(S)-(-)-1-phenylprop-2-yn-1-yl acetate | 116119-86-9

• 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)-(-)-1-phenylprop-2-yn-1-yl acetate
• 英文别名: (S)-1-phenyl-prop-2-yn-1-ol acetate；(S)-1-phenyl-2-propyn-1-yl acetate；(S)-1-phenylprop-2-yn-1-yl acetate；(S)-phenyl-2-propyn-1-yl acetate；(S)-1-phenylprop-2-ynyl acetate；1-phenyl-2-propynyl acetate；[(1S)-1-phenylprop-2-ynyl] acetate
• CAS: 116119-86-9
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: RIUOEWCMERGVQY-NSHDSACASA-N

物化性质

• 沸点：
  251.0±20.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：

  (S)-(-)-1-phenylprop-2-yn-1-yl acetate 在 lithium aluminium tetrahydride 、 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 19.5h， 生成 (1R,2E,4S)-1-((2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)-4-phenylbut-2-ene-1,4-diol
  参考文献：
  名称：

  1-Phenylprop-2-ynyl Acetate:  A Useful Building Block for the Stereoselective Construction of Polyhydroxylated Chains

  摘要：

  (R)- or (S)-1-phenylprop-2-ynyl acetate was added stereoselectively to aldehydes to afford 4-hydroxy-1-phenylalk-2-ynyl acetates. The transformation of such adducts into the corresponding allylic 1,4-diacetates allowed a highly efficient transfer of chirality from C1 to C3 by a regio- and stereoselective [3,3]-sigmatropic rearrangement. The obtained unsaturated 1,2-diacetates were useful synthetic intermediates whose double bond and/or phenyl group were transformed in different aldehydes, acids, or esters.

  DOI：

  10.1021/ol0616539
• 作为产物：
  描述：

  1-phenylprop-2-ynyl acetate 生成 (S)-(-)-1-phenylprop-2-yn-1-yl acetate
  参考文献：
  名称：

  Aryl propargylic alcohols of high enantiomeric purity via lipase catalyzed resolutions

  摘要：

  A variety of substituted aryl propargylic alcohols were prepared via lipase catalyzed resolutions, the enantioselective hydrolysis of the corresponding esters being the method of choice. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00166-8

文献信息

• Stereocontrol in Palladium-Catalyzed Propargylic Substitutions: Kinetic Resolution to give Enantioenriched 1,5-Enynes and Propargyl Acetates
  作者：Michael J. Ardolino、Meredith S. Eno、James P. Morken

  DOI：10.1002/adsc.201300720

  日期：2013.11.25

  Kinetic resolution during the catalytic allyl-propargyl cross-coupling with chiral starting materials can be accomplished with a chiral Palladium catalyst. These reactions offer ready access to enantiomerically enriched enyne products from simple readily available starting materials.

  与手性原料催化烯丙基-炔丙基交叉偶联过程中的动力学拆分可以通过手性钯催化剂来完成。这些反应可以从简单易得的起始原料中轻松获得对映体富集的烯炔产物。
• Kinetic Resolution of Secondary Alcohols by the Combination of a Chiral Brønsted Acid, DABCO, and Acetyl Chloride
  作者：Hiroki Mandai、Kyouta Murota、Koichi Mitsudo、Seiji Suga

  DOI：10.1021/ol301373x

  日期：2012.7.6

  An efficient and simple protocol for the kinetic resolution of secondary alcohols is presented. The new system is based on a combination of chiral Brønsted acid, DABCO, and acetyl chloride and gives various enantioenriched alcohols with selectivity factors up to 105.

  提出了一种高效简单的仲醇动力学拆分方法。该新系统基于手性布朗斯台德酸，DABCO和乙酰氯的组合，可提供各种对映体富集的醇，选择性系数高达105。
• Gold(I)-Catalyzed Stereoselective Olefin Cyclopropanation
  作者：Magnus J. Johansson、David J. Gorin、Steven T. Staben、F. Dean Toste

  DOI：10.1021/ja0552500

  日期：2005.12.1

  A triphenylphosphinegold(I)-catalyzed cyclopropanation of olefins using propargyl esters as gold(I)-carbene precursors is reported. This reaction provided the basis for the use of a DTBM-SEGPHOS gold(I) complex as a catalyst in the enantioselective (up to 94% ee) preparation of vinyl cyclopropanes with high cis-selectivity.

  报道了使用炔丙酯作为金 (I)-卡宾前体的三苯基膦金 (I) 催化的烯烃环丙烷化反应。该反应为使用 DTBM-SEGPHOS 金（I）配合物作为对映选择性（高达 94% ee）制备具有高顺式选择性乙烯基环丙烷的催化剂奠定了基础。
• Ionic-Surfactant-Coated Burkholderia cepacia Lipase as a Highly Active and Enantioselective Catalyst for the Dynamic Kinetic Resolution of Secondary Alcohols
  作者：Hyunjin Kim、Yoon Kyung Choi、Jusuk Lee、Eungyeong Lee、Jaiwook Park、Mahn-Joo Kim

  DOI：10.1002/anie.201104141

  日期：2011.11.11

  With a coat for activity: A highly active enzyme was prepared by coating Burkholderia cepacia lipase with an ionic surfactant for use in dynamic kinetic resolution (DKR). Important features of this enzyme include: the fastest DKR of 1‐phenylethanol, the highly enantioselective DKR of a wide range of secondary alcohols (RCH(OH)Ar), and the switching of lipase enantioselectivity in DKR depending on the shape

  带有活性涂层：通过用动态动力学拆分（DKR）用离子表面活性剂包被洋葱伯克霍尔德氏菌脂肪酶制备高活性酶。该酶的重要特征包括：1-苯基乙醇的最快DKR，各种仲醇（RCH（OH）Ar）的高对映选择性DKR，以及取决于脂肪链形状的DKR中脂肪酶对映选择性的转换（R）。
• Stereoselective Synthesis of (−)-Spicigerolide
  作者：Yohan Georges、Xavier Ariza、Jordi Garcia

  DOI：10.1021/jo8025753

  日期：2009.3.6

  (-)-Spicigerolide was stereoselectively synthesized from a protected (S)-lactaidehyde. The synthesis of the polyacetylated framework relied on two Zn-mediated stereoselective additions of alkynes to aldehydes as well as a regiocontrolled [3,3]-sigmatropic rearrangement of an allylic acetate. The pyranone moiety was constructed via ring-closing metathesis.

  (-)-Spicigerolide是由保护的(S)-乳糖醛------通过立体选择性合成的。该聚乙酰化框架的合成依赖于两个锌介导的炔烃对醛的二步立体选择性加成，以及一个区域控制的[3,3]-σ迁移重排反应。吡喃酮部分的构建则是通过环闭金属卡宾反应完成。