(E)-1-phenylhex-4-en-1-yn-3-ol | 63124-67-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-phenylhex-4-en-1-yn-3-ol
• 英文别名: 1-phenyl-hex-4-en-1-yn-3-ol；(+/-)-1-phenyl-hex-4t-en-1-yn-3-ol；(+/-)-1-Phenyl-hex-4t-en-1-in-3-ol
• CAS: 63124-67-4
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: AXXBQSSDCUHSJH-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (E)-1-phenylhex-4-en-1-yn-3-ol 在 1,4-二氧六环 、 硫酸 作用下， 生成 6-phenyl-hexa-1,3-dien-5-yne
  参考文献：
  名称：

  Okajima, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 1288,1289

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙炔 在 乙醚 、 乙基溴化镁 作用下， 生成 (E)-1-phenylhex-4-en-1-yn-3-ol
  参考文献：
  名称：

  Parker et al., Journal of the Chemical Society, 1958, p. 3871,3873

  摘要：

  DOI：

文献信息

• Chiral Macrocycle-Catalyzed Highly Enantioselective Phenylacetylene Addition to Aliphatic and Vinyl Aldehydes
  作者：Zi-Bo Li、Tian-Dong Liu、Lin Pu

  DOI：10.1021/jo070091j

  日期：2007.6.1

  The 1,1‘-binaphthyl macrocycle (S)-2 is found to be an excellent catalyst for the alkyne addition to aldehydes. In the presence of (S)-2 (20 mol %) and Me2Zn (2 equiv) in THF at room temperature, the addition of phenylacetylene to linear or branched aliphatic aldehydes and vinyl aldehydes gave various propargylic alcohols with 89−96% ee.

  发现1,1'-联萘大环（S）-2是炔烃加成醛的极佳催化剂。在室温下，在THF中存在（S）-2（20 mol％）和Me 2 Zn（2当量）的情况下，将苯乙炔添加到直链或支链脂族醛和乙烯基醛中，制得89-96％的各种炔丙醇ee。
• Silica gel-mediated rearrangement of allylic acetates. Application to the synthesis of 1,3-enynes
  作者：Anna Serra-Muns、Amandine Guérinot、Sébastien Reymond、Janine Cossy

  DOI：10.1039/c0cc00035c

  日期：——

  Silica gel was found to efficiently promote the rearrangement of allylic acetates into their most stable regioisomers under microwave irradiation. The reaction is easy to perform and eco-friendly. This method was applied to the metal-free synthesis of 1,3-enynes.

  发现硅胶在微波辐射下可有效促进乙酸烯丙酯重排成其最稳定的区域异构体。该反应易于进行且对环境友好。该方法用于1，3-烯炔的无金属合成。
• Gold-Catalyzed Tandem Cycloisomerization of Alkynyloxiranes with Nucleophiles: An Efficient Approach to 2,5-Disubstituted Furans
  作者：Xing-Zhong Shu、Xue-Yuan Liu、Hui-Quan Xiao、Ke-Gong Ji、Li-Na Guo、Chen-Ze Qi、Yong-Min Liang

  DOI：10.1002/adsc.200700319

  日期：2007.11.5

  An efficient approach to 2,5-disubstituted furans has been developed by utilizing gold-catalyzed sequential nucleophilic attack onto metal-complexed alkynes with complete regioselectivity. The reaction proceeds efficiently under mild conditions with commercially available catalysts to afford furans in moderate to excellent yields (up to 96 %) with high diversity.

  通过利用金催化的连续亲核攻击具有完全区域选择性的金属络合炔烃，已经开发了一种有效的2,5-二取代呋喃方法。该反应在温和的条件下使用可商购的催化剂有效地进行，从而以中等至优异的收率（高达96％）提供呋喃，并具有很高的多样性。
• Highly Enantioselective Phenylacetylene Additions to Both Aliphatic and Aromatic Aldehydes
  作者：Ge Gao、David Moore、Ru-Gang Xie、Lin Pu

  DOI：10.1021/ol026921r

  日期：2002.11.1

  The readily available and inexpensive BINOL in combination with Ti(O(i)Pr)(4) is found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes including aliphatic aldehydes, aromatic aldehydes, and other alpha,beta-unsaturated aldehydes to generate chiral propargyl alcohols with 91-99% ee at room temperature. No previous chiral catalysts have exhibited such a broad scope

  发现容易获得且便宜的BINOL与Ti（O（i）Pr）（4）结合可催化炔基锌试剂与各种类型的醛反应，包括脂肪族醛，芳族醛和其他α，β-不饱和醛在室温下生成具有91-99％ee的手性炔丙醇。相对于用于该反应的醛的类型，以前的手性催化剂没有表现出如此宽的对映选择性范围。[反应：看文字]
• Double Gold-Catalysed Annulation of Indoles by Enynones
  作者：Stephen J. Heffernan、James P. Tellam、Marine E. Queru、Andrew C. Silvanus、David Benito、Mary F. Mahon、Alan J. Hennessy、Benjamin I. Andrews、David R. Carbery

  DOI：10.1002/adsc.201300018

  日期：2013.4.15

  The gold‐catalysed double functionalisation of indoles is presented. Enynones are used to annulate indoles via a double sodium tetrachloroaurate‐catalysed process involving a mixture of CH activation and alkyne activation modes of promotion. Good yields for the formation of medicinally relevant [6,5,7]‐tricyclic indoles are realised.

  介绍了金催化的吲哚双官能化。Enynones用于有环的吲哚通过涉及℃的混合物中的双钠四氯催化过程 ħ激活和促进炔激活模式。实现了与医学相关的[6,5,7]-三环吲哚的良好生成。