1-phenyl-1,2,3,4-tetrahydro-β-carboline hydrochloride | 3574-01-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-phenyl-1,2,3,4-tetrahydro-β-carboline hydrochloride
• 英文别名: 1-phenyl-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indole hydrochloride；1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride；1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline hydrochloride；rac-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride；1-Phenyl-2,3,4,9-tetrahydro-1H-β-carbolin; Hydrochlorid；1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline hydrochloride；1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole;hydrochloride
• CAS: 3574-01-4
• 化学式: C₁₇H₁₆N₂*ClH
• 分子量: 284.788
• InChiKey: BPZCTJZLNJOUBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  254-258 °C(Solv: ethanol (64-17-5))

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27.8
• 氢给体数：
  3
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-phenyl-1,2,3,4-tetrahydro-β-carboline hydrochloride 在 sodium carbonate 作用下， 以 水 为溶剂， 生成 1-苯基-2,3,4,9-四氢-1H-beta-咔啉
  参考文献：
  名称：

  通过“底物行走”实现1-芳基四氢-β-咔啉的不对称生物催化合成

  摘要：

  色胺和醛的 Pictet-Spengler 反应的立体选择性催化剂可能允许简单快速地制备手性 1-取代四氢-β-咔啉。尽管生物催化剂以前曾用于皮克泰-斯宾格勒反应，但没有一种生物催化剂接受苯甲醛及其取代衍生物。为了应对这一挑战，结合底物行走和不同野生型主链之间有益突变的转移，将来自萝芙木( Rs STR) 的胡豆苷合酶开发成适合色胺和苯甲醛不对称 Pictet-Spengler 缩合的酶衍生物。双变体Rs STR V176L/V208A 接受各种邻位、间位和对位取代的苯甲醛，并产生相应的手性 1-芳基-四氢-β-咔啉，对映体过量高达 99%。

  DOI：

  10.1002/chem.202004449
• 作为产物：
  描述：

  N-[2-(1H-吲哚-3-基)乙基]苯甲酰胺 在 sodium hydroxide 、 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 乙醇 、 甲苯 、 苯 为溶剂， 反应 3.5h， 生成 1-phenyl-1,2,3,4-tetrahydro-β-carboline hydrochloride
  参考文献：
  名称：

  Hulinska, Hana; Taufmann, Petr; Frycova, Hana, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 2, p. 373 - 380

  摘要：

  DOI：

文献信息

• Microwave-Assisted Synthesis of Tetrahydro-β-carbolines and β-Carbolines
  作者：Scott Eagon、Marc O. Anderson

  DOI：10.1002/ejoc.201301580

  日期：2014.3

  chromatography. This method tolerates a wide range of functionality and can be performed on milligram to gram scales. A subsequent microwave-mediated aromatization of the synthesized tetrahydro-β-carbolines to β-carbolines was also developed utilizing catalytic Pd/C. The aromatization is complete in 60 min or less with most substrates requiring minimal purification.

  开发了一种利用 1,2-二氯乙烷 (DCE) 和三氟乙酸 (TFA) 的微波介导的 Pictet-Spengler 程序，以提供高产率的四氢-β-咔啉盐。反应在 20 分钟或更短的时间内完成，产物以高产率和纯度从溶液中沉淀，无需液-液萃取或柱色谱。这种方法具有广泛的功能，并且可以在毫克到克的范围内进行。随后还利用催化 Pd/C 开发了合成的四氢-β-咔啉到 β-咔啉的后续微波介导的芳构化。芳香化在 60 分钟或更短的时间内完成，大多数底​​物需要最少的纯化。
• Synthesis of β-carbolines via a silver-mediated oxidation of tetrahydro-β-carbolines
  作者：Sierra D. Durham、Brianna Sierra、Maximillian J. Gomez、Jennifer K. Tran、Marc O. Anderson、Nick A. Whittington-Davis、Scott Eagon

  DOI：10.1016/j.tetlet.2017.05.098

  日期：2017.7

  The oxidation of tetrahydro-β-carbolines to β-carbolines using silver carbonate was developed as an alternative to current methods. The oxidation is extremely mild and provides the products in modest to good yields after purification. A number of functional groups are tolerated by this methodology, including reduction-sensitive groups which are often cleaved with other methods. Though the mechanism

  作为目前方法的替代方法，开发了使用碳酸银将四氢-β-咔啉氧化为β-咔啉的方法。氧化非常温和，纯化后产物收率适中，收率良好。该方法容许许多官能团，包括通常用其他方法裂解的还原敏感性基团。尽管尚未完全理解其机理，但反应在开放的烧瓶中进行，对光或湿气不敏感，并为不易通过其他方法制备的化合物提供了可行的合成途径。
• Monoamine Oxidase (MAO-N) Catalyzed Deracemization of Tetrahydro-β-carbolines: Substrate Dependent Switch in Enantioselectivity
  作者：Diego Ghislieri、Deborah Houghton、Anthony P. Green、Simon C. Willies、Nicholas J. Turner

  DOI：10.1021/cs400724g

  日期：2013.12.6

  The tetrahydro-beta-carboline (THBC) ring system is an important structural motif found in a large number of bioactive alkaloid natural products. Herein we report a broadly applicable method for the synthesis of enantiomerically pure beta-carbolines via a deracemization procedure employing the D9 and D11 variants of monoamine oxidase from Aspergillus niger (MAO-N) in combination with a nonselective chemical reducing agent. Biotransformations were performed on a preparative scale, leading to the synthesis of optically enriched products in excellent enantiomeric excess (e.e.; up to 99%) and isolated yield (up to 93%). Interestingly, a switch in enantioselectivity associated with the MAO-N variants is observed as the nature of the C-1 substituent of the THBC is varied. Molecular modeling provided an explanation for this observation and highlighted key active site residues which were modified, resulting in an increase in (R)-selectivity associated with the enzyme. These results provide insight into the factors which influence the selectivity of the MAO-N variants, and may offer a platform for future directed evolution projects aimed toward the challenge of engineering (R)-selective amine oxidase biocatalysts.
• Microwave‐Assisted One‐Pot Preparation of Tetrahydro‐β‐carboline Hydrochlorides under Solvent‐Free Conditions
  作者：Fei Liu、Qi‐Dong You

  DOI：10.1080/00397910701572555

  日期：2007.11

  An efficient and environmentally friendly synthesis of tetrahydro-beta-carboline hydrochlorides via Pictet-Spengler reaction was described. Tryptamine hydrochlorides were used as the reactant and no additional acid catalyst was needed. This reaction was completed within 2.5-9 min in good yield.
• ——
  作者：N. E. Agafonov、A. V. Dudin、A. A. Preobrazhenskii、V. M. Zhulin

  DOI：10.1023/a:1011306517653

  日期：——

  The reactions of aromatic aldehydes with tryptamine (1) in solvents of different polarity were studied. The yields of carbolines in the chosen media decrease with ail increase in the donating properties of the aryl substituent, but they markedly increase at a high pressure (5 kbar), especially for compounds with electron-donating aryl groups. The phase transition of dioxane at 5 kbar also sharply increases the yields of the target products.