1-cyclopropyl-1-(2-(tosylamino)phenyl)methanol | 1334483-49-6

• 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: 1-cyclopropyl-1-(2-(tosylamino)phenyl)methanol
• 英文别名: N-[2-[cyclopropyl(hydroxy)methyl]phenyl]-4-methylbenzenesulfonamide
• CAS: 1334483-49-6
• 化学式: C₁₇H₁₉NO₃S
• 分子量: 317.409
• InChiKey: ZHSORWOYNYINMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-1-(2-(tosylamino)phenyl)methanol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以28%的产率得到N-(2-(cyclopropanecarbonyl)phenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Metal-Free C–H Amination for Indole Synthesis

  摘要：

  An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.

  DOI：

  10.1021/ol5015398
• 作为产物：
  描述：

  2-氨基苯甲醛 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 1-cyclopropyl-1-(2-(tosylamino)phenyl)methanol
  参考文献：
  名称：

  Metal-Free C–H Amination for Indole Synthesis

  摘要：

  An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.

  DOI：

  10.1021/ol5015398

文献信息

• Cyclopropyl Carbinol Rearrangement for Benzo-Fused Nitrogen Ring Synthesis
  作者：Prasath Kothandaraman、Chuhui Huang、Dewi Susanti、Weidong Rao、Philip Wai Hong Chan

  DOI：10.1002/chem.201101363

  日期：2011.8.29

  (Tf=triflate) catalyst, resulting in ionization of the starting material. The tertiary carbocationic intermediate generated in situ in this manner then triggers ring‐opening of the cyclopropane moiety and trapping by the tethered aniline group to give the 2,3‐dihydro‐1H‐benzo[b]azepine. Cyclopropane ring fragmentation of the secondary carbocationic analogue, on the other hand, results in diene formation

  报道了一种合成方法，该方法依靠金催化的2-甲苯磺酰基氨基苯基环丙基甲醇的环丙基甲醇重排反应，以高效地制备2,3-二氢-1 H-苯并[ b ]氮杂和2-乙烯基林多林。该反应显示具有化学选择性，仲醇和叔醇底物分别专门提供苯并稠合的五元和七元环产物。还发现仅在金和银催化剂组合存在的情况下，在温和条件下，成环过程才能以中等至极好的收率进行。据认为，该机理涉及通过（p -CF 3 C 6 H 4）3活化醇PAuCl / AgOTf（Tf =三氟甲磺酸）催化剂，导致原料电离。然后以这种方式原位生成的叔碳正离子中间体触发环丙烷部分的开环并被束缚的苯胺基团捕集，得到2,3-二氢-1 H-苯并[ b ]氮杂pine。另一方面，仲碳阳离子类似物的环丙烷环断裂导致二烯形成，随后进行分子内加氢胺化反应，生成2-乙烯基林多林。
• Ca(NTf ₂ ) ₂ /HFIP‐Mediated Direct and Mild Rearrangement of Cyclopropyl Carbinols to <i>E</i> ‐Homoallylic Triflimides
  作者：Min Wu、Zhiqiang Duan、Qingmei Liu、Hui Gao、Zhi Zhou、Wei Yi、Shengdong Wang

  DOI：10.1002/ejoc.202200813

  日期：2022.9.27

  A novel, general and straightforward Ca(NTf2)2/HFIP-mediated rearrangement of cyclopropyl carbinols for the construction of E-homoallylic triflimides has been developed. In this protocol, Ca(NTf2)2 was used as both the OH activator and the triflimide anion source. This transformation takes place under mild conditions and shows an impressive substrate and functional group tolerance.

  已经开发了一种新颖、通用且直接的 Ca(NTf 2 ) 2 /HFIP 介导的环丙醇重排，用于构建E-高烯丙基三氟酰亚胺。在该协议中，Ca(NTf 2 ) 2被用作 OH 活化剂和 triflimide 阴离子源。这种转化发生在温和的条件下，并显示出令人印象深刻的底物和官能团耐受性。
• 1,3-Migrative Ring Expansion of Spiroindolenines to Azepino[3,4-<i>b</i>]indoles
  作者：Hiroki Tanaka、Toshihiro Yasui、Muhammet Uyanik、Kazuaki Ishihara

  DOI：10.1021/acs.orglett.3c00207

  日期：——

  We serendipitously found an unprecedented 5-to-7-membered ring expansion of 2-alkylspiroindolenines to azepinoindoles mediated by n-tetrabutylammonium fluoride. The starting materials can be easily prepared by the hypoiodite-catalyzed oxidative dearomative spirocyclization of indole derivatives. Mildly basic conditions and electron-deficient protecting groups for the amines were found to be crucial

  我们偶然发现了由正四丁基氟化铵介导的 2-烷基螺吲哚啉到氮杂吲哚的前所未有的 5 至 7 元环扩展。起始原料可以通过次碘酸盐催化的吲哚衍生物的氧化脱芳螺环化反应轻松制备。发现胺的弱碱性条件和缺电子保护基对促进化学选择性反应至关重要。此外，苯胺衍生的螺吲哚啉的环扩展在更温和的条件下仅使用催化量的碳酸铯就可以顺利进行。
• Metal-Free C–H Amination for Indole Synthesis
  作者：Young Ho Jang、So Won Youn

  DOI：10.1021/ol5015398

  日期：2014.7.18

  An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.