2,5-dimethyl-3-(phenyl(tosyl)methyl)-1H-indole | 1609115-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,5-dimethyl-3-(phenyl(tosyl)methyl)-1H-indole
• CAS: 1609115-09-4
• 化学式: C₂₄H₂₃NO₂S
• 分子量: 389.518
• InChiKey: CUVGKRCEYWJHMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.93
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  三苯甲硫醇 、 2,5-dimethyl-3-(phenyl(tosyl)methyl)-1H-indole 在 sodium carbonate 、 三乙胺 作用下， 以 水 为溶剂， 反应 12.0h， 生成 2,4-dimethyl-3-(phenyl(tritylthio)methyl)-1H-indole
  参考文献：
  名称：

  磺酰基吲哚的高度对映选择性硫醇化反应，可在水中获得3秒硫取代的吲哚

  摘要：

  提出了在水性介质中由磺酰亚磺酰胺原位产生的乙烯基亚胺中间体对巯基的高度对映选择性有机催化迈克尔加成反应。

  DOI：

  10.1039/c5cc07721d

文献信息

• Catalytic asymmetric coupling of vinylogous species <i>via</i> deconjugated butenolide addition to vinylogous imines <i>in situ</i> generated from arylsulfonyl indoles
  作者：Shu-Pei Yuan、Xia-Yan Zhang、Yun-Qing Jia、Zhen-Hua Wang、Jian-Qiang Zhao、Yong You、Ming-Qiang Zhou、Wei-Cheng Yuan

  DOI：10.1039/d1cc00777g

  日期：——

  An efficient catalytic asymmetric coupling of vinylogous species is developed via deconjugated butenolide addition to vinylogous imines in situ generated from arylsulfonyl indoles. With quinine-derived bifunctional squaramide as the catalyst, a series of structurally diverse enantioenriched sec-alkyl-3-substituted indoles containing valuable γ,γ-disubstituted butenolide moieties and adjacent quaternary-tertiary

  通过向由芳基磺酰基吲哚生成的乙烯基亚胺中解偶联的丁烯内酯加成，开发了乙烯基物质的有效催化不对称偶联。以奎宁为原料的双功能方酰胺为催化剂，可得到一系列结构多样的对映体富集的仲烷基-3-取代的吲哚，其中含有有价值的γ，γ-二取代的丁烯内酯部分和相邻的季-叔立体中心，合成上可行的结果（最高可达97％收率：77：23 dr和97％ee）。
• Combined Di-<i>tert</i>-butyl Peroxide and Inorganic Base Promoted α-Alkylation of Ethers with Arenesulfonylindoles
  作者：Zheng Gu、Yao Tang、Guo-Fang Jiang

  DOI：10.1021/acs.joc.7b00463

  日期：2017.5.19

  The di-tert-butyl peroxide (DTBP) induced coupling of arenesulfonylindoles with ethers such as 1,4-dioxane, tetrahydropyran, tetrahydrofuran, and 1,2-dimethoxyethane was studied. The distinguishing feature of this strategy was characterized by capturing in situ generated vinylogous imine intermediates for the C(sp3)–H bond alkylation of ethers. This general procedure presents the major advantages of

  研究了过氧化二叔丁基（DTBP）诱导的芳烃磺酰吲哚与醚类（例如1,4-二恶烷，四氢吡喃，四氢呋喃和1,2-二甲氧基乙烷）的偶联。该策略的显着特征是捕获原位生成的乙烯基亚胺中间体用于醚的C（sp 3）-H键烷基化。该一般步骤具有底物范围广和官能团相容性好等主要优点
• Catalytic enantioselective hydrophosphinylation of <i>in situ</i>-generated indole-derived vinylogous imines to access 3-(1-diphenylphosphoryl-arylmethyl)indoles
  作者：Yun-Qing Jia、Jian-Qiang Zhao、Zhen-Hua Wang、Yong You、Yan-Ping Zhang、Xin Jin、Ming-Qiang Zhou、Zhen-Zhen Ge、Wei-Cheng Yuan

  DOI：10.1039/d2cc04763b

  日期：——

  An efficient organocatalyzed enantioselective hydrophosphinylation of indole-derived vinylogous imines generated in situ from sulfonyl indoles has been developed. Using quinine-derived bifunctional thiourea as the catalyst, a wide range of structurally diverse chiral 3-(1-diphenylphosphoryl-arylmethyl)indoles were obtained with good to excellent results (up to 99% yield and 99% ee). This method represents

  已经开发了由磺酰基吲哚原位产生的吲哚衍生的插烯亚胺的有效有机催化对映选择性氢膦酰化。使用奎宁衍生的双功能硫脲作为催化剂，获得了多种结构多样的手性 3-(1-二苯基磷酰基-芳甲基)吲哚，并获得了良好至优异的结果（高达 99% 的收率和 99% ee）。该方法代表了氧化膦催化不对称迈克尔加成到乙烯基亚胺中间体的第一个例子。
• The Concise Synthesis of Spiro-Cyclopropane Compounds via the Dearomatization of Indole Derivatives
  作者：Jing Luo、Bo Wu、Mu-Wang Chen、Guo-Fang Jiang、Yong-Gui Zhou

  DOI：10.1021/ol500948r

  日期：2014.5.16

  A concise synthesis of spiro-cyclopropane compounds from indole derivatives and sulfur ylides has been developed via a dearomatization strategy. Moreover, the spiro-cyclopropane compounds could be conveniently transformed to rearomatized indole derivatives in the presence of acids.