S-phenyl 2-iodoethanethioate | 67532-83-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-phenyl 2-iodoethanethioate
• 英文别名: S-phenyl α-iodothioacetate；S-Phenyl iodoethanethioate
• CAS: 67532-83-6
• 化学式: C₈H₇IOS
• 分子量: 278.113
• InChiKey: YSEIRMTWYIYLOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-phenyl 2-iodoethanethioate 、 2-萘甲醛 在 三苯基膦 、 magnesium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以78%的产率得到S-phenyl 3-hydroxy-3-(naphthalen-2-yl)propanethioate
  参考文献：
  名称：

  Direct Carbon−Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of α-Halo Thioesters and Enolizable Aldehydes

  摘要：

  The direct addition of enolizable aldehydes and alpha-halo thioesters to produce beta-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic alpha-hydroxy aldehyde derivative is used.

  DOI：

  10.1021/ja1057407
• 作为产物：
  描述：

  S-phenyl 2-bromoethanethioate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以98%的产率得到S-phenyl 2-iodoethanethioate
  参考文献：
  名称：

  Direct carbon–carbon bond formation via soft enolization: aldol addition of α-halogenated thioesters

  摘要：

  α-卤代硫酯在MgBr2·OEt2和i-Pr2NEt存在下经历软烯醇化，并选择性地与醛进行顺式直接醇醛缩合，生成α-卤代-β-羟基硫酯。

  DOI：

  10.1039/c0cc02345k

文献信息

• Boronic Acid Mediated Carbocyanation of Olefins and Vinylation of Alkyl Iodides
  作者：Reina Hara、Chahinaz Khiar、Nitin S. Dange、Pierre Bouillac、Frédéric Robert、Yannick Landais

  DOI：10.1002/ejoc.201800444

  日期：2018.8.15

  The tin‐free carbocyanation of olefins and the addition of alkyl iodides to vinylsulfones were developed by using phenylboronic acid as an aryl radical precursor and tin surrogate. The resulting aryl radical then selectively abstracted an iodine atom from the alkyl iodide to generate a radical that was employed in C–C bond forming processes.

  通过使用苯基硼酸作为芳基自由基前体和锡替代物，开发了烯烃的无锡碳氰化和在乙烯基砜中添加烷基碘的方法。然后，所得的芳基会从烷基碘中选择性地提取出一个碘原子，从而生成一个在CC键形成过程中使用的基团。
• Free-Radical Carbocyanation of Olefins
  作者：Haitham Hassan、Vincent Pirenne、Maren Wissing、Chahinaz Khiar、Ashique Hussain、Frédéric Robert、Yannick Landais

  DOI：10.1002/chem.201605946

  日期：2017.4.3

  The free‐radical three‐component carbocyanation of electron‐rich olefins was investigated with p‐tosyl cyanide as cyanide source. The scope and limitations of the process were established by varying the nature of the alkene and radical precursor. Carbocyanation of chiral allylsilanes was shown to occur with high diastereocontrol, leading to syn β‐silyl nitriles. The origin of the stereocontrol was

  以对甲苯磺酰基氰化物为氰化物源，研究了富电子烯烃的自由基三组分碳氰化反应。通过改变烯烃和自由基前体的性质来确定该方法的范围和局限性。已显示手性烯丙基硅烷的羰基化在非对映异构控制较高的情况下发生，从而导致合成的β-甲硅烷基腈。立体声控制的起源通过Felkin–Anh型过渡状态模型得到了合理化。最后，基于新的烷基磺酰基氰化物的使用，还设计了一种无锡的碳氰化方法，该方法结合了两个碳片段，并要在整个烯烃π系统中添加。
• Free-Radical Carbocyanation of Cyclopropenes: Stereocontrolled Access to All-Carbon Quaternary Stereocenters in Acyclic Systems
  作者：Nitin S. Dange、Frédéric Robert、Yannick Landais

  DOI：10.1021/acs.orglett.6b03163

  日期：2016.12.2

  Free-radical carbocyanation of cyclopropenes offers straightforward access to tetrasubstituted cyclopropanes in satisfying yields with moderate diastereoselectivity. The incorporation of various functional groups on the cyclopropane ring allows a subsequent base-mediated ring-opening reaction leading to functionalized acyclic systems having an all-carbon quaternary stereocenter.

  环丙烯的自由基羰基化可以以令人满意的产率和中等的非对映选择性直接获得四取代的环丙烷。环丙烷环上各种官能团的结合允许随后的碱介导的开环反应，从而导致具有全碳四元立体中心的官能化无环系统。
• Total Synthesis of (±)-Eucophylline. A Free-Radical Approach to the Synthesis of the Azabicyclo[3.3.1]nonane Skeleton
  作者：Haitham Hassan、Shireen Mohammed、Frédéric Robert、Yannick Landais

  DOI：10.1021/acs.orglett.5b02218

  日期：2015.9.18

  The first total synthesis of eucophylline was reported in 10 steps and 10% overall yield. The naphthyridine core of eucophylline was prepared through the coupling between a strained azabicyclo[3.3.1]nonan-2-one and a trisubstituted benzonitrile, followed by a cyclization of the corresponding amidine. This coupling reaction was shown to proceed through a stable bicyclic chloroenamine intermediate. The

  报道了以10个步骤和10％的总收率合成了第一片全合成的优古茶碱。通过在一个应变的氮杂双环[3.3.1]壬南-2-酮和一个三取代的苄腈之间偶联，然后环化相应的prepared，可以制备出真叶菊碱的萘啶核。已表明该偶联反应通过稳定的双环氯亚胺中间体进行。氮杂双环[3.3.1] nonan-2-one骨架又可以通过简单的顺序进入，其中包括自由基三组分烯烃碳氧肟化作为关键步骤。
• Adeno-associated virus (AAV) clades, sequences, vectors containing same, and uses thereof
  申请人：The Trustees of The University of Pennsylvania

  公开号：EP2292780B1

  公开（公告）日：2017-08-23