S-cyclohexyl (E)-3-phenylprop-2-enethioate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: S-cyclohexyl (E)-3-phenylprop-2-enethioate
• 化学式: C₁₅H₁₈OS
• 分子量: 246.373
• InChiKey: NALQCILQMVGFGJ-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1,1-Diphenyl-1lambda5-phosphacyclopent-5-ene 、 S-cyclohexyl (E)-3-phenylprop-2-enethioate 以 甲苯 为溶剂， 反应 38.0h， 以0.25 g的产率得到trans-[4-(cyclohexylthio)-2-phenyl-4-cyclohepten-1-yl]diphenylphosphine oxide
  参考文献：
  名称：

  Reaction of a Cyclic Phosphonium Ylide with α,β-Unsaturated Thioesters

  摘要：

  The tandem Michael-intramolecular Wittig reactions of a five-membered cyclic phosphonium ylide (2) with alpha,beta-unsaturated thioesters afforded cycloheptene derivatives 4a-g in 29-58% yield. The reaction proceeded via a rigid phosphabicyclic intermediate and supplied the cycloheptene derivatives with high stereoselectivity. On the other hand, although the reaction using S-cyclohexyl cyclopentenethioearboxylate 5a as a substrate gave a 1:1 mixture of cis and trans adducts of the corresponding hydroazulene derivatives, the reaction of S-tert-butyl cyclopentenethiocarboxylate 5b gave cis-adduct as a major product (cis:trans = 17:3).

  DOI：

  10.1021/jo990528q
• 作为产物：
  描述：

  环己硫醇 、 肉桂酸 在 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以80%的产率得到S-cyclohexyl (E)-3-phenylprop-2-enethioate
  参考文献：
  名称：

  Direct thioesterification from carboxylic acids and thiols catalyzed by a Brønsted acid

  摘要：

  在催化量的三氟甲烷磺酸存在下，自由羧酸与自由硫醇直接反应，得到相应的硫酯，并且产率很高。

  DOI：

  10.1039/b109834a

文献信息

• Ligand‐Controlled Regiodivergent Thiocarbonylation of Alkynes toward Linear and Branched α,β‐Unsaturated Thioesters
  作者：Han‐Jun Ai、Wangyang Lu、Xiao‐Feng Wu

  DOI：10.1002/anie.202106079

  日期：2021.7.26

  the synthesis of unsaturated thioesters. A robust ligand-controlled regioselective thiocarbonylation of alkynes is developed. Utilizing boronic acid and 5-chlorosalicylic acid as the acid additive to in situ form 5-chloroborosalicylic acid (5-Cl-BSA), and bis(2-diphenylphosphinophenyl)ether (DPEphos) as the ligand, linear α,β-unsaturated thioesters were produced in a straightforward manner. Switching

  炔烃的硫羰基化为合成不饱和硫酯提供了理想的方法。开发了一种强大的配体控制的炔烃区域选择性硫代羰基化。以硼酸和5-氯水杨酸为酸添加剂，原位生成5-氯硼水杨酸(5-Cl-BSA)，双(2-二苯基膦基苯基)醚(DPEphos)为配体的线性α,β-不饱和硫酯以直接的方式生产。将配体切换为三（2-呋喃基）膦可以改变反应选择性，得到支化产物。值得注意的是，这种方法也代表了内部炔烃的硫代羰基化的第一个例子。
• Palladium-catalyzed alkyne hydrocarbonylation under atmospheric pressure of carbon monoxide in the presence of hydrosilane
  作者：Yu Luo、Xilong Wang、Qianwen Liu、Yimiao He、Jing Li、Shuang Luo、Qiang Zhu

  DOI：10.1039/d2gc04689j

  日期：——

  which is performed under atmospheric pressure of CO in the absence of acids, has been developed. Palladium hydride (Pd-H) generated from triethylsilane (Et3SiH) rather than the traditionally used strong acid (HX) is applied for the first time in this transformation. In addition, an unusual counteranion-controlled linear and branch selectivity for terminal alkynes is observed under otherwise identical

  已经开发出一种用于炔烃烃基化的超温和反应条件，该反应条件是在 CO 大气压下在不存在酸的情况下进行的。由三乙基硅烷 (Et 3 SiH) 而不是传统上使用的强酸 (HX)生成的氢化钯 (Pd-H)首次应用于该转化中。此外，在其他相同条件下观察到不寻常的抗衡阴离子控制的末端炔烃的线性和支化选择性。广泛的 1,1-、1,2- 和 1,2,2-取代的 α,β-不饱和硫酯或酰胺可以区域选择性地从末端和内部炔烃中以中等到极好的收率获得。此外，当使用 2-(叔-丁基）- N -（2-炔基苯基）苯胺作为底物，在 TMS-SYNPHOS 作为手性配体存在下。
• Direct thioesterification from carboxylic acids and thiols catalyzed by a Brønsted acid
  作者：Shinya Iimura、Kei Manabe、Shū Kobayashi

  DOI：10.1039/b109834a

  日期：2002.1.14

  In the presence of a catalytic amount of trifluoromethanesulfonic acid, free carboxylic acids reacted with free thiols directly to afford the corresponding thioesters in high yields.

  在催化量的三氟甲烷磺酸存在下，自由羧酸与自由硫醇直接反应，得到相应的硫酯，并且产率很高。
• Reaction of a Cyclic Phosphonium Ylide with α,β-Unsaturated Thioesters
  作者：Narumi Kishimoto、Tetsuya Fujimoto、Iwao Yamamoto

  DOI：10.1021/jo990528q

  日期：1999.8.1

  The tandem Michael-intramolecular Wittig reactions of a five-membered cyclic phosphonium ylide (2) with alpha,beta-unsaturated thioesters afforded cycloheptene derivatives 4a-g in 29-58% yield. The reaction proceeded via a rigid phosphabicyclic intermediate and supplied the cycloheptene derivatives with high stereoselectivity. On the other hand, although the reaction using S-cyclohexyl cyclopentenethioearboxylate 5a as a substrate gave a 1:1 mixture of cis and trans adducts of the corresponding hydroazulene derivatives, the reaction of S-tert-butyl cyclopentenethiocarboxylate 5b gave cis-adduct as a major product (cis:trans = 17:3).