3,7-dimethyl-1-pentyl-1H-purine-2,6-(2H,6H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3,7-dimethyl-1-pentyl-1H-purine-2,6-(2H,6H)-dione
• 英文别名: Amyltheobromin；3,7-dimethyl-1-pentylpurine-2,6-dione
• 化学式: C₁₂H₁₈N₄O₂
• 分子量: 250.301
• InChiKey: KJMLJDPUBIPIQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,7-dimethyl-1-pentyl-1H-purine-2,6-(2H,6H)-dione 在 4-二甲氨基吡啶 、 过氧化氢异丙苯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 还原型辅酶II(NADPH)四钠盐 、 cytochrome P₄₅₀ 3A₄ 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (R)-((R)-5-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)pentan-2-yl) 2-methoxy-2-phenylacetate
  参考文献：
  名称：

  Predictable Stereoselective and Chemoselective Hydroxylations and Epoxidations with P450 3A4

  摘要：

  Enantioselective hydroxylation of one specific methylene in the presence of many similar groups is debatably the most challenging chemical transformation. Although chemists have recently made progress toward the hydroxylation of inactivated C-H bonds, enzymes such as P450s (CYPs) remain unsurpassed in specificity and scope. The substrate promiscuity of many P450s is desirable for synthetic applications; however, the inability to predict the products of these enzymatic reactions is impeding advancement. We demonstrate here the utility of a chemical auxiliary to control the selectivity of CYP3A4 reactions. When linked to substrates, inexpensive, achiral theobromine directs the reaction to produce hydroxylation or epoxidation at the fourth carbon from the auxiliary with pro-R facial selectivity. This strategy provides a versatile yet controllable system for regio-, chemo-, and stereoselective oxidations at inactivated C-H bonds and demonstrates the utility of chemical auxiliaries to mediate the activity of highly promiscuous enzymes.

  DOI：

  10.1021/ja200551y
• 作为产物：
  描述：

  可可碱 、 1-溴戊烷 在 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 生成 3,7-dimethyl-1-pentyl-1H-purine-2,6-(2H,6H)-dione
  参考文献：
  名称：

  Highly efficient C-8 oxidation of substituted xanthines with substitution at the 1-, 3-, and 7- positions using biocatalysts

  摘要：

  由克雷伯氏菌属和红球菌属菌株组成的细菌群能将 1-、3- 和 7-取代的黄嘌呤定量转化为各自的 8-氧代化合物。

  DOI：

  10.1039/a900089e

文献信息

• [EN] PROCESS FOR PREPARING AN ENANTIOMERICALLY ENRICHED, DEUTERATED SECONDARY ALCOHOL FROM A CORRESPONDING KETONE WITHOUT REDUCING DEUTERIUM INCORPORATION<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN ALCOOL SECONDAIRE DEUTÉRÉ À ENRICHISSEMENT ÉNANTIOMÉRIQUE À PARTIR D'UNE CÉTONE CORRESPONDANTE SANS RÉDUCTION DE L'INTÉGRATION DE DEUTÉRIUM
  申请人：CONCERT PHARMACEUTICALS INC

  公开号：WO2012031073A1

  公开（公告）日：2012-03-08

  The present invention provides a process for the preparation of enantiomerically enriched, deuterated secondary alcohols of Formula l-A by employing ketoreductases or carbonyl reductases without reducing deuterium incorporation.

  本发明提供了一种制备手性富集的氘代二级醇类化合物l-A的方法，该方法采用酮还原酶或羰基还原酶，而不会降低氘的含量。
• COMPOSITIONS AND METHODS FOR THE TREATMENT OF MULTIPLE SCLEROSIS
  申请人：Cellixbio Private Limited

  公开号：EP2852569B1

  公开（公告）日：2020-10-14
• US4189469A
  申请人：——

  公开号：US4189469A

  公开（公告）日：1980-02-19
• Predictable Stereoselective and Chemoselective Hydroxylations and Epoxidations with P450 3A4
  作者：Aaron T. Larsen、Erin M. May、Karine Auclair

  DOI：10.1021/ja200551y

  日期：2011.5.25

  Enantioselective hydroxylation of one specific methylene in the presence of many similar groups is debatably the most challenging chemical transformation. Although chemists have recently made progress toward the hydroxylation of inactivated C-H bonds, enzymes such as P450s (CYPs) remain unsurpassed in specificity and scope. The substrate promiscuity of many P450s is desirable for synthetic applications; however, the inability to predict the products of these enzymatic reactions is impeding advancement. We demonstrate here the utility of a chemical auxiliary to control the selectivity of CYP3A4 reactions. When linked to substrates, inexpensive, achiral theobromine directs the reaction to produce hydroxylation or epoxidation at the fourth carbon from the auxiliary with pro-R facial selectivity. This strategy provides a versatile yet controllable system for regio-, chemo-, and stereoselective oxidations at inactivated C-H bonds and demonstrates the utility of chemical auxiliaries to mediate the activity of highly promiscuous enzymes.
• Highly efficient C-8 oxidation of substituted xanthines with substitution at the 1-, 3-, and 7- positions using biocatalysts
  作者：K. M. Madyastha、G. R. Sridhar

  DOI：10.1039/a900089e

  日期：——

  A bacterial consortium consisting of strains belonging to the genus Klebsiella and Rhodococcus quantitatively converts 1-, 3- and 7-substituted xanthines to their respective 8-oxo compounds.

  由克雷伯氏菌属和红球菌属菌株组成的细菌群能将 1-、3- 和 7-取代的黄嘌呤定量转化为各自的 8-氧代化合物。