4-hydroxy-1,1-diethyl-2-butyn-1-ol | 163005-62-7

• 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: 4-hydroxy-1,1-diethyl-2-butyn-1-ol
• 英文别名: 4-ethyl-hex-2-yne-1,4-diol；4-Aethyl-hex-2-in-1,4-diol；4-ethylhex-2-yn-1,4-diol；4-Ethylhex-2-yne-1,4-diol
• CAS: 163005-62-7
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: OXSALEISXNHGAE-UHFFFAOYSA-N

物化性质

• 沸点：
  139-140 °C(Press: 17 Torr)
• 密度：
  1.0005 g/cm3(Temp: 18 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  4-hydroxy-1,1-diethyl-2-butyn-1-ol 在 镍 作用下， 生成 4-乙基-己烷-1,4-二醇
  参考文献：
  名称：

  Gouge, Annales de Chimie (Cachan, France), 1951, vol. <12> 6, p. 648,682

  摘要：

  DOI：
• 作为产物：
  描述：

  2-丙炔-1-醇 、 3-戊酮 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以55%的产率得到4-hydroxy-1,1-diethyl-2-butyn-1-ol
  参考文献：
  名称：

  A Novel Methodology for the Synthesis of Cyclic Carbonates Based on the Palladium-Catalyzed Cascade Reaction of 4-Methoxycarbonyloxy-2-butyn-1-ols with Phenols, Involving a Novel Carbon Dioxide Elimination-Fixation Process

  摘要：

  A palladium-catalyzed CO2-recycling reaction has been developed. Reaction of 4-methoxycarbonyloxy-2-butyn-1-ols with phenols, carried out in the presence of a palladium catalyst, produces phenoxy-substituted cyclic carbonates by way of a pathway involving a CO2 elimination-fixation. A variety of propargylic alcohols and phenols participate in these reactions which yield cyclic carbonates with high efficiencies. Stereoselective construction of trans-cyclic carbonates is achieved by using nonsymmetric substrates. Highly enantioselective reactions occur when (S)-BINAP is used as a ligand. Reaction of 4-phenoxycarbonyloxy2-butyn-1-ol in the presence of the palladium catalyst yields the corresponding cyclic carbonates via a three-component decomposition-reconstruction process.

  DOI：

  10.1021/ja0340681

文献信息

• Enantioselective Allenation of Terminal Alkynes Catalyzed by Copper Halides of Mixed Oxidation States and Its Application to the Total Synthesis of Scorodonin
  作者：Guolin Wu、Yuan Yao、Gen Li、Xue Zhang、Hui Qian、Shengming Ma

  DOI：10.1002/anie.202112427

  日期：2022.1.21

  of 1,4-diyn-3-yl amine intermediates has been developed. Various allenynes were obtained with excellent enantioselectivities. This reaction was applied to the first highly enantioselective total synthesis of natural product (−)-scorodonin and its enantiomer.

  已经开发了一种高效的 CuCl/CuBr 2共催化 2-炔烃的对映选择性艾伦化反应，涉及 1,4-二炔-3-基胺中间体的高度区域选择性和立体选择性 1,5-H 转移。获得了具有优异对映选择性的各种丙炔。该反应首次应用于天然产物 (-)-scorodin 及其对映异构体的高度对映选择性全合成。
• Vitamin D analogues
  申请人：Leo Pharmaceutical Products Ltd. A/S (L.o slashed.vens Kemiske Fabrik

  公开号：US05716945A1

  公开（公告）日：1998-02-10

  The present invention relates to compounds of formula in which formula X is hydrogen or hydroxy; R.sup.1 and R.sup.2, which may be the same or different, stand for hydrogen or C.sub.1 -C.sub.4 hydrocarbyl; or R.sup.1 and R.sup.2, taken together with the carbon atom bearing the group X, can form a C.sub.3 -C.sub.8 carbocyclic ring; Q is a single bond or a C.sub.1 -C.sub.4 hydrocarbylene diradical; R.sup.1, R.sup.2 and/or Q may be optionally substituted with one or more fluorine atoms; and prodrugs of formula in which one or more of the hydroxy groups are masked as groups which can be reconverted to hydroxy groups in vivo. The compounds show antiinflammatory and immunomodulating effects as well as stong activity in inducing differentiation and inhibiting undesirable proliferation of certain cells.

  本发明涉及以下式的化合物，其中式中X为氢或羟基；R.sup.1和R.sup.2可以相同也可以不同，代表氢或C.sub.1-C.sub.4烃基；或R.sup.1和R.sup.2与携带基团X的碳原子一起形成C.sub.3-C.sub.8环烷基；Q为单键或C.sub.1-C.sub.4烃基亚二基；R.sup.1，R.sup.2和/或Q可以选择性地被一个或多个氟原子取代；以及以下式的前药，其中一个或多个羟基被掩盖为可以在体内重新转化为羟基的基团。该化合物表现出抗炎和免疫调节作用，以及在诱导某些细胞分化和抑制不良增殖方面具有强烈的活性。
• Process for preparing antiosteoporotic agents
  申请人：Hoffman-La Roche Inc.

  公开号：US06255501B1

  公开（公告）日：2001-07-03

  Methods for preparing antiosteoportic agents are disclosed. Compounds useful in the methods are also disclosed.

  本发明公开了制备抗骨质疏松药剂的方法。同时，还公开了在该方法中有用的化合物。
• HYPNOTICS AND ANTICONVULSANTS. I. TERTIARY ACETYLENIC CARBINOLS
  作者：W. M. McLAMORE、M. HARFENIST、A. BAVLEY、S. Y. P'AN

  DOI：10.1021/jo01369a014

  日期：1954.4
• Palladium-Catalyzed Carbon Dioxide Elimination−Fixation Reaction of 4-Methoxycarbonyloxy-2-buten-1-ols
  作者：Masahiro Yoshida、Yusuke Ohsawa、Masataka Ihara

  DOI：10.1021/jo0353280

  日期：2004.3.1

  A new type of palladium-catalyzed CO2 recycling reaction using allylic carbonates is described. Reaction of trans-4-methoxycarbonyloxy-2-buten-1-ols in the presence of a palladium catalyst produces cyclic carbonates having a vinyl group via a CO2 elimination-fixation process. A variety of allylic carbonates participate in the reaction giving cyclic carbonates with high efficiencies. Stereoselective construction of trans-cyclic carbonates is achieved by using nonsymmetric substrates. An enantiospecific reaction proceeds to give chiral cyclic carbonate when a chiral methyl-substituted substrate is subjected to the reaction conditions.