tert-butyl 4,5,6,7-tetrahydroindole-1-carboxylate | 186898-96-4

• 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: tert-butyl 4,5,6,7-tetrahydroindole-1-carboxylate
• 英文别名: tert-butyl 4,5,6,7-tetrahydro-1H-indole-1-carboxylate；1,1-dimethylethyl 4,5,6,7-tetrahydro-1H-indole-1-carboxylate；Tert-butyl 4,5,6,7-tetrahydroindole-1-carboxylate
• CAS: 186898-96-4
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: UMMHPHWAKOWGTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenyliodine(III) bis(saccharid) 、 tert-butyl 4,5,6,7-tetrahydroindole-1-carboxylate 在 碘 作用下， 以 氯仿 为溶剂， 反应 21.0h， 以58%的产率得到tert-butyl 2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)-4,5,6,7-tetrahydro-1H-indole-1-carboxylate
  参考文献：
  名称：

  通过可见光和碘的双重引发，杂芳烃的自由基CH-H-胺化

  摘要：

  可以使用预先形成的碘（III）试剂作为氧化剂和氮源的组合来完成新型的杂芳烃的光诱导CH氨基化反应。该反应需要使用少量的分子碘，该分子在光化学活化下会原位生成碘（I）试剂，作为自由基胺化反应的引发剂。共有32个示例说明了转换的广泛范围。

  DOI：

  10.1002/adsc.201800677
• 作为产物：
  描述：

  4,5,6,7-四氢吲哚 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 96.0h， 以93%的产率得到tert-butyl 4,5,6,7-tetrahydroindole-1-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of Functionalized Tropanes by Rhodium(II) Carboxylate-Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Pyrroles

  摘要：

  A series of enantiomerically enriched tropanes was synthesized by the rhodium(II) octanoate-catalyzed reaction of various N-BOC-protected pyrroles with vinyldiazomethanes. The overall 3 + 4 annulation occurs by a tandem cyclopropanation/Cope rearrangement. Asymmetric induction was best achieved in these transformations by using either (S)-lactate or (R)-pantolactone as a chiral auxiliary on the vinyldiazomethanes. Reactions carried out with the chiral catalyst tetrakis[N-( 4-tert-butylbenzenesulfonyl)-(L)-prolinato]dirhodium (2) provided moderate asymmetric induction, but also resulted in the formation of isomeric azabicyclooctane side products. The utility of the synthetic process was demonstrated through the asymmetric synthesis of(-)-anhydroecgonine methyl ester and (-)-ferruginine.

  DOI：

  10.1021/jo961920w

文献信息

• [EN] SUBSTITUTES SULFONYL AZACYCLES AS MODULATORS OF HEDGEHOG (HH) SIGNALLING PATHWAY<br/>[FR] SUBSTITUTS DE SULFONYLAZACYCLES UTILISÉS EN TANT QUE MODULATEURS DE LA VOIE DE SIGNALISATION HEDGEHOG (HH)
  申请人：E THERAPEUTICS PLC

  公开号：WO2019043372A1

  公开（公告）日：2019-03-07

  There are described compounds of formula (I) in which X, R1, R2 and n are each as herein defined; and their use as a medicament in the treatment of conditions involving abnormal activation and/or malfunction of the hedgehog pathway, such as cancer, fibrosis and chronic graft-versus-host disease (c GVHD).

  在公式（I）中描述了化合物，其中X、R1、R2和n分别如本文所定义；以及它们作为药物在治疗涉及异常激活和/或功能障碍的刺猬途径疾病，如癌症、纤维化和慢性移植物抗宿主病（c GVHD）中的用途。
• Asymmetric Synthesis of Tropanes by Rhodium-Catalyzed [4 + 3] Cycloaddition
  作者：Ravisekhara P. Reddy、Huw M. L. Davies

  DOI：10.1021/ja072936e

  日期：2007.8.1

  Rhodium-catalyzed [4 + 3] cycloaddition between methyl 2-(siloxy)vinyldiazoacetate and pyrroles results in the enantioselective synthesis of highly functionalized 8-azabicyclo[3.2.1]octa-2,6-dienes (tropanes). The reaction proceeds via a rhodium−carbenoid intermediate and involves a tandem cyclopropanation/Cope rearrangement mechanism. The optimum chiral dirhodium catalyst for this transformation is

  2-（甲硅烷氧基）乙烯基重氮乙酸甲酯和吡咯之间的铑催化 [4 + 3] 环加成导致对映选择性合成高度官能化的 8-氮杂双环 [3.2.1] octa-2,6-二烯（托烷）。该反应通过铑-类胡萝卜素中间体进行，并涉及串联环丙烷化/Cope 重排机制。这种转化的最佳手性二铑催化剂是金刚烷基甘氨酸衍生的复合物 Rh2(S-PTAD)4。
• 10.1039/d4cc01437e
  作者：Shi, Lin、Liu, Lidong、Lei, Xingyu、Wang, Yihan、Fang, Yeguang、Jiao, Peng

  DOI：10.1039/d4cc01437e

  日期：——

  Dearomative 1,3-dipolar cycloadditions of 1-Boc-pyrroles with in situ generated silver α-bromo alkylidenenitronates delivered a series of 3a,6a-dihydro-4-Boc-pyrrolo[2,3-d]isoxazole-2-oxides (17–91% yields) under very mild conditions. N-Deoxygenation of the cycloaddition product gave a dihydro-pyrrolo[2,3-d]isoxazole, elaborations of which produced various functionalized 2,3-dihydropyrroles and pyrrolidines

  1-Boc-吡咯与原位生成的 α-溴亚烷基亚硝基银的脱芳香 1,3-偶极环加成反应生成一系列 3 a ,6 a -二氢-4-Boc-吡咯并[2,3- d ]异恶唑-2-在非常温和的条件下生成氧化物（17-91% 产率）。环加成产物的N-脱氧得到二氢-吡咯并[2,3 -d ]异恶唑，其精加工产生各种官能化的2,3-二氢吡咯和吡咯烷，展示了我们的吡咯脱芳构化新策略的潜在效用。
• Enantioselective Synthesis of Functionalized Tropanes by Rhodium(II) Carboxylate-Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Pyrroles
  作者：Huw M. L. Davies、Julius J. Matasi、L. Mark Hodges、Nicholas J. S. Huby、Craig Thornley、Norman Kong、Jeffrey H. Houser

  DOI：10.1021/jo961920w

  日期：1997.2.1

  A series of enantiomerically enriched tropanes was synthesized by the rhodium(II) octanoate-catalyzed reaction of various N-BOC-protected pyrroles with vinyldiazomethanes. The overall 3 + 4 annulation occurs by a tandem cyclopropanation/Cope rearrangement. Asymmetric induction was best achieved in these transformations by using either (S)-lactate or (R)-pantolactone as a chiral auxiliary on the vinyldiazomethanes. Reactions carried out with the chiral catalyst tetrakis[N-( 4-tert-butylbenzenesulfonyl)-(L)-prolinato]dirhodium (2) provided moderate asymmetric induction, but also resulted in the formation of isomeric azabicyclooctane side products. The utility of the synthetic process was demonstrated through the asymmetric synthesis of(-)-anhydroecgonine methyl ester and (-)-ferruginine.
• Radical C−H-Amination of Heteroarenes using Dual Initiation by Visible Light and Iodine
  作者：Nicola Lucchetti、Anastasia Tkacheva、Serena Fantasia、Kilian Muñiz

  DOI：10.1002/adsc.201800677

  日期：2018.10.18

  light‐induced C−H amination of heteroarenes can be accomplished with preformed iodine(III) reagents as the combined oxidant and nitrogen source. The reaction requires the use of a small amount of molecular iodine, which under photochemical activation generates in situ an iodine(I) reagent as the initiator of the radical amination reaction. A total of 32 examples exemplify the broad scope of the transformation

  可以使用预先形成的碘（III）试剂作为氧化剂和氮源的组合来完成新型的杂芳烃的光诱导CH氨基化反应。该反应需要使用少量的分子碘，该分子在光化学活化下会原位生成碘（I）试剂，作为自由基胺化反应的引发剂。共有32个示例说明了转换的广泛范围。