(E)-2-(3-phenylprop-1-en-1-yl)benzo[b]thiophene | 1334400-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (E)-2-(3-phenylprop-1-en-1-yl)benzo[b]thiophene
• 英文别名: 2-(3-phenylpropenyl)benzo[b]thiophene；2-[(E)-3-phenylprop-1-enyl]-1-benzothiophene
• CAS: 1334400-76-8
• 化学式: C₁₇H₁₄S
• 分子量: 250.364
• InChiKey: YXAVINGFMREWSN-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苯并噻酚-2-羧醛 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium carbonate 、 二甲基苯基磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 15.0h， 生成 (E)-2-(3-phenylprop-1-en-1-yl)benzo[b]thiophene
  参考文献：
  名称：

  镍催化的烯丙醇与有机硼试剂的直接偶联

  摘要：

  已经开发了在催化量的碱的存在下，烯丙基醇与Ni（cod）2催化的芳基硼酸或其衍生物的直接偶联。事实证明，各种各样的烯丙基底物或芳基硼酸都适用于该催化体系。在大多数情况下，本方法不需要使用用于稳定镍催化剂的配体或用于活化烯丙醇的其他活化剂。

  DOI：

  10.1002/cjoc.201800237

文献信息

• Synthesis of Benzothiophene Derivatives by Pd-Catalyzed or Radical-Promoted Heterocyclodehydration of 1-(2-Mercaptophenyl)-2-yn-1-ols
  作者：Bartolo Gabriele、Raffaella Mancuso、Elvira Lupinacci、Lucia Veltri、Giuseppe Salerno、Carla Carfagna

  DOI：10.1021/jo201471k

  日期：2011.10.21

  Novel and convenient approaches to benzothiophene derivatives 3 and 5 have been developed, based on heterocyclization reactions of 1-(2-mercaptophenyl)-2-yn-1-is 2 or 4, respectively, readily available from alkynylation of 2-mercaptobenzaldehydes or 1-(2-mercaptophenyl) ketones 1. In particular, 1-(2-mercaptophenyl)-2-yn-1-ols 2, bearing a CH2R substituent on the triple bond (R = alkyl, aryl), were conveniently converted in fair to good yields (55-82%) into (E)-2-(1-alkenyl)benzothiophenes 3 when allowed to react in the presence of catalytic amounts (2 mol %) of PdI2 in conjunction with KI (KI:PdI2 molar ratio = 10) at 80-100 degrees C in MeCN as the solvent, through a heterocyclodehydration process. On the other hand, 2-alkoxymethylbenzothiophenes 5 were selectively obtained in fair to excellent yields (49-98%) via a radical-promoted substitutive heterocyclodehydration process, by reacting 1-(2-mercaptophenyl)-2-yn-1-ols 4 (bearing an alkyl or aryl substituent on the triple bond) in alcoholic media at 80-100 degrees C in the presence of a radical initiator, such as AIBN.
• Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents
  作者：Gaonan Wang、Yi Gan、Yuanhong Liu

  DOI：10.1002/cjoc.201800237

  日期：2018.10

  The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni(cod)2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or arylboronic acids turned out to be applicable to this catalytic system. The present method does not require the use of ligands for stabilizing the nickel catalyst in most cases or additional

  已经开发了在催化量的碱的存在下，烯丙基醇与Ni（cod）2催化的芳基硼酸或其衍生物的直接偶联。事实证明，各种各样的烯丙基底物或芳基硼酸都适用于该催化体系。在大多数情况下，本方法不需要使用用于稳定镍催化剂的配体或用于活化烯丙醇的其他活化剂。