(S)-5-phenyl-1-penten-3-yl benzoate

• 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)-5-phenyl-1-penten-3-yl benzoate
• 英文别名: [(3S)-5-phenylpent-1-en-3-yl] benzoate
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: VQKHOPGWLJFMCE-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Benzoic acid (S)-3-phenyl-1-(S)-thiiranyl-propyl ester 在 三乙基硼 、 三正丁基氢锡 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 0.08h， 以85%的产率得到(S)-5-phenyl-1-penten-3-yl benzoate
  参考文献：
  名称：

  硫烷极温和的脱硫；从香叶醇到（+）-和（-）-芳樟醇的有效转化

  摘要：

  三乙基硼烷引发的氢化三丁基锡自由基反应可在-78°C的条件下将硫杂环丁烷高效转化为烯烃。对映体纯的（+）-和（-）-芳樟醇在包括烯烃形成反应在内的四个步骤中从香叶醇衍生而来。

  DOI：

  10.1016/s0040-4039(00)73471-x

文献信息

• Iridium‐Catalyzed Enantioselective Allylic Substitutions of Racemic, Branched Trichloroacetimidates with Heteroatom Nucleophiles: Formation of Allylic C−O, C−N, and C−S Bonds
  作者：Madhawee K. Arachchi、Hien M. Nguyen

  DOI：10.1002/adsc.202100575

  日期：2021.9.7

  branched allylic carbon-heteroatom bonds from racemic, secondary allylic trichloroacetimidates has been developed. The branched allylic substrates undergo dynamic kinetic asymmetric substitution reactions with a number of unactivated anilines and carboxylic acids as well as unactivated aromatic thiols in the presence of a chiral bicyclo[3.3.0]octadiene-ligated iridium catalyst. The allylic C−O, C−N

  已经开发了一种广泛适用的方法，用于从外消旋、仲烯丙基三氯乙酰亚胺酯中区域和对映选择性构建支链烯丙基碳-杂原子键。在手性双环[3.3.0]辛二烯-连接的铱催化剂存在下，支化烯丙基底物与许多未活化的苯胺和羧酸以及未活化的芳族硫醇发生动态动力学不对称取代反应。以合成有用的产率和选择性获得含有烯丙基 C-O、C-N 和 C-S 键的产物。机理研究表明，铱催化的杂原子亲核试剂与烯丙基三氯乙酰亚胺酯底物通过外球亲核加成机制进行对映选择性取代反应。此外，手性二烯连接的铱催化剂可有效促进无环仲苯胺的不对称胺化。重要的是，这种催化铱方法能够使用烷基取代的烯丙基亲电试剂。
• Catalytic Asymmetric Synthesis of Chiral Allylic Esters
  作者：Jeffrey S. Cannon、Stefan F. Kirsch、Larry E. Overman

  DOI：10.1021/ja106685w

  日期：2010.11.3

  A broadly useful catalytic enantioselective synthesis of branched allylic esters from prochiral (Z)-2-alkene-1-ols has been developed. The starting allylic alcohol is converted to its trichloroacetimidate intermediate by reaction with trichloroacetonitrile, either in situ or in a separate step, and this intermediate undergoes clean enantioselective S(N)2' substitution with a variety of carboxylic acids

  已经开发了一种广泛有用的催化对映选择性合成从前手性 (Z)-2-烯烃-1-醇的支链烯丙酯。起始烯丙醇通过与三氯乙腈反应，在原位或在单独的步骤中转化为其三氯乙酰亚胺中间体，并且该中间体在钯的存在下用各种羧酸进行干净的对映选择性 S(N)2' 取代（ II)催化剂(R(p),S)-di-μ-乙酰基双[(η(5)-2-(2'-(4'-甲基乙基)恶唑啉基)环戊二烯基-1-C,3'-N)( η(4)-四苯基环丁二烯)钴]二钯，(R(p),S)-[COP-OAc](2)，或其对映异构体。定义了这种有用的催化不对称烯丙基酯化的范围和限制。
• Ruthenium-Catalyzed Enantioselective Addition of Carboxylic Acids to Allenes
  作者：Jiang-Lin Hu、Felix Bauer、Bernhard Breit

  DOI：10.1021/acscatal.1c03306

  日期：2021.10.1

  A ruthenium-catalyzed synthetic method for branched allylic esters via addition of carboxylic acids to allenes is reported. Ligands were designed and prepared based on the Josiphos skeleton, with which the reaction achieved up to 95% yield and up to >99% enantiomeric excess. A deuterium labeling experiment was performed and a plausible mechanism was proposed. Enantiopure lactones of five- and six-membered

  报道了一种通过将羧酸加成到丙二烯上来合成支链烯丙酯的钌催化合成方法。基于 Josiphos 骨架设计和制备配体，反应产率高达 95%，对映体过量率高达 >99%。进行了氘标记实验并提出了合理的机制。五元环和六元环的对映体纯内酯是通过支链烯丙基酯产物的 RCM 反应合成的。
• Iterative approach to polyketide-type structures: stereoselective synthesis of 1,3-polyols utilizing the catalytic asymmetric Overman esterification
  作者：Jörg T. Binder、Stefan F. Kirsch

  DOI：10.1039/b708248g

  日期：——

  An iterative systematic approach to the 1,3-polyol motif has been developed to provide access to all possible stereoisomers by utilizing the catalytic asymmetric Overman esterification for the construction of all stereogenic centres.

  已经开发出一种针对 1,3-多元醇基序的迭代系统方法，通过利用催化不对称 Overman 酯化来构建所有立体中心，从而提供所有可能的立体异构体。
• Iridium-Catalyzed Kinetic Asymmetric Transformations of Racemic Allylic Benzoates
  作者：Levi M. Stanley、Chen Bai、Mitsuhiro Ueda、John F. Hartwig

  DOI：10.1021/ja103779e

  日期：2010.7.7

  Versatile methods for iridium-catalyzed, kinetic asymmetric substitution of racemic, branched allylic esters are reported. These reactions occur with a variety of aliphatic, aryl, and heteroaryl allylic benzoates to form the corresponding allylic substitution products in high yields (74-96%) with good to excellent enantioselectivity (84-98% ee) with a scope that encompasses a range of anionic carbon and heteroatom nucleophiles. These kinetic asymmetric processes occur with distinct stereochemical courses for racemic aliphatic and aromatic allylic benzoates, and the high reactivity of branched allylic benzoates enables enantioselective allylic substitutions that are slow or poorly selective with linear allylic electrophiles.