of functionalized conjugated cis-enynes are obtained with high regioselectivity. The addition reaction across norbornadiene proceeds in the absence of BPh3 to give exo-cis adduct exclusively. A stoichiometric reaction of ail alkynyl cyanide, Ni(cod)2, xantphos, and BPh3 gives trans-(xantphos)Ni(CNBPh3)(C CSiMe(2)t-Bu), which is suggested to be a plausible reaction intermediate of the alkynylcyanation reaction. (C) 2009 Elsevier Ltd. All rights reserved.
• A general and efficient synthesis of substituted furans and dihydrofurans via gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols
  作者：Xiangwei Du、Feijie Song、Yuhua Lu、Haoyi Chen、Yuanhong Liu

  DOI：10.1016/j.tet.2008.11.109

  日期：2009.2

  A highly efficient Au-catalyzed cyclization of (Z)-enynols that proceeds under mild reaction conditions has been developed. This methodology provides rapid access to substituted furans and stereodefined (Z)-5-ylidene-2,5-dihydrofurans in a regioselective manner from suitably substituted (Z)-2-en-4-yn-1-ols.

  已经开发了在温和的反应条件下进行的高效Au催化（Z）-烯醇的环化反应。该方法学提供了从适当取代的（Z）-2-en-4-yn-1-ols上以区域选择性方式快速获得取代的呋喃和立体定义的（Z）-5-亚烷基-2,5-二氢呋喃的方法。