benzyl 2-(phenylthio)propanoate

• 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: benzyl 2-(phenylthio)propanoate
• 英文别名: benzyl 2-phenylsulfanylpropanoate
• 化学式: C₁₆H₁₆O₂S
• 分子量: 272.368
• InChiKey: QFRCBEHYLLRYTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 2-(phenylthio)propanoate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.5h， 生成 丙烯酸苄酯
  参考文献：
  名称：

  Radical Mechanism in the Elimination of 2-Arylsulfinyl Esters

  摘要：

  The mechanism of the dehydrosulfenylation of 2-arylsulfinyl esters was investigated. The reaction was found to follow a homolytic cleavage mechanism as verified by electrospray ionization tandem mass spectrometry and experimental work. Rearranged sulfoxides are obtained as byproduct during the elimination reaction.

  DOI：

  10.1021/jo300699w
• 作为产物：
  描述：

  sodium thiophenolate 、 2-溴丙酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 72.5h， 以70%的产率得到benzyl 2-(phenylthio)propanoate
  参考文献：
  名称：

  Radical Mechanism in the Elimination of 2-Arylsulfinyl Esters

  摘要：

  The mechanism of the dehydrosulfenylation of 2-arylsulfinyl esters was investigated. The reaction was found to follow a homolytic cleavage mechanism as verified by electrospray ionization tandem mass spectrometry and experimental work. Rearranged sulfoxides are obtained as byproduct during the elimination reaction.

  DOI：

  10.1021/jo300699w

文献信息

• Copper-catalyzed enantioselective carbenoid insertion into S–H bonds
  作者：Yong-Zhen Zhang、Shou-Fei Zhu、Yan Cai、Hong-Xiang Mao、Qi-Lin Zhou

  DOI：10.1039/b911670b

  日期：——

  An asymmetric carbenoid insertion into S-H bonds catalyzed by copper-chiral spiro bisoxazoline complexes has been developed, in which a series of alpha-mercaptoesters were produced in high yields with moderate to good enantioselectivities (up to 85% ee); this result represents the best enantioselectivity in the catalytic asymmetric carbenoid S-H bond insertion reaction.

  已开发出由铜-手性螺双恶唑啉配合物催化的不对称类胡萝卜素插入SH键的方法，其中以高收率生产了一系列α-巯基酯，具有中等至良好的对映选择性（高达85％ee）；该结果代表了催化不对称类胡萝卜素SH键插入反应中的最佳对映选择性。
• [1,3] Sigmatropic rearrangement of ketene silyl acetals derived from benzyl α-substituted propanoates
  作者：Isamu Shiina、Hiroshi Nagasue

  DOI：10.1016/s0040-4039(02)01168-1

  日期：2002.8

  A novel [1,3] sigmatropic rearrangement of ketene silyl acetals derived from benzyl α-substituted propanoates is developed. The reaction of ketene silyl acetal derived from optically active 1-phenylethyl 2-methylpropanoate mainly proceeds with the retention of chirality at the benzyl position to give the corresponding optically active silyl ester under thermodynamic conditions.

  开发了一种新的[1,3]衍生自苄基α-取代的丙酸酯的乙烯酮甲硅烷基缩醛的σ重排。衍生自光学活性的2-甲基丙酸1-苯基乙基酯的乙烯酮甲硅烷基乙缩醛的反应主要是在热力学条件下保持手性在苄基位置上得到相应的光学活性的甲硅烷基酯。
• Radical Mechanism in the Elimination of 2-Arylsulfinyl Esters
  作者：Antonio Latorre、Irakusne López、Victoria Ramírez、Santiago Rodríguez、Javier Izquierdo、Florenci V. González、Cristian Vicent

  DOI：10.1021/jo300699w

  日期：2012.6.1

  The mechanism of the dehydrosulfenylation of 2-arylsulfinyl esters was investigated. The reaction was found to follow a homolytic cleavage mechanism as verified by electrospray ionization tandem mass spectrometry and experimental work. Rearranged sulfoxides are obtained as byproduct during the elimination reaction.