1-BOC-5-溴-3-羟基甲基吲哚 | 905710-14-7

• 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
• 中文名称: 1-BOC-5-溴-3-羟基甲基吲哚
• 中文别名: 1-Boc-5-溴-3-羟基甲基吲哚
• 英文名称: tert-butyl 5-bromo-3-(hydroxymethyl)-1H-indole-1-carboxylate
• 英文别名: 1-Boc-5-Bromo-3-hydroxymethylindole；tert-butyl 5-bromo-3-(hydroxymethyl)indole-1-carboxylate
• CAS: 905710-14-7
• 化学式: C₁₄H₁₆BrNO₃
• 分子量: 326.19
• InChiKey: LPXSZZFLLCBIJX-UHFFFAOYSA-N

物化性质

• 熔点：
  105-107 °C
• 沸点：
  442.1±53.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  1-BOC-5-溴-3-羟基甲基吲哚 在 dirhodium(II) tetrakis[(S)-N-phthaloyl-tert-leucinate] 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 tert-butyl 5-bromo-3-(1-(tert-butyldimethylsilyloxy)-3-methoxy-3-oxo-2-phenylpropyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Investigation into Factors Influencing Stereoselectivity in the Reactions of Heterocycles with Donor−Acceptor-Substituted Rhodium Carbenoids

  摘要：

  Rhodium-catalyzed decomposition of aryldiazoacetates in the presence of pyrroles or furans results in mono- or biscyclopropanation of the heterocycle, but with opposite enantioinduction. In the absence of sterically encumbering groups, the cyclopropanation of furan occurs with initial bond formation at the 2-position. If this pathway is sterically blocked, cyclopropanation can occur with initial bond formation at the 3-position of the furan ring; in this case, the cyclopropanation reaction takes place on the opposite face of the heterocycle, and the opposite enantioinduction is observed. Upon extension of this methodology to benzofurans, a highly enantioselective monocyclopropanation reaction occurs to furnish a product derived from initial bond formation at the 2-position of the benzofuran. When this reaction pathway is inhibited by sterically encumbering substituents on the benzofuran, no cyclopropanation of the furan ring is observed, and instead, double cyclopropanation of the benzene ring occurs. Double cyclopropanation of the benzene ring was also observed in reactions with indoles.

  DOI：

  10.1021/jo060779g
• 作为产物：
  描述：

  5-溴-3-甲酰基吲哚-1-羧酸叔丁酯 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以99%的产率得到1-BOC-5-溴-3-羟基甲基吲哚
  参考文献：
  名称：

  Investigation into Factors Influencing Stereoselectivity in the Reactions of Heterocycles with Donor−Acceptor-Substituted Rhodium Carbenoids

  摘要：

  Rhodium-catalyzed decomposition of aryldiazoacetates in the presence of pyrroles or furans results in mono- or biscyclopropanation of the heterocycle, but with opposite enantioinduction. In the absence of sterically encumbering groups, the cyclopropanation of furan occurs with initial bond formation at the 2-position. If this pathway is sterically blocked, cyclopropanation can occur with initial bond formation at the 3-position of the furan ring; in this case, the cyclopropanation reaction takes place on the opposite face of the heterocycle, and the opposite enantioinduction is observed. Upon extension of this methodology to benzofurans, a highly enantioselective monocyclopropanation reaction occurs to furnish a product derived from initial bond formation at the 2-position of the benzofuran. When this reaction pathway is inhibited by sterically encumbering substituents on the benzofuran, no cyclopropanation of the furan ring is observed, and instead, double cyclopropanation of the benzene ring occurs. Double cyclopropanation of the benzene ring was also observed in reactions with indoles.

  DOI：

  10.1021/jo060779g

文献信息

• [EN] ORAL COMPLEMENT FACTOR D INHIBITORS<br/>[FR] INHIBITEURS ORAUX DU FACTEUR D DU COMPLÉMENT
  申请人：BIOCRYST PHARM INC

  公开号：WO2021072198A1

  公开（公告）日：2021-04-15

  Disclosed are compounds of formula (I), and pharmaceutically acceptable salts thereof, which are inhibitors of the complement system. Also provided are pharmaceutical compositions comprising such a compound, and methods of using the compounds and compositions in the treatment or prevention of a disease or condition characterized by aberrant complement system activity.

  揭示了式(I)的化合物及其药学上可接受的盐，这些化合物是裂解系统的抑制剂。还提供了包含这种化合物的药物组合物，以及使用这些化合物和组合物治疗或预防由异常裂解系统活性特征的疾病或状况的方法。
• Ferric Chloride Catalyzed 1,3-Rearrangement of (Phenoxymethyl)heteroarenes to (Heteroarylmethyl)phenols
  作者：Yingzhan Tang、Kaitong Zhuang、Xinhang Zhang、Fukai Xie、Lu Yang、Bin Lin、Maosheng Cheng、Dan Li、Yongxiang Liu

  DOI：10.1002/ejoc.202000419

  日期：2020.6.23

  (Heteroarylmethyl)phenol derivatives were synthesized via a highly useful and robust FeCl3‐catalyzed 1,3‐rearrangement of (phenoxymethyl)arylheterocycles. This strategy features readily available catalyst, mild reaction conditions, short reaction time, and broad substrate scope. The methodology was applied to the synthesis of a key (heteroarylmethyl)phenol intermediate for zafirlukast.

  （杂芳基甲基）苯酚衍生物是通过高度有用且坚固的FeCl 3催化的（苯氧甲基）芳基杂环的1,3-重排而合成的。该策略的特点是催化剂容易获得，反应条件温和，反应时间短，底物范围广。该方法应用于扎鲁司特的关键（杂芳基甲基）苯酚中间体的合成。
• Investigation into Factors Influencing Stereoselectivity in the Reactions of Heterocycles with Donor−Acceptor-Substituted Rhodium Carbenoids
  作者：Simon J. Hedley、Dominic L. Ventura、Paulina M. Dominiak、Cara L. Nygren、Huw M. L. Davies

  DOI：10.1021/jo060779g

  日期：2006.7.1

  Rhodium-catalyzed decomposition of aryldiazoacetates in the presence of pyrroles or furans results in mono- or biscyclopropanation of the heterocycle, but with opposite enantioinduction. In the absence of sterically encumbering groups, the cyclopropanation of furan occurs with initial bond formation at the 2-position. If this pathway is sterically blocked, cyclopropanation can occur with initial bond formation at the 3-position of the furan ring; in this case, the cyclopropanation reaction takes place on the opposite face of the heterocycle, and the opposite enantioinduction is observed. Upon extension of this methodology to benzofurans, a highly enantioselective monocyclopropanation reaction occurs to furnish a product derived from initial bond formation at the 2-position of the benzofuran. When this reaction pathway is inhibited by sterically encumbering substituents on the benzofuran, no cyclopropanation of the furan ring is observed, and instead, double cyclopropanation of the benzene ring occurs. Double cyclopropanation of the benzene ring was also observed in reactions with indoles.