2-nonyn-4-ol | 106756-97-2

• 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: 2-nonyn-4-ol
• 英文别名: non-2-yn-4-ol；Nonin-(2)-ol-(4)
• CAS: 106756-97-2
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: ZUBAVYJXVVEESR-UHFFFAOYSA-N

物化性质

• 沸点：
  166.3±8.0 °C(Predicted)
• 密度：
  0.885±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  2-nonyn-4-ol 在 六甲基磷酰三胺 、 lithium 作用下， 以 乙醚 为溶剂， 生成 1-nonyn-4-ol
  参考文献：
  名称：

  Larcheveque,M., Bulletin de la Societe Chimique de France, 1968, p. 3387 - 3394

  摘要：

  DOI：
• 作为产物：
  描述：

  1-丙炔溴化镁 、 正己醛 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 2-nonyn-4-ol
  参考文献：
  名称：

  Electrophilic Fluorodesilylation of Allenylmethylsilanes:  A Novel Entry to 2-Fluoro-1,3-dienes

  摘要：

  Various fluorodienes were prepared by treatment of the corresponding allenylmethylsilanes with Selectfluor. This is the first route to these compounds not based on the use of a fluorinated building block. The reaction allows the preparation of 2-fluoro-1,3-dienes with several substitution patterns, including di- and trisubstituted compounds.

  DOI：

  10.1021/ol047319z

文献信息

• Rhodium(I)-Catalyzed Synthesis of Indoles: Amino-Claisen Rearrangement of <i>N</i>-Propargylanilines
  作者：Akio Saito、Shoko Oda、Haruhiko Fukaya、Yuji Hanzawa

  DOI：10.1021/jo8022523

  日期：2009.2.20

  Mild and facile preparations of 2-substituted or 2,3-disubstituted indole compounds were achieved by RhH(CO)(Ph3P)3 (4−10 mol %)-catalyzed reaction of N-propargylanilines in hexafluoroisopropyl alcohol (HFIP). The formation of indoles was proven to be derived from an o-allenylaniline intermediate, which was generated by the Rh(I)-catalyzed amino-Claisen rearrangement of N-propargylanilines. The catalytic

  通过RhH（CO）（Ph 3 P）3（4-10 mol％）催化的N-炔丙基苯胺在六氟异丙醇（HFIP）中的反应，可以实现轻度和简便地制备2-取代或2,3-二取代的吲哚化合物。吲哚的形成被证明源自邻-烯丙基苯胺中间体，其是由R-（I）催化的N-炔丙基苯胺的氨基-克莱森重排产生的。该催化体系也可用于通过在HFIP中在K 2 CO 3（3当量）存在下使N-烷基苯胺（1当量）与炔丙基溴（1.3当量）反应来进行吲哚的一锅合成。活性催化剂被证明是[Rh（CO）（Ph由RhH（CO）（Ph 3 P）3和HFIP原位生成3 P）2 ] OCH（CF 3）2。通过单晶X射线晶体学分析确认了[Rh（CO）（Ph 3 P）2 ] OCH（CF 3）2的结构。
• Regiocontrolled Ruthenium-Catalyzed Isomerization of Propargyl Alcohols
  作者：Edgar Haak、Steffen Skowaisa

  DOI：10.1055/a-2288-3074

  日期：——

  ruthenium complex allows control of regioselectivity in the ruthenium-catalyzed isomerization of propargyl alcohols through the choice of additive. Thereby, both products of the Meyer–Schuster rearrangement and redox isomerization products are selectively accessible. In the presence of hydroxylamine-O-sulfonic acid, unsaturated nitriles are formed instead. The ruthenium catalyst is readily available and

  二氨基环戊二烯酮钌络合物可以通过选择添加剂来控制钌催化的炔丙醇异构化的区域选择性。因此，Meyer-Schuster 重排产物和氧化还原异构化产物都可以选择性地获得。在羟胺-O-磺酸存在下，反而形成不饱和腈。钌催化剂易于获得，并且对水分、空气和酸性条件稳定。
• Tandem Au-Catalyzed 3,3-Rearrangement−[2 + 2] Cycloadditions of Propargylic Esters:  Expeditious Access to Highly Functionalized 2,3-Indoline-Fused Cyclobutanes
  作者：Liming Zhang

  DOI：10.1021/ja056419c

  日期：2005.12.1

  The treatment of readily available propargylic indole-3-acetates with a catalytic amount of AuCl(PPh3)/AgSbF6 leads to tandem activations of the propargylic esters and the in situ generated allenylic esters, resulting in expeditious access to highly functionalized cyclobutanes with fused 2,3-indoline and gamma-lactone rings and an exocyclic E-double bond through sequential 3,3-rearrangement and [2 + 2] cyclization.
• PtCl₂-Catalyzed Rapid Access to Tetracyclic 2,3-Indoline-Fused Cyclopentenes:  Reactivity Divergent from Cationic Au(I) Catalysis and Synthetic Potential
  作者：Guozhu Zhang、Vincent J. Catalano、Liming Zhang

  DOI：10.1021/ja074536x

  日期：2007.9.1

  A PtCl2-catalyzed 3,3-rearrangement/[3+2]-cycloaddition of propargylic 3-indoleacetates is developed. Besides the efficient formation of highly functionalized tetracyclic cyclopentenes, the reaction is dramatically divergent from that catalyzed by cationic Au-I. Moreover, the synthetic potential of this method is demonstrated by a succinct synthesis of the tetracyclic core of vindolinine.
• Autotandem Catalysis with Ruthenium: Remote Hydroesterification of Allylic Amides
  作者：Nicolas Armanino、Marc Lafrance、Erick M. Carreira

  DOI：10.1021/ol4034463

  日期：2014.1.17

  A one-pot tandem sequence involving olefin isomerization and hydroesterification has been developed that enables the incorporation of a C-1-unit at the remote terminal position of allylic amides. Key observations suggest that generation of an active ruthenium hydride, formed by addition of acetic acid, allows both processes to take place under mild conditions in an autotandem catalytic, cascading fashion, which is characterized by the use of a single catalytic entity capable of promoting multiple distinct steps without operator intervention.