(S)-3-butyn-2-yl benzoate | 215583-18-9

• 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: (S)-3-butyn-2-yl benzoate
• 英文别名: 3-benzoyloxy-1-butyne；[(2S)-but-3-yn-2-yl] benzoate
• CAS: 215583-18-9
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: MYTIXWPXZCCWOX-VIFPVBQESA-N

物化性质

• 沸点：
  270.7±23.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  triphenylindium 、 (S)-3-butyn-2-yl benzoate 在 双(二苯基膦苯基醚)二氯化钯(II) 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以80%的产率得到丁-1,2-二烯基苯
  参考文献：
  名称：

  钯催化的三有机铟试剂与炔丙基酯的交叉偶联反应。

  摘要：

  [反应：见正文]在钯催化下，三有机铟试剂（R（3）In）通过S（N）2'重排与炔丙基酯反应，从而以高收率和高区域选择性提供丙二烯。反应在室温下与各种R（3）In（芳基，烯基，炔基和甲基）平稳进行。当使用手性，非外消旋的炔丙基酯时，该反应以高的抗立体选择性进行，从而提供了具有高对映体过量的丙二烯。

  DOI：

  10.1021/ol060192o
• 作为产物：
  描述：

  but-3-yn-2-yl benzoate 在 phosphate buffer 、 Pseudomonas lipase Amano AH 、 儿茶提取物 作用下， 反应 48.0h， 生成 (R)-(+)-3-丁炔-2-醇 、 (R)-but-3-yn-2-yl benzoate 、 (S)-3-butyn-2-yl benzoate
  参考文献：
  名称：

  The effect of catechin derivatives on the enantioselectivity of lipase-catalyzed hydrolyses of alkynol benzoate esters

  摘要：

  Polyphenols. such as (+)-catechin and pyrogallol could be used to enhance stereochemical control in the lipase-catalyzed hydrolysis of alkynol benzoate esters, leading to increased enantioselectivities in the kinetic resolution of alkynols with lipase, Amano AH. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00121-0

文献信息

• Stereoselective approach to alk-2-yne-1,4-diols. Application to the synthesis of musclide B
  作者：Marta Amador、Xavier Ariza、Jordi Garcia、Jordi Ortiz

  DOI：10.1016/s0040-4039(02)00395-7

  日期：2002.4

  An expedient method for the stereoselective preparation of alk-2-yne-1,4-diols has been achieved, based on the addition of chiral alk-1-yn-3-ols (or their protected derivatives) to aldehydes mediated by zinc triflate, Et3N, and (+)- or (–)-N-methylephedrine. In general, the configuration observed at the emergent stereocenter depends on the N-methylephedrine employed resulting in good to excellent

  基于将手性烷基-1-yn-3-醇（或其受保护的衍生物）添加到由三氟甲磺酸锌介导的醛中，已经实现了一种立体选择性制备alk-2-yne-1,4-二醇的简便方法，Et 3 N和（+）-或（–）- N-甲基麻黄碱。通常，在新兴的立体中心观察到的构型取决于所使用的N-甲基麻黄碱，从而导致良好的非对映选择性。该策略已应用于对麝香的生物活性代谢产物B的对映选择性合成。
• New Stereoselective Approach to 1,2,3-Triols: Application to a Straight forward Access to Polyoxamic Acid Array
  作者：Xavier Ariza、Jordi Garcia、Jérémie Boyer、Yves Allenbach、Yohan Georges、Mar Vicente

  DOI：10.1055/s-2006-947361

  日期：2006.8

  An efficient approach to alk-4-yne-l,2,3,6-tetraols is described by stereoselective addition of terminal 2-alkyn-1-yl esters to Ley's butane-2,3-diacetal-protected glyceraldehyde. The application of this methodology to a convenient synthesis of (-)-polyoxamic acid derivative is disclosed herein.

  alk-4-yne-1,2,3,6-tetraols 的有效方法是通过立体选择性加成末端 2-alkyn-1-yl 酯到 Ley's 丁烷-2,3-二缩醛保护的甘油醛。本文公开了该方法在(-)-聚肟酸衍生物的方便合成中的应用。
• Ruthenium Hydride-Promoted Dienyl Isomerization: Access to Highly Substituted 1,3-Dienes
  作者：Joseph R. Clark、Justin R. Griffiths、Steven T. Diver

  DOI：10.1021/ja4011207

  日期：2013.3.6

  Ruthenium hydrides were found to promote the positional isomerization of 1,3-dienes into more highly substituted 1,3-dienes in a stereoconvergent manner. The reaction can be conducted in one pot starting with terminal alkynes and alkenes by triggering decomposition of the Grubbs catalyst into a ruthenium hydride, which promotes the dienyl isomerization. The presence of an alcohol additive plays a helpful role in the reaction, significantly increasing the chemical yields. Mechanistic studies are consistent with hydrometalation of the geminally substituted alkene of the 1,3-diene and transit of the ruthenium atom across the diene framework via a pi-allylruthenium intermediate.
• The effect of catechin derivatives on the enantioselectivity of lipase-catalyzed hydrolyses of alkynol benzoate esters
  作者：Kaoru Nakamura、Keishi Takenaka

  DOI：10.1016/s0957-4166(02)00121-0

  日期：2002.3

  Polyphenols. such as (+)-catechin and pyrogallol could be used to enhance stereochemical control in the lipase-catalyzed hydrolysis of alkynol benzoate esters, leading to increased enantioselectivities in the kinetic resolution of alkynols with lipase, Amano AH. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Palladium-Catalyzed Cross-Coupling Reaction of Triorganoindium Reagents with Propargylic Esters
  作者：Ricardo Riveiros、David Rodríguez、José Pérez Sestelo、Luis A. Sarandeses

  DOI：10.1021/ol060192o

  日期：2006.3.1

  [reaction: see text] Triorganoindium reagents (R(3)In) react with propargylic esters under palladium catalysis via an S(N)2' rearrangement to afford allenes in good yields and with high regioselectivity. The reaction proceeds smoothly at room temperature with a variety of R(3)In (aryl, alkenyl, alkynyl, and methyl). When chiral, nonracemic propargylic esters are employed, the reaction takes place with

  [反应：见正文]在钯催化下，三有机铟试剂（R（3）In）通过S（N）2'重排与炔丙基酯反应，从而以高收率和高区域选择性提供丙二烯。反应在室温下与各种R（3）In（芳基，烯基，炔基和甲基）平稳进行。当使用手性，非外消旋的炔丙基酯时，该反应以高的抗立体选择性进行，从而提供了具有高对映体过量的丙二烯。